SE452765B - Tricykliska imidazolderivat, deras framstellning, farmaceutiska kompositioner och anvendning - Google Patents
Tricykliska imidazolderivat, deras framstellning, farmaceutiska kompositioner och anvendningInfo
- Publication number
- SE452765B SE452765B SE8104941A SE8104941A SE452765B SE 452765 B SE452765 B SE 452765B SE 8104941 A SE8104941 A SE 8104941A SE 8104941 A SE8104941 A SE 8104941A SE 452765 B SE452765 B SE 452765B
- Authority
- SE
- Sweden
- Prior art keywords
- methyl
- formula
- pyridyl
- thio
- benzimidazole
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 21
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims description 16
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title claims 2
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 52
- 239000000203 mixture Substances 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 26
- -1 5-methyl-2-pyridyl Chemical group 0.000 claims description 25
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 8
- 230000027119 gastric acid secretion Effects 0.000 claims description 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
- 208000025865 Ulcer Diseases 0.000 claims description 7
- 231100000397 ulcer Toxicity 0.000 claims description 7
- 239000013543 active substance Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 150000002460 imidazoles Chemical class 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 4
- 238000012546 transfer Methods 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- STLBXFFFISDBMC-UHFFFAOYSA-N 5,5,7,7-tetramethyl-2-(pyridin-2-ylmethylsulfanyl)-3h-cyclopenta[f]benzimidazol-6-one Chemical compound N=1C=2C=C3C(C)(C)C(=O)C(C)(C)C3=CC=2NC=1SCC1=CC=CC=N1 STLBXFFFISDBMC-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- KOAOPAQODUPDDV-UHFFFAOYSA-N 6-[(5-methylpyridin-2-yl)methylsulfinyl]-5h-[1,3]dioxolo[4,5-f]benzimidazole Chemical compound N1=CC(C)=CC=C1CS(=O)C(NC1=C2)=NC1=CC1=C2OCO1 KOAOPAQODUPDDV-UHFFFAOYSA-N 0.000 claims 1
- 239000003699 antiulcer agent Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 63
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 59
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- 239000000243 solution Substances 0.000 description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- 229960000583 acetic acid Drugs 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000012362 glacial acetic acid Substances 0.000 description 27
- 238000002844 melting Methods 0.000 description 27
- 230000008018 melting Effects 0.000 description 27
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 22
- 239000011734 sodium Substances 0.000 description 20
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- 239000007858 starting material Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 239000007868 Raney catalyst Substances 0.000 description 8
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- WGZFUAVVERXXKP-UHFFFAOYSA-N 5,6-diamino-1,1,3,3-tetramethylinden-2-one Chemical compound NC1=C(N)C=C2C(C)(C)C(=O)C(C)(C)C2=C1 WGZFUAVVERXXKP-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 5
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- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
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- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 5
- 239000011593 sulfur Substances 0.000 description 5
- 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
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
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- 238000002474 experimental method Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 4
- MXOPKPMEGUYUCV-UHFFFAOYSA-N 2-(chloromethyl)-5-methylpyridine Chemical compound CC1=CC=C(CCl)N=C1 MXOPKPMEGUYUCV-UHFFFAOYSA-N 0.000 description 3
- SNWQAKNKGGOVMO-UHFFFAOYSA-N 5-nitro-1,3-benzodioxole Chemical compound [O-][N+](=O)C1=CC=C2OCOC2=C1 SNWQAKNKGGOVMO-UHFFFAOYSA-N 0.000 description 3
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- 150000001298 alcohols Chemical class 0.000 description 3
- 230000000767 anti-ulcer Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- PGWHEHZFCSUEMH-UHFFFAOYSA-N 2-[(5-methylpyridin-2-yl)methylsulfanyl]-3,5,6,7-tetrahydrocyclopenta[f]benzimidazole Chemical compound N1=CC(C)=CC=C1CSC(NC1=C2)=NC1=CC1=C2CCC1 PGWHEHZFCSUEMH-UHFFFAOYSA-N 0.000 description 2
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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 |
|---|---|
| SE8104941L SE8104941L (sv) | 1982-02-22 |
| SE452765B true SE452765B (sv) | 1987-12-14 |
Family
ID=4307711
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8104941A SE452765B (sv) | 1980-08-21 | 1981-08-20 | Tricykliska imidazolderivat, deras framstellning, farmaceutiska kompositioner och anvendning |
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) |
Families Citing this family (36)
| 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 |
| SE8300736D0 (sv) * | 1983-02-11 | 1983-02-11 | Haessle Ab | Novel pharmacologically active compounds |
| 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 |
| FR2614618B1 (fr) * | 1987-04-30 | 1989-07-07 | Cird | Derives heterocycliques polycycliques, leur procede de preparation et leur utilisation en medecine humaine et veterinaire |
| 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 |
Family Cites Families (5)
| 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 |
| SE416649B (sv) * | 1974-05-16 | 1981-01-26 | Haessle Ab | Forfarande for framstellning av foreningar som paverkar magsyrasekretionen |
| IN148930B (cg-RX-API-DMAC7.html) * | 1977-09-19 | 1981-07-25 | Hoffmann La Roche | |
| SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
-
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
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 |
| FR2488890A1 (fr) | 1982-02-26 |
| US4554280A (en) | 1985-11-19 |
| 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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