DD262230A5 - Verfahren zur herstellung neuer derivate von 4,5-dihydro-oxazolen - Google Patents
Verfahren zur herstellung neuer derivate von 4,5-dihydro-oxazolen Download PDFInfo
- Publication number
- DD262230A5 DD262230A5 DD87306817A DD30681787A DD262230A5 DD 262230 A5 DD262230 A5 DD 262230A5 DD 87306817 A DD87306817 A DD 87306817A DD 30681787 A DD30681787 A DD 30681787A DD 262230 A5 DD262230 A5 DD 262230A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- formula
- general formula
- dihydro
- compound
- mmol
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical class C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims abstract description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052794 bromium Chemical group 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 229960000583 acetic acid Drugs 0.000 claims description 11
- 239000012362 glacial acetic acid Substances 0.000 claims description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 10
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000007254 oxidation reaction Methods 0.000 claims description 5
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 3
- 150000004967 organic peroxy acids Chemical class 0.000 claims description 3
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 abstract description 5
- 230000027119 gastric acid secretion Effects 0.000 abstract description 4
- 150000003462 sulfoxides Chemical class 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 24
- 239000013078 crystal Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- SKMNWXHVKPVMCW-UHFFFAOYSA-N 5-(4,5-dihydro-1,3-oxazol-2-yl)-1,3-dihydrothieno[2,3-d]imidazole-2-thione Chemical compound S1C=2NC(=S)NC=2C=C1C1=NCCO1 SKMNWXHVKPVMCW-UHFFFAOYSA-N 0.000 description 4
- SBQLYHNEIUGQKH-UHFFFAOYSA-N omeprazole Chemical compound N1=C2[CH]C(OC)=CC=C2N=C1S(=O)CC1=NC=C(C)C(OC)=C1C SBQLYHNEIUGQKH-UHFFFAOYSA-N 0.000 description 4
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- 239000008346 aqueous phase Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- LCJDHJOUOJSJGS-UHFFFAOYSA-N 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridin-1-ium;chloride Chemical compound Cl.COC1=C(C)C=NC(CCl)=C1C LCJDHJOUOJSJGS-UHFFFAOYSA-N 0.000 description 2
- NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 2
- XTBKOFANTANWTK-UHFFFAOYSA-N 2-[2-(pyridin-2-ylmethylsulfanyl)-1h-thieno[2,3-d]imidazol-5-yl]-4,5-dihydro-1,3-oxazole Chemical compound C=1C=CC=NC=1CSC(NC=1C=2)=NC=1SC=2C1=NCCO1 XTBKOFANTANWTK-UHFFFAOYSA-N 0.000 description 2
- VBUADTTWTMWEEG-UHFFFAOYSA-N 2-[2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfanyl]-1h-thieno[2,3-d]imidazol-5-yl]-4,5-dihydro-1,3-oxazole Chemical compound COC1=C(C)C=NC(CSC=2NC=3SC(=CC=3N=2)C=2OCCN=2)=C1C VBUADTTWTMWEEG-UHFFFAOYSA-N 0.000 description 2
- VYPGKBPAXMMBIS-UHFFFAOYSA-N 2-[2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfanyl]-3h-benzimidazol-5-yl]-4,5-dihydro-1,3-oxazole Chemical compound COC1=C(C)C=NC(CSC=2NC3=CC=C(C=C3N=2)C=2OCCN=2)=C1C VYPGKBPAXMMBIS-UHFFFAOYSA-N 0.000 description 2
- SZWWYYXOPBOPPF-UHFFFAOYSA-N 4-(4,5-dihydro-1,3-oxazol-2-yl)-2-nitroaniline Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1C1=NCCO1 SZWWYYXOPBOPPF-UHFFFAOYSA-N 0.000 description 2
- PMMVJUABCIHELF-UHFFFAOYSA-N 4-chloro-n-(2-hydroxyethyl)-3-nitrobenzamide Chemical compound OCCNC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 PMMVJUABCIHELF-UHFFFAOYSA-N 0.000 description 2
- MOIGMXUXOBFNLU-UHFFFAOYSA-N 5-(4,5-dihydro-1,3-oxazol-2-yl)benzimidazole-2-thione Chemical compound C=1C2=NC(=S)N=C2C=CC=1C1=NCCO1 MOIGMXUXOBFNLU-UHFFFAOYSA-N 0.000 description 2
- RDENQVWOYNZEIW-UHFFFAOYSA-N 5-amino-n-(2-chloroethyl)-4-nitrothiophene-2-carboxamide Chemical compound NC=1SC(C(=O)NCCCl)=CC=1[N+]([O-])=O RDENQVWOYNZEIW-UHFFFAOYSA-N 0.000 description 2
- PHPHFQYIWLTXOG-UHFFFAOYSA-N 5-chloro-n-(2-chloroethyl)-4-nitrothiophene-2-carboxamide Chemical compound [O-][N+](=O)C=1C=C(C(=O)NCCCl)SC=1Cl PHPHFQYIWLTXOG-UHFFFAOYSA-N 0.000 description 2
- RLWWLCIJTTTXRJ-UHFFFAOYSA-N 5-chloro-n-(2-hydroxyethyl)-4-nitrothiophene-2-carboxamide Chemical compound OCCNC(=O)C1=CC([N+]([O-])=O)=C(Cl)S1 RLWWLCIJTTTXRJ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- -1 Methoxy, ethoxy, propyloxy, isopropyloxy, butyloxy Chemical group 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
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- 238000005984 hydrogenation reaction Methods 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- XVVKPURRUPCOHQ-UHFFFAOYSA-N 2-(4-chloro-3-nitrophenyl)-4,5-dihydro-1,3-oxazole Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C=2OCCN=2)=C1 XVVKPURRUPCOHQ-UHFFFAOYSA-N 0.000 description 1
- PBDFBZPTRXMFBL-UHFFFAOYSA-N 2-(chloromethyl)-4-methoxypyridine;hydrochloride Chemical compound Cl.COC1=CC=NC(CCl)=C1 PBDFBZPTRXMFBL-UHFFFAOYSA-N 0.000 description 1
- QTYKJVJJSBDMCC-UHFFFAOYSA-N 2-[2-(pyridin-2-ylmethylsulfanyl)-3h-benzimidazol-5-yl]-4,5-dihydro-1,3-oxazole Chemical compound C=1C=CC=NC=1CSC(NC1=CC=2)=NC1=CC=2C1=NCCO1 QTYKJVJJSBDMCC-UHFFFAOYSA-N 0.000 description 1
- DCSXSRBTEVTFAY-UHFFFAOYSA-N 2-[2-(pyridin-2-ylmethylsulfinyl)-1h-thieno[2,3-d]imidazol-5-yl]-4,5-dihydro-1,3-oxazole Chemical compound N=1C=2SC(C=3OCCN=3)=CC=2NC=1S(=O)CC1=CC=CC=N1 DCSXSRBTEVTFAY-UHFFFAOYSA-N 0.000 description 1
- OFPUAQDJLPMNKL-UHFFFAOYSA-N 2-[2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-3h-benzimidazol-5-yl]-4,5-dihydro-1,3-oxazole Chemical compound COC1=C(C)C=NC(CS(=O)C=2NC3=CC=C(C=C3N=2)C=2OCCN=2)=C1C OFPUAQDJLPMNKL-UHFFFAOYSA-N 0.000 description 1
- BUSMPHWTVZDIDV-UHFFFAOYSA-N 2-[2-[(4-methoxypyridin-2-yl)methylsulfanyl]-1h-thieno[2,3-d]imidazol-5-yl]-4,5-dihydro-1,3-oxazole Chemical compound COC1=CC=NC(CSC=2NC=3SC(=CC=3N=2)C=2OCCN=2)=C1 BUSMPHWTVZDIDV-UHFFFAOYSA-N 0.000 description 1
- SKQCJXFWNABFRR-UHFFFAOYSA-N 2-[2-[(4-methoxypyridin-2-yl)methylsulfanyl]-3h-benzimidazol-5-yl]-4,5-dihydro-1,3-oxazole Chemical compound COC1=CC=NC(CSC=2NC3=CC(=CC=C3N=2)C=2OCCN=2)=C1 SKQCJXFWNABFRR-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- JMHKRFZCFRFNJS-UHFFFAOYSA-N 4-chloro-n-(2-chloroethyl)-3-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC(C(=O)NCCCl)=CC=C1Cl JMHKRFZCFRFNJS-UHFFFAOYSA-N 0.000 description 1
- LIJYDUXAVSRNAQ-UHFFFAOYSA-N 5-(4,5-dihydro-1,3-oxazol-2-yl)-1,3-dihydrobenzimidazole-2-thione Chemical compound C1=C2NC(=S)NC2=CC=C1C1=NCCO1 LIJYDUXAVSRNAQ-UHFFFAOYSA-N 0.000 description 1
- DFXQXFGFOLXAPO-UHFFFAOYSA-N 96-99-1 Chemical compound OC(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 DFXQXFGFOLXAPO-UHFFFAOYSA-N 0.000 description 1
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
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- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
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- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT243786 | 1986-09-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD262230A5 true DD262230A5 (de) | 1988-11-23 |
Family
ID=3534337
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD87306817A DD262230A5 (de) | 1986-09-10 | 1987-09-09 | Verfahren zur herstellung neuer derivate von 4,5-dihydro-oxazolen |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4818760A (cs) |
| EP (1) | EP0261478B1 (cs) |
| JP (1) | JPS6377878A (cs) |
| KR (1) | KR880003941A (cs) |
| AT (1) | ATE62908T1 (cs) |
| AU (1) | AU596869B2 (cs) |
| CA (1) | CA1256109A (cs) |
| CS (1) | CS268191B2 (cs) |
| DD (1) | DD262230A5 (cs) |
| DE (1) | DE3769563D1 (cs) |
| DK (1) | DK165322C (cs) |
| ES (1) | ES2028838T3 (cs) |
| FI (1) | FI89267C (cs) |
| GR (1) | GR3001842T3 (cs) |
| HU (1) | HU198059B (cs) |
| MY (1) | MY102003A (cs) |
| NO (1) | NO165195C (cs) |
| NZ (1) | NZ221723A (cs) |
| SG (1) | SG39892G (cs) |
| SU (1) | SU1574177A3 (cs) |
| ZA (1) | ZA876740B (cs) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US6852739B1 (en) | 1999-02-26 | 2005-02-08 | Nitromed Inc. | Methods using proton pump inhibitors and nitric oxide donors |
| US7794752B1 (en) | 1999-06-07 | 2010-09-14 | Nycomed Gmbh | Preparation and administration form comprising an acid-labile active compound |
| EP1534278A4 (en) * | 2002-08-01 | 2006-09-06 | Nitromed Inc | NITROSED PROTONATE PUMP INHIBITORS, COMPOSITIONS AND USE METHOD |
| US8802139B2 (en) * | 2003-06-26 | 2014-08-12 | Intellipharmaceutics Corp. | Proton pump-inhibitor-containing capsules which comprise subunits differently structured for a delayed release of the active ingredient |
| PT1746980E (pt) * | 2004-05-07 | 2012-01-25 | Nycomed Gmbh | Forma de dosagem farmacêutica compreendendo granulados assim como o seu processo de fabrico |
| US8394409B2 (en) | 2004-07-01 | 2013-03-12 | Intellipharmaceutics Corp. | Controlled extended drug release technology |
| US10624858B2 (en) | 2004-08-23 | 2020-04-21 | Intellipharmaceutics Corp | Controlled release composition using transition coating, and method of preparing same |
| US10064828B1 (en) | 2005-12-23 | 2018-09-04 | Intellipharmaceutics Corp. | Pulsed extended-pulsed and extended-pulsed pulsed drug delivery systems |
| EP2007360B1 (en) * | 2006-04-03 | 2014-11-26 | Isa Odidi | Controlled release delivery device comprising an organosol coat |
| US10960077B2 (en) | 2006-05-12 | 2021-03-30 | Intellipharmaceutics Corp. | Abuse and alcohol resistant drug composition |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4045564A (en) * | 1974-02-18 | 1977-08-30 | Ab Hassle | Benzimidazole derivatives useful as gastric acid secretion inhibitors |
| SE7804231L (sv) * | 1978-04-14 | 1979-10-15 | Haessle Ab | Magsyrasekretionsmedel |
| GB8305245D0 (en) * | 1983-02-25 | 1983-03-30 | Fujisawa Pharmaceutical Co | Imidazo-heterocyclic compounds |
| SE8404065D0 (sv) * | 1984-08-10 | 1984-08-10 | Haessle Ab | Novel biologically active compounds |
| FI861772L (fi) * | 1985-05-07 | 1986-11-08 | Chemie Linz Ag | Nya tieno(2,3-d)imidazolderivat och foerfarande for deras framstaellning. |
| DE3777855D1 (de) * | 1986-02-20 | 1992-05-07 | Hoechst Ag | Substituierte thienoimidazol-derivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung als magensaeuresekretionshemmer. |
-
1987
- 1987-09-03 CA CA000546073A patent/CA1256109A/en not_active Expired
- 1987-09-04 EP EP87112928A patent/EP0261478B1/de not_active Expired - Lifetime
- 1987-09-04 DE DE8787112928T patent/DE3769563D1/de not_active Expired - Fee Related
- 1987-09-04 AT AT87112928T patent/ATE62908T1/de not_active IP Right Cessation
- 1987-09-04 ES ES198787112928T patent/ES2028838T3/es not_active Expired - Lifetime
- 1987-09-07 NO NO873722A patent/NO165195C/no unknown
- 1987-09-07 MY MYPI87001580A patent/MY102003A/en unknown
- 1987-09-08 NZ NZ221723A patent/NZ221723A/xx unknown
- 1987-09-08 CS CS876497A patent/CS268191B2/cs unknown
- 1987-09-08 AU AU78170/87A patent/AU596869B2/en not_active Ceased
- 1987-09-09 DD DD87306817A patent/DD262230A5/de not_active IP Right Cessation
- 1987-09-09 DK DK469687A patent/DK165322C/da not_active IP Right Cessation
- 1987-09-09 HU HU874022A patent/HU198059B/hu not_active IP Right Cessation
- 1987-09-09 KR KR870009953A patent/KR880003941A/ko not_active Ceased
- 1987-09-09 FI FI873892A patent/FI89267C/fi not_active IP Right Cessation
- 1987-09-09 ZA ZA876740A patent/ZA876740B/xx unknown
- 1987-09-09 US US07/094,594 patent/US4818760A/en not_active Expired - Fee Related
- 1987-09-09 SU SU874203301A patent/SU1574177A3/ru active
- 1987-09-10 JP JP62225453A patent/JPS6377878A/ja active Pending
-
1991
- 1991-04-25 GR GR90401062T patent/GR3001842T3/el unknown
-
1992
- 1992-04-11 SG SG398/92A patent/SG39892G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK469687A (da) | 1988-03-11 |
| HU198059B (en) | 1989-07-28 |
| KR880003941A (ko) | 1988-05-31 |
| AU596869B2 (en) | 1990-05-17 |
| NO873722D0 (no) | 1987-09-07 |
| DK165322B (da) | 1992-11-09 |
| EP0261478A1 (de) | 1988-03-30 |
| ES2028838T3 (es) | 1992-07-16 |
| CA1256109A (en) | 1989-06-20 |
| DK469687D0 (da) | 1987-09-09 |
| SU1574177A3 (ru) | 1990-06-23 |
| SG39892G (en) | 1992-10-02 |
| NZ221723A (en) | 1989-11-28 |
| NO165195B (no) | 1990-10-01 |
| NO165195C (no) | 1991-01-09 |
| NO873722L (no) | 1988-03-11 |
| DE3769563D1 (de) | 1991-05-29 |
| MY102003A (en) | 1992-02-29 |
| AU7817087A (en) | 1988-03-17 |
| ATE62908T1 (de) | 1991-05-15 |
| JPS6377878A (ja) | 1988-04-08 |
| HUT47288A (en) | 1989-02-28 |
| GR3001842T3 (en) | 1992-11-23 |
| FI873892A0 (fi) | 1987-09-09 |
| DK165322C (da) | 1993-03-29 |
| EP0261478B1 (de) | 1991-04-24 |
| ZA876740B (en) | 1988-03-14 |
| CS649787A2 (en) | 1989-05-12 |
| US4818760A (en) | 1989-04-04 |
| FI873892L (fi) | 1988-03-11 |
| CS268191B2 (en) | 1990-03-14 |
| FI89267B (fi) | 1993-05-31 |
| FI89267C (fi) | 1993-09-10 |
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| Date | Code | Title | Description |
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| ENJ | Ceased due to non-payment of renewal fee |