NO834773L - Substituerte fenylsulfonyloksybenzimidazolkarbaminater, fremgangsmaate til deres fremstilling og deres anvendelse som legemiddel - Google Patents
Substituerte fenylsulfonyloksybenzimidazolkarbaminater, fremgangsmaate til deres fremstilling og deres anvendelse som legemiddelInfo
- Publication number
- NO834773L NO834773L NO834773A NO834773A NO834773L NO 834773 L NO834773 L NO 834773L NO 834773 A NO834773 A NO 834773A NO 834773 A NO834773 A NO 834773A NO 834773 L NO834773 L NO 834773L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- substituted
- atoms
- benzimidazole
- phenylsulfonyloxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 238000002360 preparation method Methods 0.000 title claims description 6
- QABSAPZPFVUVJP-UHFFFAOYSA-N 1h-benzimidazol-2-yl benzenesulfonate Chemical class N=1C2=CC=CC=C2NC=1OS(=O)(=O)C1=CC=CC=C1 QABSAPZPFVUVJP-UHFFFAOYSA-N 0.000 title 1
- -1 1,1,2,2-tetrafluoroethoxy Chemical group 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- IJFIOSOCUKKJTP-UHFFFAOYSA-N 1h-benzimidazol-2-yl benzenesulfonate;carbamic acid Chemical class NC(O)=O.N=1C2=CC=CC=C2NC=1OS(=O)(=O)C1=CC=CC=C1 IJFIOSOCUKKJTP-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 150000004987 o-phenylenediamines Chemical class 0.000 claims description 7
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- BHFLSZOGGDDWQM-UHFFFAOYSA-N 1h-benzimidazole;carbamic acid Chemical compound NC(O)=O.C1=CC=C2NC=NC2=C1 BHFLSZOGGDDWQM-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 244000000013 helminth Species 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- 125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- 238000000354 decomposition reaction Methods 0.000 description 12
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- 238000003756 stirring Methods 0.000 description 6
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- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- ZVIDWFUBDDXAJA-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-fluorobenzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=C(F)C=C1 ZVIDWFUBDDXAJA-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- RPZYNDSYJSJYCC-UHFFFAOYSA-N (3,4-diaminophenyl) 4-fluorobenzenesulfonate Chemical compound C1=C(N)C(N)=CC=C1OS(=O)(=O)C1=CC=C(F)C=C1 RPZYNDSYJSJYCC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000000507 anthelmentic effect Effects 0.000 description 3
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- 150000002431 hydrogen Chemical class 0.000 description 3
- 150000007529 inorganic bases Chemical class 0.000 description 3
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- 238000010992 reflux Methods 0.000 description 3
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- 239000008096 xylene Substances 0.000 description 3
- OIWPFXFMZOMJCR-UHFFFAOYSA-N (2-amino-3h-benzimidazol-5-yl) 4-fluorobenzenesulfonate Chemical compound C1=C2NC(N)=NC2=CC=C1OS(=O)(=O)C1=CC=C(F)C=C1 OIWPFXFMZOMJCR-UHFFFAOYSA-N 0.000 description 2
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- 241001465754 Metazoa Species 0.000 description 2
- UINGPWWYGSJYAY-UHFFFAOYSA-N Methyl 5-hydroxy-2-benzimidazole carbamate Chemical compound C1=C(O)C=C2NC(NC(=O)OC)=NC2=C1 UINGPWWYGSJYAY-UHFFFAOYSA-N 0.000 description 2
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- 241000545744 Hirudinea Species 0.000 description 1
- 241001547406 Hyostrongylus Species 0.000 description 1
- 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000243789 Metastrongyloidea Species 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 241000510960 Oesophagostomum Species 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000242541 Trematoda Species 0.000 description 1
- 241000243797 Trichostrongylus Species 0.000 description 1
- MNMRILVWKNBQMF-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 3-bromo-4-fluorobenzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C1=CC=C(F)C(Br)=C1 MNMRILVWKNBQMF-UHFFFAOYSA-N 0.000 description 1
- NHGCIPXCUDYTRT-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 3-fluorobenzenesulfonate Chemical compound C=1C=C2NC(NC(=O)OC)=NC2=CC=1OS(=O)(=O)C1=CC=CC(F)=C1 NHGCIPXCUDYTRT-UHFFFAOYSA-N 0.000 description 1
- OLXAJKZYCBLENA-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-cycloheptylbenzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C(C=C1)=CC=C1C1CCCCCC1 OLXAJKZYCBLENA-UHFFFAOYSA-N 0.000 description 1
- OXLUNAGFVMRVMP-UHFFFAOYSA-N [2-(methoxycarbonylamino)-3h-benzimidazol-5-yl] 4-cyclopentylbenzenesulfonate Chemical compound C1=C2NC(NC(=O)OC)=NC2=CC=C1OS(=O)(=O)C(C=C1)=CC=C1C1CCCC1 OXLUNAGFVMRVMP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- YHMFTWZCHPQXRM-UHFFFAOYSA-N dichloromethylidenecarbamic acid Chemical class OC(=O)N=C(Cl)Cl YHMFTWZCHPQXRM-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- VYGLVTTUPFVKBJ-UHFFFAOYSA-N fluorobenzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.FC1=CC=CC=C1 VYGLVTTUPFVKBJ-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- IUROBCDXAGBTOV-UHFFFAOYSA-N methyl n-(dichloromethylidene)carbamate Chemical compound COC(=O)N=C(Cl)Cl IUROBCDXAGBTOV-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical class N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 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
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823247615 DE3247615A1 (de) | 1982-12-23 | 1982-12-23 | Substituierte phenylsulfonyloxybenzimidazolcarbaminate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO834773L true NO834773L (no) | 1984-06-25 |
Family
ID=6181486
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO834773A NO834773L (no) | 1982-12-23 | 1983-12-22 | Substituerte fenylsulfonyloksybenzimidazolkarbaminater, fremgangsmaate til deres fremstilling og deres anvendelse som legemiddel |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4639463A (fr) |
| EP (1) | EP0115039B1 (fr) |
| JP (1) | JPS59118774A (fr) |
| KR (1) | KR910000045B1 (fr) |
| AR (1) | AR241017A1 (fr) |
| AT (1) | ATE32459T1 (fr) |
| AU (1) | AU558902B2 (fr) |
| CA (1) | CA1199642A (fr) |
| DE (2) | DE3247615A1 (fr) |
| DK (1) | DK150065C (fr) |
| ES (1) | ES8406448A1 (fr) |
| FI (1) | FI834709A (fr) |
| GR (1) | GR79454B (fr) |
| HU (1) | HU192972B (fr) |
| IL (1) | IL70520A (fr) |
| MA (1) | MA19985A1 (fr) |
| MY (1) | MY100900A (fr) |
| NO (1) | NO834773L (fr) |
| NZ (1) | NZ206658A (fr) |
| PH (1) | PH21374A (fr) |
| PT (1) | PT77876B (fr) |
| ZA (1) | ZA839534B (fr) |
| ZM (1) | ZM9283A1 (fr) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9115272D0 (en) * | 1991-07-15 | 1991-08-28 | Pfizer Ltd | Benzimidazole anthelmintics |
| GB9115273D0 (en) * | 1991-07-15 | 1991-08-28 | Pfizer Ltd | Benzimidazole anthelmintics |
| GB9124002D0 (en) * | 1991-11-12 | 1992-01-02 | Pfizer Ltd | Benzimidazole anthelmintic agents |
| SE9103745D0 (sv) * | 1991-12-18 | 1991-12-18 | Wikstroem Haakan | Aryl-triflates and related compounds |
| GB0100889D0 (en) | 2001-01-12 | 2001-02-21 | Oxford Glycosciences Uk Ltd | Compounds |
| EP1298125A1 (fr) | 2001-09-26 | 2003-04-02 | Aventis Pharma S.A. | Benzimidazoles substitués et leur usage comme traitement du cancer |
| EP1534676B1 (fr) * | 2002-07-17 | 2012-09-12 | Actelion Pharmaceuticals Ltd. | Utilisation de derives du piperidinetriol en tant qu'inhibiteurs de la glycosylceramide synthase |
| JP4585851B2 (ja) * | 2002-07-17 | 2010-11-24 | アクテリオン ファーマシューティカルズ リミテッド | グルコシルセラミドシンターゼの阻害剤としてのピペリジントリオール誘導体 |
| GB0313678D0 (en) * | 2003-06-13 | 2003-07-16 | Oxford Glycosciences Uk Ltd | Novel compounds |
| GB0313677D0 (en) * | 2003-06-13 | 2003-07-16 | Oxford Glycosciences Uk Ltd | Novel compound |
| FR2868421B1 (fr) | 2004-04-01 | 2008-08-01 | Aventis Pharma Sa | Nouveaux benzothiazoles et leur utilisation comme medicaments |
| WO2007014846A1 (fr) * | 2005-07-28 | 2007-02-08 | Intervet International B.V. | Nouveaux benzimidazolyl(thio)carbamates ayant une activité antiparasitaire et synthèse de ceux-ci |
| FR2891273B1 (fr) | 2005-09-27 | 2007-11-23 | Aventis Pharma Sa | NOUVEAUX DERIVES BENZIMIDAZOLES ET BENZOTHIAZOLES, LEUR PREPARATION ET LEUR UTILISATION PHARMACEUTIQUE NOTAMMENT COMME INHIBITEURS DE CMet |
| AU2007345301A1 (en) * | 2006-06-12 | 2008-07-31 | Smith And Nephew Inc | Systems, methods and devices for tibial resection |
| PL2037914T3 (pl) | 2006-06-14 | 2014-04-30 | Intervet Int Bv | Zawiesina zawierająca karbaminian benzoimidazolu i polisorbat |
| CN1966495B (zh) * | 2006-09-15 | 2010-06-16 | 常州亚邦齐晖医药化工有限公司 | 制备5-(4-氟苯磺酰氧基)苯并咪唑-2-氨基甲酸甲酯的方法 |
| CN102060780B (zh) * | 2010-12-27 | 2014-11-05 | 雅本化学股份有限公司 | 2-(n-取代)-氨基苯并咪唑衍生物的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE54507C (de) * | F. A. LAESECKE in Leipzig | Zerlegbarer Rüstbock | ||
| CA562096A (fr) * | 1958-08-19 | J. Cavallito Chester | Sels d'ammonium quaternaire de derives de pyridindole | |
| GB764232A (en) * | 1954-02-12 | 1956-12-19 | Irwin Neisler And Company | Quaternary ammonium salts of pyridindole derivatives |
| ES273769A1 (es) * | 1961-01-18 | 1962-06-01 | Geigy Ag J R | Procedimiento para la preparaciën de nuevos derivados de amidas de acido beta-carbolin-carboxilico |
| DE2441201C2 (de) * | 1974-08-28 | 1986-08-07 | Hoechst Ag, 6230 Frankfurt | Anthelminthisch wirksame 2-Carbalkoxyamino-5(6)-phenyl-sulfonyloxy-benzimidazole und Verfahren zu ihrer Herstellung |
| JPS5914027B2 (ja) * | 1976-02-27 | 1984-04-02 | ヘキスト・アクチ−エンゲゼルシヤフト | ２−カルボアルコキシアミノ−５（６）−フエニルスルホニルオキシ−ベンズイミダゾ−ル化合物 |
| JPS5910350A (ja) * | 1982-07-07 | 1984-01-19 | 井関農機株式会社 | 籾摺機のロ−タリ−セパレ−タ |
| JPS5914027A (ja) * | 1982-07-15 | 1984-01-24 | Canon Inc | 印字装置付電子機器 |
-
1982
- 1982-12-23 DE DE19823247615 patent/DE3247615A1/de not_active Withdrawn
-
1983
- 1983-12-19 HU HU834331A patent/HU192972B/hu unknown
- 1983-12-21 DE DE8383112900T patent/DE3375659D1/de not_active Expired
- 1983-12-21 EP EP83112900A patent/EP0115039B1/fr not_active Expired
- 1983-12-21 IL IL70520A patent/IL70520A/xx unknown
- 1983-12-21 GR GR73319A patent/GR79454B/el unknown
- 1983-12-21 AT AT83112900T patent/ATE32459T1/de not_active IP Right Cessation
- 1983-12-21 NZ NZ206658A patent/NZ206658A/en unknown
- 1983-12-21 KR KR1019830006059A patent/KR910000045B1/ko not_active IP Right Cessation
- 1983-12-21 PH PH30017A patent/PH21374A/en unknown
- 1983-12-21 ES ES528243A patent/ES8406448A1/es not_active Expired
- 1983-12-21 ZM ZM92/83A patent/ZM9283A1/xx unknown
- 1983-12-21 US US06/563,780 patent/US4639463A/en not_active Expired - Fee Related
- 1983-12-21 FI FI834709A patent/FI834709A/fi not_active Application Discontinuation
- 1983-12-22 CA CA000444076A patent/CA1199642A/fr not_active Expired
- 1983-12-22 NO NO834773A patent/NO834773L/no unknown
- 1983-12-22 JP JP58241121A patent/JPS59118774A/ja active Granted
- 1983-12-22 DK DK593883A patent/DK150065C/da not_active IP Right Cessation
- 1983-12-22 ZA ZA839534A patent/ZA839534B/xx unknown
- 1983-12-22 PT PT77876A patent/PT77876B/pt not_active IP Right Cessation
- 1983-12-22 AU AU22808/83A patent/AU558902B2/en not_active Ceased
- 1983-12-23 MA MA20206A patent/MA19985A1/fr unknown
-
1986
- 1986-05-02 AR AR303835A patent/AR241017A1/es active
-
1987
- 1987-09-22 MY MYPI87001851A patent/MY100900A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GR79454B (fr) | 1984-10-30 |
| DK593883D0 (da) | 1983-12-22 |
| FI834709A (fi) | 1984-06-24 |
| AU558902B2 (en) | 1987-02-12 |
| ZM9283A1 (en) | 1984-06-21 |
| DE3247615A1 (de) | 1984-07-05 |
| DK150065C (da) | 1987-10-26 |
| DK150065B (da) | 1986-12-01 |
| JPS59118774A (ja) | 1984-07-09 |
| ES528243A0 (es) | 1984-08-01 |
| EP0115039A1 (fr) | 1984-08-08 |
| DK593883A (da) | 1984-06-24 |
| ES8406448A1 (es) | 1984-08-01 |
| NZ206658A (en) | 1986-06-11 |
| PH21374A (en) | 1987-10-15 |
| US4639463A (en) | 1987-01-27 |
| EP0115039B1 (fr) | 1988-02-10 |
| AR241017A1 (es) | 1991-04-30 |
| KR840006977A (ko) | 1984-12-04 |
| ZA839534B (en) | 1984-08-29 |
| FI834709A0 (fi) | 1983-12-21 |
| MA19985A1 (fr) | 1984-07-01 |
| KR910000045B1 (ko) | 1991-01-19 |
| PT77876B (de) | 1986-04-21 |
| AR241017A2 (es) | 1991-04-30 |
| PT77876A (de) | 1984-01-01 |
| MY100900A (en) | 1991-05-16 |
| JPH0434545B2 (fr) | 1992-06-08 |
| IL70520A (en) | 1988-01-31 |
| DE3375659D1 (en) | 1988-03-17 |
| IL70520A0 (en) | 1984-03-30 |
| CA1199642A (fr) | 1986-01-21 |
| ATE32459T1 (de) | 1988-02-15 |
| HU192972B (en) | 1987-08-28 |
| AU2280883A (en) | 1984-06-28 |
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