FI80458C - Foerfarande foer framstaellning av . terapeutiskt anvaendbara tiazolo/3,2-a/bensimidazoler och 2,3-dihydroanaloger daerav. - Google Patents
Foerfarande foer framstaellning av . terapeutiskt anvaendbara tiazolo/3,2-a/bensimidazoler och 2,3-dihydroanaloger daerav. Download PDFInfo
- Publication number
- FI80458C FI80458C FI842353A FI842353A FI80458C FI 80458 C FI80458 C FI 80458C FI 842353 A FI842353 A FI 842353A FI 842353 A FI842353 A FI 842353A FI 80458 C FI80458 C FI 80458C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- thiazolo
- pyridyl
- benzimidazole
- Prior art date
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- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 125
- -1 p-phenylphenyl Chemical group 0.000 claims description 35
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 5
- HNQWIEGVHZAQOC-UHFFFAOYSA-N 2-pyridin-2-yl-1,2-dihydro-[1,3]thiazolo[3,2-a]benzimidazole Chemical compound S1C2=NC3=CC=CC=C3N2CC1C1=CC=CC=N1 HNQWIEGVHZAQOC-UHFFFAOYSA-N 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- 125000000335 thiazolyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- WJDGHJWQNMTVPG-UHFFFAOYSA-N 2-(5-ethylpyridin-2-yl)-[1,3]thiazolo[3,2-a]benzimidazole Chemical compound N1=CC(CC)=CC=C1C1=CN2C3=CC=CC=C3N=C2S1 WJDGHJWQNMTVPG-UHFFFAOYSA-N 0.000 claims description 2
- STXMJAJTQAEFNN-UHFFFAOYSA-N 2-pyridin-2-yl-1,2-dihydro-[1,3]thiazolo[3,2-a]benzimidazole 3-oxide Chemical compound C1N(C2=CC=CC=C2N=2)C=2S(=O)C1C1=CC=CC=N1 STXMJAJTQAEFNN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 229920001021 polysulfide Polymers 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- ZLEAFWIYQQKHCF-UHFFFAOYSA-N 6,7-dimethyl-2-pyridin-2-yl-1,2-dihydro-[1,3]thiazolo[3,2-a]benzimidazole 3-oxide Chemical compound C1=2C=C(C)C(C)=CC=2N=C(S2=O)N1CC2C1=CC=CC=N1 ZLEAFWIYQQKHCF-UHFFFAOYSA-N 0.000 claims 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 claims 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 235000013312 flour Nutrition 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000005077 polysulfide Substances 0.000 claims 1
- 150000008117 polysulfides Polymers 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 126
- 239000000203 mixture Substances 0.000 description 57
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 44
- 238000004458 analytical method Methods 0.000 description 37
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 36
- 239000002904 solvent Substances 0.000 description 36
- 239000007787 solid Substances 0.000 description 35
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 18
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- 239000003480 eluent Substances 0.000 description 17
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
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- 239000000377 silicon dioxide Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 239000000284 extract 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
- VPRPVCXSRYFLMR-UHFFFAOYSA-N 2-(1,2-dibromoethyl)pyridine;hydrobromide Chemical compound Br.BrCC(Br)C1=CC=CC=N1 VPRPVCXSRYFLMR-UHFFFAOYSA-N 0.000 description 7
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
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- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
- IHCQWURUZRYCIU-UHFFFAOYSA-N [1,3]thiazolo[3,2-a]benzimidazole Chemical class C1=CC=C2N3C=CSC3=NC2=C1 IHCQWURUZRYCIU-UHFFFAOYSA-N 0.000 description 6
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- 239000007864 aqueous solution Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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- CJGYSWNGNKCJSB-YVLZZHOMSA-N bucladesine Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](OC(=O)CCC)[C@@H]2N1C(N=CN=C2NC(=O)CCC)=C2N=C1 CJGYSWNGNKCJSB-YVLZZHOMSA-N 0.000 description 5
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- 238000007917 intracranial administration Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
- 235000019793 magnesium trisilicate Nutrition 0.000 description 1
- 229940099273 magnesium trisilicate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- ARPRMRNWRRMMMG-UHFFFAOYSA-N methyl 2-pyridin-2-yl-1,2-dihydro-[1,3]thiazolo[3,2-a]benzimidazole-7-carboxylate Chemical compound C1N2C3=CC(C(=O)OC)=CC=C3N=C2SC1C1=CC=CC=N1 ARPRMRNWRRMMMG-UHFFFAOYSA-N 0.000 description 1
- OWOQAGPFQFJSJX-UHFFFAOYSA-N methyl 2-sulfanylidene-1,3-dihydrobenzimidazole-5-carboxylate Chemical compound COC(=O)C1=CC=C2NC(=S)NC2=C1 OWOQAGPFQFJSJX-UHFFFAOYSA-N 0.000 description 1
- YYMRCHLHDPWZNC-UHFFFAOYSA-N methyl 3-oxo-2-pyridin-2-yl-1,2-dihydro-[1,3]thiazolo[3,2-a]benzimidazole-7-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2N=C(S2=O)N1CC2C1=CC=CC=N1 YYMRCHLHDPWZNC-UHFFFAOYSA-N 0.000 description 1
- QOAFDJMGYUCSQL-UHFFFAOYSA-N methyl 6-methyl-2-pyridin-2-yl-1,2-dihydro-[1,3]thiazolo[3,2-a]benzimidazole-7-carboxylate Chemical compound S1C2=NC=3C=C(C)C(C(=O)OC)=CC=3N2CC1C1=CC=CC=N1 QOAFDJMGYUCSQL-UHFFFAOYSA-N 0.000 description 1
- FXMYEUMZYFJQEG-UHFFFAOYSA-N methyl 6-methyl-3-oxo-2-pyridin-2-yl-1,2-dihydro-[1,3]thiazolo[3,2-a]benzimidazole-7-carboxylate Chemical compound O=S1C2=NC=3C=C(C)C(C(=O)OC)=CC=3N2CC1C1=CC=CC=N1 FXMYEUMZYFJQEG-UHFFFAOYSA-N 0.000 description 1
- CWJPDEKMKSNYAI-UHFFFAOYSA-N methyl 7-methyl-2-pyridin-2-yl-1,2-dihydro-[1,3]thiazolo[3,2-a]benzimidazole-6-carboxylate Chemical compound C1N2C=3C=C(C)C(C(=O)OC)=CC=3N=C2SC1C1=CC=CC=N1 CWJPDEKMKSNYAI-UHFFFAOYSA-N 0.000 description 1
- OKQKWZXBUDVWGY-UHFFFAOYSA-N methyl 7-methyl-3-oxo-2-pyridin-2-yl-1,2-dihydro-[1,3]thiazolo[3,2-a]benzimidazole-6-carboxylate Chemical compound C1=2C=C(C)C(C(=O)OC)=CC=2N=C(S2=O)N1CC2C1=CC=CC=N1 OKQKWZXBUDVWGY-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000013014 purified material Substances 0.000 description 1
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8316645 | 1983-06-18 | ||
| GB838316645A GB8316645D0 (en) | 1983-06-18 | 1983-06-18 | Heterocyclic compounds |
| GB8333231 | 1983-12-13 | ||
| GB838333231A GB8333231D0 (en) | 1983-12-13 | 1983-12-13 | Heterocyclic compounds |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI842353A0 FI842353A0 (fi) | 1984-06-11 |
| FI842353L FI842353L (fi) | 1984-12-19 |
| FI80458B FI80458B (fi) | 1990-02-28 |
| FI80458C true FI80458C (fi) | 1990-06-11 |
Family
ID=26286415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI842353A FI80458C (fi) | 1983-06-18 | 1984-06-11 | Foerfarande foer framstaellning av . terapeutiskt anvaendbara tiazolo/3,2-a/bensimidazoler och 2,3-dihydroanaloger daerav. |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0129409B1 (en, 2012) |
| JP (1) | JPS6013794A (en, 2012) |
| KR (1) | KR910009212B1 (en, 2012) |
| AR (2) | AR243895A1 (en, 2012) |
| AT (1) | ATE96441T1 (en, 2012) |
| AU (1) | AU569519B2 (en, 2012) |
| DE (1) | DE3486233T2 (en, 2012) |
| DK (1) | DK296084A (en, 2012) |
| ES (3) | ES8607323A1 (en, 2012) |
| FI (1) | FI80458C (en, 2012) |
| GB (1) | GB2141429B (en, 2012) |
| GR (1) | GR81595B (en, 2012) |
| IE (1) | IE57723B1 (en, 2012) |
| PT (1) | PT78734B (en, 2012) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1341314C (en) | 1984-07-06 | 2001-11-06 | David Cox | Derivatives of benzimidazole, benzothiazole and benzoxazole |
| GB8506657D0 (en) * | 1985-03-14 | 1985-04-17 | Wyeth John & Brother Ltd | Heterocyclic compounds |
| ATE241357T1 (de) * | 1995-09-21 | 2003-06-15 | Pharma Pass Ii Llc | Säurelabile omeprazol enthaltende pharmazeutische zusammensetzung und verfahren zu dessen herstellung |
| US20060024362A1 (en) | 2004-07-29 | 2006-02-02 | Pawan Seth | Composition comprising a benzimidazole and process for its manufacture |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE242226C (en, 2012) * | ||||
| US3704239A (en) * | 1971-03-17 | 1972-11-28 | American Home Prod | Certain thiazole(3,2-a)benzimidazole compounds |
| DE2155415A1 (de) * | 1971-11-08 | 1973-05-17 | Jose Rosan | Verfahren und vorrichtung zur gewinnung eines extrakts aus einer nahrungsmittelsubstanz |
| HU169255B (en, 2012) * | 1973-06-20 | 1976-10-28 | ||
| GB1601335A (en) * | 1978-05-26 | 1981-10-28 | Ruskin B E S | Methods and apparatus for packaging and preparing beverages |
| US4214089A (en) * | 1978-07-18 | 1980-07-22 | American Home Products Corporation | Thiazolo[3,2-a]benzimidazoles, imidazo [2,1-b]thiazoles, and related compounds as antineoplastic agents, and enhancers of the immune response |
| JPS6038396B2 (ja) * | 1979-07-26 | 1985-08-31 | エスエス製薬株式会社 | イミダゾ−ル誘導体及びその製造法 |
| US4293696A (en) * | 1980-12-22 | 1981-10-06 | American Home Products Corporation | 3-Substituted phenylthiazolo[3'2':1,2]imidazo[4,5-b]pyridine-2-alkanoic acids |
| US4376769A (en) * | 1981-06-19 | 1983-03-15 | Schering Corporation | Substituted imidazo thiazoles thiazines, thiazepines and thiazocines |
-
1984
- 1984-05-29 GR GR74859A patent/GR81595B/el unknown
- 1984-06-05 IE IE1399/84A patent/IE57723B1/en unknown
- 1984-06-07 AU AU29177/84A patent/AU569519B2/en not_active Ceased
- 1984-06-11 FI FI842353A patent/FI80458C/fi not_active IP Right Cessation
- 1984-06-14 AT AT84304010T patent/ATE96441T1/de not_active IP Right Cessation
- 1984-06-14 GB GB08415173A patent/GB2141429B/en not_active Expired
- 1984-06-14 EP EP84304010A patent/EP0129409B1/en not_active Expired - Lifetime
- 1984-06-14 DE DE84304010T patent/DE3486233T2/de not_active Expired - Fee Related
- 1984-06-14 PT PT78734A patent/PT78734B/pt not_active IP Right Cessation
- 1984-06-15 DK DK296084A patent/DK296084A/da not_active Application Discontinuation
- 1984-06-16 ES ES533496A patent/ES8607323A1/es not_active Expired
- 1984-06-18 KR KR1019840003415A patent/KR910009212B1/ko not_active Expired
- 1984-06-18 JP JP59126308A patent/JPS6013794A/ja active Granted
-
1985
- 1985-07-16 ES ES545233A patent/ES8702423A1/es not_active Expired
- 1985-07-16 ES ES545234A patent/ES8702424A1/es not_active Expired
-
1987
- 1987-04-07 AR AR87307231A patent/AR243895A1/es active
- 1987-04-07 AR AR87307230A patent/AR242214A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| PT78734B (en) | 1986-06-03 |
| DK296084A (da) | 1984-12-19 |
| DE3486233D1 (de) | 1993-12-02 |
| DE3486233T2 (de) | 1994-03-03 |
| ES8607323A1 (es) | 1986-06-01 |
| GR81595B (en, 2012) | 1984-12-11 |
| FI842353A0 (fi) | 1984-06-11 |
| FI80458B (fi) | 1990-02-28 |
| IE841399L (en) | 1984-12-18 |
| KR910009212B1 (ko) | 1991-11-05 |
| GB2141429B (en) | 1986-12-10 |
| ES8702423A1 (es) | 1987-01-01 |
| EP0129409A3 (en) | 1985-12-18 |
| KR850000461A (ko) | 1985-02-27 |
| JPS6013794A (ja) | 1985-01-24 |
| JPH0564155B2 (en, 2012) | 1993-09-14 |
| AR243895A1 (es) | 1993-09-30 |
| AR242214A1 (es) | 1993-03-31 |
| ES545233A0 (es) | 1987-01-01 |
| PT78734A (pt) | 1985-01-01 |
| IE57723B1 (en) | 1993-03-24 |
| EP0129409B1 (en) | 1993-10-27 |
| ATE96441T1 (de) | 1993-11-15 |
| GB2141429A (en) | 1984-12-19 |
| ES533496A0 (es) | 1986-06-01 |
| FI842353L (fi) | 1984-12-19 |
| DK296084D0 (da) | 1984-06-15 |
| ES545234A0 (es) | 1987-01-01 |
| AU569519B2 (en) | 1988-02-04 |
| EP0129409A2 (en) | 1984-12-27 |
| GB8415173D0 (en) | 1984-07-18 |
| AU2917784A (en) | 1984-12-20 |
| ES8702424A1 (es) | 1987-01-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: JOHN WYETH & BROTHER LIMITED |