DE2332487A1 - 2-carbalkoxy-amino-benzimidazol-5(6)phenylaether, ihre herstellung und verwendung in mitteln gegen helminthen - Google Patents
2-carbalkoxy-amino-benzimidazol-5(6)phenylaether, ihre herstellung und verwendung in mitteln gegen helminthenInfo
- Publication number
- DE2332487A1 DE2332487A1 DE2332487A DE2332487A DE2332487A1 DE 2332487 A1 DE2332487 A1 DE 2332487A1 DE 2332487 A DE2332487 A DE 2332487A DE 2332487 A DE2332487 A DE 2332487A DE 2332487 A1 DE2332487 A1 DE 2332487A1
- Authority
- DE
- Germany
- Prior art keywords
- benzimidazole
- carbon atoms
- formula
- phenoxy
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000003795 chemical substances by application Substances 0.000 title claims 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical class C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000004651 carbonic acid esters Chemical class 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 239000000460 chlorine Substances 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 239000001301 oxygen Substances 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical compound C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 230000020477 pH reduction Effects 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims description 2
- 230000007717 exclusion Effects 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- -1 alkoxy radical Chemical class 0.000 abstract description 76
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 241001465754 Metazoa Species 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 4
- 230000002496 gastric effect Effects 0.000 abstract description 2
- 244000000013 helminth Species 0.000 abstract description 2
- 241001126263 Strongylidae Species 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 abstract 1
- 230000003071 parasitic effect Effects 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 39
- 230000008018 melting Effects 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BSJFXXQHLLJOBA-UHFFFAOYSA-N 6-phenoxy-1h-benzimidazol-2-amine Chemical compound C=1C=C2NC(N)=NC2=CC=1OC1=CC=CC=C1 BSJFXXQHLLJOBA-UHFFFAOYSA-N 0.000 description 2
- YRWLZFXJFBZBEY-UHFFFAOYSA-N N-(6-butyl-1H-benzimidazol-2-yl)carbamic acid methyl ester Chemical compound CCCCC1=CC=C2N=C(NC(=O)OC)NC2=C1 YRWLZFXJFBZBEY-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 229960003439 mebendazole Drugs 0.000 description 2
- BAXLBXFAUKGCDY-UHFFFAOYSA-N mebendazole Chemical compound [CH]1C2=NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=CC=C1 BAXLBXFAUKGCDY-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 229950007337 parbendazole Drugs 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- HQZQYLGYCXEDHR-UHFFFAOYSA-N (2-methylphenyl) hydrogen carbonate Chemical compound CC1=CC=CC=C1OC(O)=O HQZQYLGYCXEDHR-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 description 1
- UGRMITBWUVWUEB-UHFFFAOYSA-N 1-$l^{1}-oxidanyl-3-methylbenzene Chemical group CC1=CC=CC([O])=C1 UGRMITBWUVWUEB-UHFFFAOYSA-N 0.000 description 1
- BHFLSZOGGDDWQM-UHFFFAOYSA-N 1h-benzimidazole;carbamic acid Chemical compound NC(O)=O.C1=CC=C2NC=NC2=C1 BHFLSZOGGDDWQM-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OJDMYVLGXHUDMW-UHFFFAOYSA-N 6-phenylsulfanyl-1h-benzimidazol-2-amine Chemical compound C1=C2NC(N)=NC2=CC=C1SC1=CC=CC=C1 OJDMYVLGXHUDMW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000893172 Chabertia Species 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000243976 Haemonchus Species 0.000 description 1
- 241000243974 Haemonchus contortus Species 0.000 description 1
- 241000920462 Heterakis 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
- 206010061217 Infestation Diseases 0.000 description 1
- KCEBZCPSLWZOGR-UHFFFAOYSA-N NC=1NC2=C(N=1)C=CC(=C2)OC1=CC=C(C=C1)OC Chemical compound NC=1NC2=C(N=1)C=CC(=C2)OC1=CC=C(C=C1)OC KCEBZCPSLWZOGR-UHFFFAOYSA-N 0.000 description 1
- 241000510960 Oesophagostomum Species 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 241000283903 Ovis aries Species 0.000 description 1
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 241000244174 Strongyloides Species 0.000 description 1
- 241000243797 Trichostrongylus Species 0.000 description 1
- 241000243796 Trichostrongylus colubriformis Species 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 239000002246 antineoplastic agent 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
- 239000006227 byproduct Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- BKNCSPZEGXUNTP-UHFFFAOYSA-N methyl (4-nitrophenyl) carbonate Chemical compound COC(=O)OC1=CC=C([N+]([O-])=O)C=C1 BKNCSPZEGXUNTP-UHFFFAOYSA-N 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000008063 pharmaceutical solvent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005303 weighing Methods 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)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2332487A DE2332487A1 (de) | 1973-06-26 | 1973-06-26 | 2-carbalkoxy-amino-benzimidazol-5(6)phenylaether, ihre herstellung und verwendung in mitteln gegen helminthen |
| ES427457A ES427457A1 (es) | 1973-06-26 | 1974-06-20 | Procedimiento para la preparacion de 2-carbalcoxi-amino- bencimidazol-5 (6)-fenileteres. |
| NL7408393A NL7408393A (enrdf_load_stackoverflow) | 1973-06-26 | 1974-06-21 | |
| IT24357/74A IT1056738B (it) | 1973-06-26 | 1974-06-24 | 2 carbalcossi amino benzimidazol 5 6 fenileteri loro prepaazione ed impiego in mezzi contro elimti |
| HUHO1684A HU168403B (enrdf_load_stackoverflow) | 1973-06-26 | 1974-06-25 | |
| YU1782/74A YU37149B (en) | 1973-06-26 | 1974-06-25 | Process for preparing 2-carbalkoxy-amino-benzimidazole-5(6)-phenylethers |
| DK341774A DK341774A (enrdf_load_stackoverflow) | 1973-06-26 | 1974-06-25 | |
| SE7408323A SE7408323L (enrdf_load_stackoverflow) | 1973-06-26 | 1974-06-25 | |
| CH871674A CH608005A5 (en) | 1973-06-26 | 1974-06-25 | Process for the preparation of novel 2-carbalkoxyamino- 5(6)-benzimidazole phenyl ethers |
| AT525574A AT342044B (de) | 1973-06-26 | 1974-06-25 | Verfahren zur herstellung von neuen 2-carbalkoxy- oder 2-carbaroxy-amino-benzimidazol-5 (6)-phenylathern und ihren salzen |
| JP49073156A JPS5753792B2 (enrdf_load_stackoverflow) | 1973-06-26 | 1974-06-26 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2332487A DE2332487A1 (de) | 1973-06-26 | 1973-06-26 | 2-carbalkoxy-amino-benzimidazol-5(6)phenylaether, ihre herstellung und verwendung in mitteln gegen helminthen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2332487A1 true DE2332487A1 (de) | 1975-01-16 |
Family
ID=5885126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2332487A Pending DE2332487A1 (de) | 1973-06-26 | 1973-06-26 | 2-carbalkoxy-amino-benzimidazol-5(6)phenylaether, ihre herstellung und verwendung in mitteln gegen helminthen |
Country Status (11)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002534452A (ja) * | 1999-01-15 | 2002-10-15 | アンジオジーン ファーマスーティカルズ リミテッド | ベンズイミダゾール血管損傷薬剤 |
-
1973
- 1973-06-26 DE DE2332487A patent/DE2332487A1/de active Pending
-
1974
- 1974-06-20 ES ES427457A patent/ES427457A1/es not_active Expired
- 1974-06-21 NL NL7408393A patent/NL7408393A/xx not_active Application Discontinuation
- 1974-06-24 IT IT24357/74A patent/IT1056738B/it active
- 1974-06-25 CH CH871674A patent/CH608005A5/xx not_active IP Right Cessation
- 1974-06-25 HU HUHO1684A patent/HU168403B/hu unknown
- 1974-06-25 YU YU1782/74A patent/YU37149B/xx unknown
- 1974-06-25 DK DK341774A patent/DK341774A/da not_active Application Discontinuation
- 1974-06-25 SE SE7408323A patent/SE7408323L/xx not_active Application Discontinuation
- 1974-06-25 AT AT525574A patent/AT342044B/de not_active IP Right Cessation
- 1974-06-26 JP JP49073156A patent/JPS5753792B2/ja not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002534452A (ja) * | 1999-01-15 | 2002-10-15 | アンジオジーン ファーマスーティカルズ リミテッド | ベンズイミダゾール血管損傷薬剤 |
| JP5026636B2 (ja) * | 1999-01-15 | 2012-09-12 | アンジオジーン ファーマスーティカルズ リミテッド | ベンズイミダゾール血管損傷薬剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA525574A (de) | 1977-07-15 |
| IT1056738B (it) | 1982-02-20 |
| JPS5753792B2 (enrdf_load_stackoverflow) | 1982-11-15 |
| ES427457A1 (es) | 1976-07-16 |
| YU37149B (en) | 1984-08-31 |
| HU168403B (enrdf_load_stackoverflow) | 1976-04-28 |
| SE7408323L (enrdf_load_stackoverflow) | 1974-12-27 |
| JPS5040566A (enrdf_load_stackoverflow) | 1975-04-14 |
| AT342044B (de) | 1978-03-10 |
| YU178274A (en) | 1982-06-18 |
| DK341774A (enrdf_load_stackoverflow) | 1975-03-17 |
| NL7408393A (enrdf_load_stackoverflow) | 1974-12-30 |
| CH608005A5 (en) | 1978-12-15 |
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