SU691089A3 - Способ получени карбонилзамещенных 1-сульфонилбензимидазолов - Google Patents
Способ получени карбонилзамещенных 1-сульфонилбензимидазоловInfo
- Publication number
- SU691089A3 SU691089A3 SU762390305A SU2390305A SU691089A3 SU 691089 A3 SU691089 A3 SU 691089A3 SU 762390305 A SU762390305 A SU 762390305A SU 2390305 A SU2390305 A SU 2390305A SU 691089 A3 SU691089 A3 SU 691089A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- amino
- product
- mixture
- mol
- solution
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 35
- 239000000047 product Substances 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 229940086542 triethylamine Drugs 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- -1 benzimidazole compound Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YOROYHPRNGLSAT-UHFFFAOYSA-N (4-amino-3-nitrophenyl)methanol Chemical compound NC1=CC=C(CO)C=C1[N+]([O-])=O YOROYHPRNGLSAT-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- RXCOGDYOZQGGMK-UHFFFAOYSA-N (3,4-diaminophenyl)-phenylmethanone Chemical compound C1=C(N)C(N)=CC=C1C(=O)C1=CC=CC=C1 RXCOGDYOZQGGMK-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- HMVJXTUUQJUYJI-UHFFFAOYSA-N (3,4-diaminophenyl)methanol Chemical compound NC1=CC=C(CO)C=C1N HMVJXTUUQJUYJI-UHFFFAOYSA-N 0.000 description 1
- NGOOFAMQPUEDJM-UHFFFAOYSA-N (4-amino-3-nitrophenyl)-phenylmethanone Chemical compound C1=C([N+]([O-])=O)C(N)=CC=C1C(=O)C1=CC=CC=C1 NGOOFAMQPUEDJM-UHFFFAOYSA-N 0.000 description 1
- RBKHNGHPZZZJCI-UHFFFAOYSA-N (4-aminophenyl)-phenylmethanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 RBKHNGHPZZZJCI-UHFFFAOYSA-N 0.000 description 1
- UYFMRVDIXXOWLR-UHFFFAOYSA-N 1-(1h-benzimidazol-2-yl)ethanone Chemical compound C1=CC=C2NC(C(=O)C)=NC2=C1 UYFMRVDIXXOWLR-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- GPMHHSJZGVOEFS-UHFFFAOYSA-N 2-Amino-5-benzoylbenzimidazole Chemical compound C1=C2NC(N)=NC2=CC=C1C(=O)C1=CC=CC=C1 GPMHHSJZGVOEFS-UHFFFAOYSA-N 0.000 description 1
- CGVCBANYMPJILL-UHFFFAOYSA-N 3h-benzimidazol-5-yl(phenyl)methanone Chemical compound C=1C=C2N=CNC2=CC=1C(=O)C1=CC=CC=C1 CGVCBANYMPJILL-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GETROXFXSFTXOI-UHFFFAOYSA-N C[ClH]S([ClH]C)(=O)=O Chemical compound C[ClH]S([ClH]C)(=O)=O GETROXFXSFTXOI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 208000002286 Susac Syndrome Diseases 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RLDQYSHDFVSAPL-UHFFFAOYSA-L calcium;dithiocyanate Chemical compound [Ca+2].[S-]C#N.[S-]C#N RLDQYSHDFVSAPL-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- MRYGLSXFXNZSSV-UHFFFAOYSA-N dimethylsulfamic acid;hydrochloride Chemical compound Cl.CN(C)S(O)(=O)=O MRYGLSXFXNZSSV-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- ZCHQDHMYPQXPQL-UHFFFAOYSA-N ethyl 2-amino-3h-benzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=C(N)NC2=C1 ZCHQDHMYPQXPQL-UHFFFAOYSA-N 0.000 description 1
- HUOIDCCHUGUZQS-UHFFFAOYSA-N ethyl 3h-benzimidazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=CNC2=C1 HUOIDCCHUGUZQS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- OBEXUAPBTUTPDV-UHFFFAOYSA-N n-(4-benzoylphenyl)acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)C1=CC=CC=C1 OBEXUAPBTUTPDV-UHFFFAOYSA-N 0.000 description 1
- RBMBUFMMNAPTJP-UHFFFAOYSA-N n-(dimethylamino)sulfamoyl chloride Chemical compound CN(C)NS(Cl)(=O)=O RBMBUFMMNAPTJP-UHFFFAOYSA-N 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60841575A | 1975-08-28 | 1975-08-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU691089A3 true SU691089A3 (ru) | 1979-10-05 |
Family
ID=24436401
Family Applications (9)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762390305A SU691089A3 (ru) | 1975-08-28 | 1976-08-26 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU772524545A SU730300A3 (ru) | 1975-08-28 | 1977-09-27 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU772525453A SU685151A3 (ru) | 1975-08-28 | 1977-09-28 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU772527447A SU679140A3 (ru) | 1975-08-28 | 1977-09-29 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU772526201A SU884570A3 (ru) | 1975-08-28 | 1977-09-29 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU782647712A SU730301A3 (ru) | 1975-08-28 | 1978-08-16 | Способ получени замещенных 1-сульфонилбензимидазолов |
| SU782654600A SU727142A3 (ru) | 1975-08-28 | 1978-08-31 | Способ получени замещенных 1-сульфонилбензимидазолов |
| SU782676704A SU919593A3 (ru) | 1975-08-28 | 1978-10-23 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU782676705A SU784767A3 (ru) | 1975-08-28 | 1978-10-24 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
Family Applications After (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU772524545A SU730300A3 (ru) | 1975-08-28 | 1977-09-27 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU772525453A SU685151A3 (ru) | 1975-08-28 | 1977-09-28 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU772527447A SU679140A3 (ru) | 1975-08-28 | 1977-09-29 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU772526201A SU884570A3 (ru) | 1975-08-28 | 1977-09-29 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU782647712A SU730301A3 (ru) | 1975-08-28 | 1978-08-16 | Способ получени замещенных 1-сульфонилбензимидазолов |
| SU782654600A SU727142A3 (ru) | 1975-08-28 | 1978-08-31 | Способ получени замещенных 1-сульфонилбензимидазолов |
| SU782676704A SU919593A3 (ru) | 1975-08-28 | 1978-10-23 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
| SU782676705A SU784767A3 (ru) | 1975-08-28 | 1978-10-24 | Способ получени карбонилзамещенных 1-сульфонилбензимидазолов |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4118742A (enExample) |
| JP (4) | JPS5633392B2 (enExample) |
| AR (4) | AR219284A1 (enExample) |
| AT (1) | AT360005B (enExample) |
| AU (1) | AU502756B2 (enExample) |
| BE (1) | BE845641A (enExample) |
| BG (1) | BG27548A3 (enExample) |
| CA (1) | CA1064501A (enExample) |
| CH (8) | CH626612A5 (enExample) |
| DD (1) | DD126518A5 (enExample) |
| DE (1) | DE2638551A1 (enExample) |
| DK (1) | DK154764C (enExample) |
| ES (5) | ES451018A1 (enExample) |
| FR (1) | FR2321883A1 (enExample) |
| GB (1) | GB1562812A (enExample) |
| GR (1) | GR61627B (enExample) |
| HU (1) | HU173988B (enExample) |
| IE (1) | IE43531B1 (enExample) |
| IL (1) | IL50292A (enExample) |
| MX (1) | MX3654E (enExample) |
| NL (1) | NL7609414A (enExample) |
| NZ (1) | NZ181789A (enExample) |
| PL (4) | PL115117B1 (enExample) |
| PT (1) | PT65486B (enExample) |
| RO (5) | RO78125A (enExample) |
| SU (9) | SU691089A3 (enExample) |
| YU (2) | YU203476A (enExample) |
| ZA (1) | ZA765142B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4191832A (en) * | 1979-03-12 | 1980-03-04 | Eli Lilly And Company | Separation of syn and anti oximes of 1-sulfonyl-2-aminobenzimidazoles |
| CA1178889A (en) * | 1980-08-28 | 1984-12-04 | Kenneth S. Su | Intranasal formulation |
| FR2521141A1 (fr) * | 1982-02-09 | 1983-08-12 | Rhone Poulenc Agrochimie | Nouveaux derives du cyano-2 benzimidazole, leur preparation et leur utilisation comme fongicides |
| US4420479A (en) * | 1982-04-08 | 1983-12-13 | Eli Lilly And Company | Olefinic benzimidazoles, formulations, and antiviral methods |
| US4463181A (en) * | 1982-04-08 | 1984-07-31 | Eli Lilly And Company | Process for removing sulfonyl groups from benzimidazole isomers |
| IL68297A (en) * | 1982-04-08 | 1986-09-30 | Lilly Co Eli | Process for removing 1-sulfonyl groups from 2-amino-5(6)-substituted benzimidazoles |
| US4434288A (en) | 1982-04-08 | 1984-02-28 | Eli Lilly And Company | Preparation of substituted 1-thiazinyl or 1-thiazolyl-2-aminobenzimidazoles |
| US4483986A (en) * | 1982-05-03 | 1984-11-20 | Eli Lilly And Company | 4-Nitrobenzophenone compounds |
| US4645861A (en) * | 1982-05-03 | 1987-02-24 | Eli Lilly And Company | 3-sulfonylamino-4-amino phenyl acyl derivatives |
| US4629811A (en) * | 1982-05-03 | 1986-12-16 | Eli Lilly And Company | 3-sulfonylamino-4-aminobenzophenone derivatives |
| US4492708A (en) * | 1982-09-27 | 1985-01-08 | Eli Lilly And Company | Antiviral benzimidazoles |
| US4501921A (en) * | 1982-11-18 | 1985-02-26 | Eli Lilly And Company | Synthesis of alkylidene intermediates |
| US4435418A (en) * | 1982-12-13 | 1984-03-06 | Smithkline Beckman Corporation | 5-Phenylethenylbenzimidazoles |
| JPS62196293U (enExample) * | 1986-06-03 | 1987-12-14 | ||
| CA1339133C (en) * | 1987-03-13 | 1997-07-29 | Rikuo Nasu | Imidazole compounds and biocidal composition comprising the same for controlling harmful organisms |
| JPS6410894A (en) * | 1987-06-30 | 1989-01-13 | Nitto Koji Kk | Burying propulsion correcting method and device for propulsive pipe for burying hume pipe |
| US5545653A (en) * | 1995-06-07 | 1996-08-13 | Eli Lilly And Company | Anti-viral compounds |
| EP1001767A4 (en) * | 1997-06-04 | 2001-07-04 | Lilly Co Eli | ANTIVIRAL CONNECTIONS |
| US6358971B1 (en) | 1998-05-20 | 2002-03-19 | Eli Lilly And Company | Anti-viral compounds |
| US7470723B2 (en) * | 2003-03-05 | 2008-12-30 | Celgene Corporation | Diphenylethylene compounds and uses thereof |
| US8287843B2 (en) * | 2003-06-23 | 2012-10-16 | Colgate-Palmolive Company | Antiplaque oral care compositions |
| SG144809A1 (en) * | 2007-01-11 | 2008-08-28 | Millipore U K Ltd | Benzimidazole compounds and their use as chromatographic ligands |
| TWI811428B (zh) | 2018-08-21 | 2023-08-11 | 日商杏林製藥股份有限公司 | 雙環雜芳香環衍生物 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1170737A (en) * | 1964-05-27 | 1969-11-12 | Fisons Pest Control Ltd | Substituted Benzimadazoles and their use as Acaricides |
| US3682952A (en) * | 1964-08-04 | 1972-08-08 | Smith Kline French Lab | 5(6)-n-butyl-2-carbomethoxy-benzimidazole |
| DE2034643A1 (de) * | 1970-03-06 | 1971-09-16 | Deutsche Akademie der Wissenschaften zu Berlin, χ 1199 Berlin | Verfahren zur Herstellung von virustatisch wirksamen p-N-Methylnitrosaminophenyl-Verbindungen |
| BE795099A (fr) * | 1972-02-09 | 1973-08-07 | Bayer Ag | Nouvelles 1-acyl-3-aminosulfonyl-2-imino-benzimidazolines, leur procede de preparation et leur application comme fongicides |
| BE795098A (fr) * | 1972-02-09 | 1973-08-07 | Bayer Ag | Nouveaux 1-aminosulfonyl-2-amino-benzimidazoles, leur procede de preparation et leur application comme fongicides |
-
1976
- 1976-08-17 GR GR51488A patent/GR61627B/el unknown
- 1976-08-17 NZ NZ181789A patent/NZ181789A/xx unknown
- 1976-08-17 MX MX763667U patent/MX3654E/es unknown
- 1976-08-17 PT PT65486A patent/PT65486B/pt unknown
- 1976-08-18 HU HU76EI694A patent/HU173988B/hu unknown
- 1976-08-18 IL IL50292A patent/IL50292A/xx unknown
- 1976-08-19 CA CA259,487A patent/CA1064501A/en not_active Expired
- 1976-08-19 AR AR264377A patent/AR219284A1/es active
- 1976-08-19 AU AU16982/76A patent/AU502756B2/en not_active Expired
- 1976-08-19 YU YU02034/76A patent/YU203476A/xx unknown
- 1976-08-24 IE IE1884/76A patent/IE43531B1/en not_active IP Right Cessation
- 1976-08-24 GB GB35153/76A patent/GB1562812A/en not_active Expired
- 1976-08-24 NL NL7609414A patent/NL7609414A/xx not_active Application Discontinuation
- 1976-08-25 RO RO7698737A patent/RO78125A/ro unknown
- 1976-08-25 RO RO7698735A patent/RO78123A/ro unknown
- 1976-08-25 JP JP10219076A patent/JPS5633392B2/ja not_active Expired
- 1976-08-25 RO RO7698734A patent/RO78122A/ro unknown
- 1976-08-25 RO RO7698736A patent/RO78124A/ro unknown
- 1976-08-25 RO RO7687359A patent/RO72313A/ro unknown
- 1976-08-26 SU SU762390305A patent/SU691089A3/ru active
- 1976-08-26 PL PL1976209626A patent/PL115117B1/pl unknown
- 1976-08-26 ES ES451018A patent/ES451018A1/es not_active Expired
- 1976-08-26 PL PL1976192018A patent/PL106947B1/pl unknown
- 1976-08-26 BG BG034083A patent/BG27548A3/xx unknown
- 1976-08-26 PL PL1976218028A patent/PL112910B1/pl unknown
- 1976-08-26 DK DK386076A patent/DK154764C/da not_active IP Right Cessation
- 1976-08-26 CH CH1085476A patent/CH626612A5/de not_active IP Right Cessation
- 1976-08-26 PL PL1976209627A patent/PL110145B1/pl unknown
- 1976-08-26 DE DE19762638551 patent/DE2638551A1/de active Granted
- 1976-08-26 AT AT636376A patent/AT360005B/de not_active IP Right Cessation
- 1976-08-27 ZA ZA00765142A patent/ZA765142B/xx unknown
- 1976-08-27 DD DD194505A patent/DD126518A5/xx unknown
- 1976-08-27 BE BE1007586A patent/BE845641A/xx not_active IP Right Cessation
- 1976-08-27 FR FR7626026A patent/FR2321883A1/fr active Granted
- 1976-12-15 US US05/750,991 patent/US4118742A/en not_active Expired - Lifetime
-
1977
- 1977-02-14 YU YU00390/77A patent/YU39077A/xx unknown
- 1977-08-16 ES ES461644A patent/ES461644A1/es not_active Expired
- 1977-08-16 ES ES461643A patent/ES461643A1/es not_active Expired
- 1977-08-16 AR AR268810A patent/AR221037A1/es active
- 1977-08-16 ES ES461642A patent/ES461642A1/es not_active Expired
- 1977-08-16 ES ES461641A patent/ES461641A1/es not_active Expired
- 1977-09-27 SU SU772524545A patent/SU730300A3/ru active
- 1977-09-28 SU SU772525453A patent/SU685151A3/ru active
- 1977-09-29 SU SU772527447A patent/SU679140A3/ru active
- 1977-09-29 SU SU772526201A patent/SU884570A3/ru active
-
1978
- 1978-06-15 AR AR272626A patent/AR220344A1/es active
- 1978-06-15 AR AR272625A patent/AR221701A1/es active
- 1978-08-16 SU SU782647712A patent/SU730301A3/ru active
- 1978-08-31 SU SU782654600A patent/SU727142A3/ru active
- 1978-10-23 SU SU782676704A patent/SU919593A3/ru active
- 1978-10-24 SU SU782676705A patent/SU784767A3/ru active
-
1980
- 1980-06-30 CH CH503080A patent/CH627753A5/de not_active IP Right Cessation
- 1980-06-30 CH CH502880A patent/CH627455A5/de not_active IP Right Cessation
- 1980-06-30 CH CH502780A patent/CH627748A5/de not_active IP Right Cessation
- 1980-06-30 CH CH502980A patent/CH628035A5/de not_active IP Right Cessation
- 1980-07-03 CH CH513781A patent/CH630917A5/de not_active IP Right Cessation
- 1980-07-03 CH CH513681A patent/CH630376A5/de not_active IP Right Cessation
- 1980-11-26 JP JP55167907A patent/JPS591712B2/ja not_active Expired
- 1980-11-26 JP JP55167906A patent/JPS5823876B2/ja not_active Expired
- 1980-11-26 JP JP55167905A patent/JPS57112389A/ja active Pending
-
1981
- 1981-08-10 CH CH513881A patent/CH631447A5/de not_active IP Right Cessation
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