IL124969A - תולדות בנזאימידזול, תהליכים להכנתן ותכשירי רוקחות המכילים אותן - Google Patents
תולדות בנזאימידזול, תהליכים להכנתן ותכשירי רוקחות המכילים אותןInfo
- Publication number
- IL124969A IL124969A IL12496996A IL12496996A IL124969A IL 124969 A IL124969 A IL 124969A IL 12496996 A IL12496996 A IL 12496996A IL 12496996 A IL12496996 A IL 12496996A IL 124969 A IL124969 A IL 124969A
- Authority
- IL
- Israel
- Prior art keywords
- group
- lower alkyl
- alkyl group
- compound
- benzimidazole
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 5
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title abstract description 23
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 17
- 238000000034 method Methods 0.000 title description 7
- 239000008194 pharmaceutical composition Substances 0.000 title description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 164
- 125000003118 aryl group Chemical group 0.000 claims abstract description 43
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 34
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 31
- 125000005843 halogen group Chemical group 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000001424 substituent group Chemical group 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 125000003277 amino group Chemical group 0.000 claims abstract description 15
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 11
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract description 6
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims abstract description 6
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 6
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 5
- 125000002944 cyanoaryl group Chemical group 0.000 claims abstract description 5
- 125000003106 haloaryl group Chemical group 0.000 claims abstract description 5
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims abstract description 4
- 210000004369 blood Anatomy 0.000 claims abstract description 4
- 239000008280 blood Substances 0.000 claims abstract description 4
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 4
- 101100189582 Dictyostelium discoideum pdeD gene Proteins 0.000 claims abstract description 3
- 101150098694 PDE5A gene Proteins 0.000 claims abstract description 3
- 102100029175 cGMP-specific 3',5'-cyclic phosphodiesterase Human genes 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 125000005493 quinolyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- JYZIHLWOWKMNNX-UHFFFAOYSA-N benzimidazole Chemical compound C1=C[CH]C2=NC=NC2=C1 JYZIHLWOWKMNNX-UHFFFAOYSA-N 0.000 claims 3
- 241000282320 Panthera leo Species 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000000881 depressing effect Effects 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 516
- -1 benzimidazole compound Chemical class 0.000 description 450
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 273
- 230000015572 biosynthetic process Effects 0.000 description 258
- 238000003786 synthesis reaction Methods 0.000 description 258
- 238000005160 1H NMR spectroscopy Methods 0.000 description 229
- 239000000203 mixture Substances 0.000 description 215
- 239000000243 solution Substances 0.000 description 187
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 180
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 178
- 238000004519 manufacturing process Methods 0.000 description 155
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 141
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 133
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 127
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 122
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 115
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 110
- 230000002829 reductive effect Effects 0.000 description 110
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 108
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 102
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 102
- 101150041968 CDC13 gene Proteins 0.000 description 98
- 238000006243 chemical reaction Methods 0.000 description 95
- 239000013078 crystal Substances 0.000 description 84
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- 238000001914 filtration Methods 0.000 description 72
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 68
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 67
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 66
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 66
- 239000000126 substance Substances 0.000 description 60
- 239000012044 organic layer Substances 0.000 description 58
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 50
- 239000007864 aqueous solution Substances 0.000 description 49
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 48
- 238000010898 silica gel chromatography Methods 0.000 description 48
- 239000002904 solvent Substances 0.000 description 46
- 239000003480 eluent Substances 0.000 description 45
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 39
- VXBLDUOHSHPNKR-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-2-methylbenzimidazole-5-carboxylic acid Chemical compound CC1=NC2=CC=C(C(O)=O)C=C2N1CC1=CC=CC=C1Cl VXBLDUOHSHPNKR-UHFFFAOYSA-N 0.000 description 38
- 235000017557 sodium bicarbonate Nutrition 0.000 description 33
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 33
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical compound NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- 239000000706 filtrate Substances 0.000 description 27
- 239000011343 solid material Substances 0.000 description 24
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 21
- CBDHQIOQTZNJKO-UHFFFAOYSA-N ethyl 3-acetamido-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(C)=O)=C1 CBDHQIOQTZNJKO-UHFFFAOYSA-N 0.000 description 21
- 239000011736 potassium bicarbonate Substances 0.000 description 21
- 235000015497 potassium bicarbonate Nutrition 0.000 description 21
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 21
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 21
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 21
- OVIZSQRQYWEGON-UHFFFAOYSA-N butane-1-sulfonamide Chemical compound CCCCS(N)(=O)=O OVIZSQRQYWEGON-UHFFFAOYSA-N 0.000 description 20
- 150000002148 esters Chemical class 0.000 description 20
- 239000011259 mixed solution Substances 0.000 description 20
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 229920006395 saturated elastomer Polymers 0.000 description 20
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 19
- 239000010410 layer Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 235000011121 sodium hydroxide Nutrition 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 229910052739 hydrogen Inorganic materials 0.000 description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
- 239000012298 atmosphere Substances 0.000 description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- WZVJKXJRWSRGNA-UHFFFAOYSA-N 3-[(2,4-dichlorophenyl)methyl]-2-methylbenzimidazole-5-carboxylic acid Chemical compound CC1=NC2=CC=C(C(O)=O)C=C2N1CC1=CC=C(Cl)C=C1Cl WZVJKXJRWSRGNA-UHFFFAOYSA-N 0.000 description 11
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 239000012046 mixed solvent Substances 0.000 description 11
- LBATZZNFAPQUDG-UHFFFAOYSA-N n-(benzenesulfonyl)-3-[(2-chlorophenyl)methyl]-2-methylbenzimidazole-5-carboxamide Chemical compound CC1=NC2=CC=C(C(=O)NS(=O)(=O)C=3C=CC=CC=3)C=C2N1CC1=CC=CC=C1Cl LBATZZNFAPQUDG-UHFFFAOYSA-N 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- 229910000104 sodium hydride Inorganic materials 0.000 description 11
- ACRMYCWODJZYOX-UHFFFAOYSA-N 4-amino-n-(benzenesulfonyl)-3-[(4-phenylphenyl)methylamino]benzamide Chemical compound NC1=CC=C(C(=O)NS(=O)(=O)C=2C=CC=CC=2)C=C1NCC(C=C1)=CC=C1C1=CC=CC=C1 ACRMYCWODJZYOX-UHFFFAOYSA-N 0.000 description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 10
- 208000035475 disorder Diseases 0.000 description 10
- HWPMTUWWESZFAI-UHFFFAOYSA-N ethyl 3-(butanoylamino)-4-nitrobenzoate Chemical compound CCCC(=O)NC1=CC(C(=O)OCC)=CC=C1[N+]([O-])=O HWPMTUWWESZFAI-UHFFFAOYSA-N 0.000 description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 description 10
- 229910052763 palladium Inorganic materials 0.000 description 10
- 229910052697 platinum Inorganic materials 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 235000011181 potassium carbonates Nutrition 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 229910052707 ruthenium Inorganic materials 0.000 description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- 229910052723 transition metal Inorganic materials 0.000 description 10
- 150000003624 transition metals Chemical class 0.000 description 10
- OWIIKUBEZQOWFN-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-2-methylbenzimidazole-5-carboxylic acid Chemical compound CC1=NC2=CC(C(O)=O)=CC=C2N1CC1=CC=CC=C1Cl OWIIKUBEZQOWFN-UHFFFAOYSA-N 0.000 description 9
- NZZHCBSIEDNIBP-UHFFFAOYSA-N 2-ethyl-3-[(4-phenylphenyl)methyl]benzimidazole-5-carboxylic acid Chemical compound CCC1=NC2=CC=C(C(O)=O)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1 NZZHCBSIEDNIBP-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 229910052759 nickel Inorganic materials 0.000 description 9
- 235000011118 potassium hydroxide Nutrition 0.000 description 9
- IWJWJRVLWQNTLK-UHFFFAOYSA-N 2-methyl-3-[(4-nitrophenyl)methyl]-n-(pyridin-2-ylmethyl)benzimidazole-5-carboxamide Chemical compound CC1=NC2=CC=C(C(=O)NCC=3N=CC=CC=3)C=C2N1CC1=CC=C([N+]([O-])=O)C=C1 IWJWJRVLWQNTLK-UHFFFAOYSA-N 0.000 description 8
- STCDYPPZLYRJJV-UHFFFAOYSA-N 2-methyl-n-(pyridin-2-ylmethyl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C2NC(C)=NC2=CC=C1C(=O)NCC1=CC=CC=N1 STCDYPPZLYRJJV-UHFFFAOYSA-N 0.000 description 8
- PEYYHLQYLVINDR-UHFFFAOYSA-N 3-[(2,4-dichlorophenyl)methyl]-2-methylbenzimidazole-4-carboxylic acid Chemical compound CC1=NC2=CC=CC(C(O)=O)=C2N1CC1=CC=C(Cl)C=C1Cl PEYYHLQYLVINDR-UHFFFAOYSA-N 0.000 description 8
- 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 8
- SMUPCXIVIMRZES-UHFFFAOYSA-N 4-acetamido-3-amino-n-(benzenesulfonyl)benzamide Chemical compound C1=C(N)C(NC(=O)C)=CC=C1C(=O)NS(=O)(=O)C1=CC=CC=C1 SMUPCXIVIMRZES-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- 125000005907 alkyl ester group Chemical group 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- MERQGHQOZBNNEZ-UHFFFAOYSA-N ethyl 2-methyl-3-[(2-nitrophenyl)methyl]benzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2N=C(C)N1CC1=CC=CC=C1[N+]([O-])=O MERQGHQOZBNNEZ-UHFFFAOYSA-N 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- USJSQUNOKHIBLT-UHFFFAOYSA-N n-(benzenesulfonyl)-3-[(4-phenylphenyl)methyl]-2-propylbenzimidazole-5-carboxamide;potassium Chemical compound [K].CCCC1=NC2=CC=C(C(=O)NS(=O)(=O)C=3C=CC=CC=3)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1 USJSQUNOKHIBLT-UHFFFAOYSA-N 0.000 description 8
- FITCYRGVVTUPAD-UHFFFAOYSA-N n-(benzenesulfonyl)-3-[(4-phenylphenyl)methyl]-2-sulfanylidene-1h-benzimidazole-5-carboxamide Chemical compound SC1=NC2=CC=C(C(=O)NS(=O)(=O)C=3C=CC=CC=3)C=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1 FITCYRGVVTUPAD-UHFFFAOYSA-N 0.000 description 8
- SSXYUKNCNOYRFP-UHFFFAOYSA-N n-butylsulfonyl-1-[(2,4-dichlorophenyl)methyl]-2-methylbenzimidazole-4-carboxamide Chemical compound CC1=NC=2C(C(=O)NS(=O)(=O)CCCC)=CC=CC=2N1CC1=CC=C(Cl)C=C1Cl SSXYUKNCNOYRFP-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- SHTLKENIEWKWAF-UHFFFAOYSA-N 1-[(2,4-dichlorophenyl)methyl]-2-methylbenzimidazole-4-carboxylic acid Chemical compound CC1=NC2=C(C(O)=O)C=CC=C2N1CC1=CC=C(Cl)C=C1Cl SHTLKENIEWKWAF-UHFFFAOYSA-N 0.000 description 7
- WSQPDIQKGZCEQF-UHFFFAOYSA-N 1-[(2,4-dichlorophenyl)methyl]-2-methylbenzimidazole-5-carboxylic acid Chemical compound CC1=NC2=CC(C(O)=O)=CC=C2N1CC1=CC=C(Cl)C=C1Cl WSQPDIQKGZCEQF-UHFFFAOYSA-N 0.000 description 7
- SMEDXCVKEFQQLW-UHFFFAOYSA-N 2-benzyl-1-[(2,4-dichlorophenyl)methyl]benzimidazole-5-carboxylic acid Chemical compound C=1C=CC=CC=1CC1=NC2=CC(C(=O)O)=CC=C2N1CC1=CC=C(Cl)C=C1Cl SMEDXCVKEFQQLW-UHFFFAOYSA-N 0.000 description 7
- MKVRXNZPJRSQJI-UHFFFAOYSA-N 2-benzyl-1-[(2-chlorophenyl)methyl]benzimidazole-5-carboxylic acid Chemical compound C=1C=CC=CC=1CC1=NC2=CC(C(=O)O)=CC=C2N1CC1=CC=CC=C1Cl MKVRXNZPJRSQJI-UHFFFAOYSA-N 0.000 description 7
- VVGSNGXMGLBNDR-UHFFFAOYSA-N 2-benzyl-3-[(2,4-dichlorophenyl)methyl]benzimidazole-5-carboxylic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1CN1C2=CC(C(=O)O)=CC=C2N=C1CC1=CC=CC=C1 VVGSNGXMGLBNDR-UHFFFAOYSA-N 0.000 description 7
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- DEKSQJCUMFLDSE-UHFFFAOYSA-N 2-ethyl-3-[[4-[(4-fluorophenyl)methoxy]phenyl]methyl]benzimidazole-5-carboxylic acid Chemical compound CCC1=NC2=CC=C(C(O)=O)C=C2N1CC(C=C1)=CC=C1OCC1=CC=C(F)C=C1 DEKSQJCUMFLDSE-UHFFFAOYSA-N 0.000 description 7
- OXQKLMRTGRDXEY-UHFFFAOYSA-N 2-methyl-1-[(4-nitrophenyl)methyl]-n-(pyridin-2-ylmethyl)benzimidazole-5-carboxamide Chemical compound CC1=NC2=CC(C(=O)NCC=3N=CC=CC=3)=CC=C2N1CC1=CC=C([N+]([O-])=O)C=C1 OXQKLMRTGRDXEY-UHFFFAOYSA-N 0.000 description 7
- DZZFOQAEJHRWCF-UHFFFAOYSA-N 2-methyl-3-(naphthalen-2-ylmethyl)benzimidazole-5-carboxylic acid Chemical compound C1=CC=CC2=CC(CN3C4=CC(=CC=C4N=C3C)C(O)=O)=CC=C21 DZZFOQAEJHRWCF-UHFFFAOYSA-N 0.000 description 7
- GIQCZVXVGZVOGK-UHFFFAOYSA-N 2-methyl-3-[(2-methylphenyl)methyl]benzimidazole-5-carboxylic acid Chemical compound CC1=NC2=CC=C(C(O)=O)C=C2N1CC1=CC=CC=C1C GIQCZVXVGZVOGK-UHFFFAOYSA-N 0.000 description 7
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- AOIQCFKRKVRAML-UHFFFAOYSA-N ethyl 1-[(2-chlorophenyl)methyl]-2-propylbenzimidazole-5-carboxylate Chemical compound CCCC1=NC2=CC(C(=O)OCC)=CC=C2N1CC1=CC=CC=C1Cl AOIQCFKRKVRAML-UHFFFAOYSA-N 0.000 description 1
- HSPRRDJVEWBNLA-UHFFFAOYSA-N ethyl 1-[(4-phenylphenyl)methyl]-2-(trifluoromethyl)benzimidazole-5-carboxylate Chemical compound FC(F)(F)C1=NC2=CC(C(=O)OCC)=CC=C2N1CC(C=C1)=CC=C1C1=CC=CC=C1 HSPRRDJVEWBNLA-UHFFFAOYSA-N 0.000 description 1
- DHHPOFBDBWILJD-UHFFFAOYSA-N ethyl 2-butanoyl-3-methylbenzimidazole-5-carboxylate Chemical compound C1=C(C(=O)OCC)C=C2N(C)C(C(=O)CCC)=NC2=C1 DHHPOFBDBWILJD-UHFFFAOYSA-N 0.000 description 1
- JBSBCXOFXBKFLE-UHFFFAOYSA-N ethyl 2-butyl-1-[(2-chlorophenyl)methyl]benzimidazole-5-carboxylate Chemical compound CCCCC1=NC2=CC(C(=O)OCC)=CC=C2N1CC1=CC=CC=C1Cl JBSBCXOFXBKFLE-UHFFFAOYSA-N 0.000 description 1
- BNUNHYBUAGBQNQ-UHFFFAOYSA-N ethyl 2-butyl-3-[(2,4-dichlorophenyl)methyl]benzimidazole-5-carboxylate Chemical compound CCCCC1=NC2=CC=C(C(=O)OCC)C=C2N1CC1=CC=C(Cl)C=C1Cl BNUNHYBUAGBQNQ-UHFFFAOYSA-N 0.000 description 1
- SWMNIHOCVWTZOW-UHFFFAOYSA-N ethyl 2-butyl-3-[(2-chlorophenyl)methyl]benzimidazole-4-carboxylate Chemical compound CCCCC1=NC2=CC=CC(C(=O)OCC)=C2N1CC1=CC=CC=C1Cl SWMNIHOCVWTZOW-UHFFFAOYSA-N 0.000 description 1
- VFHGGXLXVCGUHU-UHFFFAOYSA-N ethyl 2-butyl-3-[(2-chlorophenyl)methyl]benzimidazole-5-carboxylate Chemical compound CCCCC1=NC2=CC=C(C(=O)OCC)C=C2N1CC1=CC=CC=C1Cl VFHGGXLXVCGUHU-UHFFFAOYSA-N 0.000 description 1
- LDPIBXSATNAAKO-UHFFFAOYSA-N ethyl 2-butyl-3-[(2-fluorophenyl)methyl]benzimidazole-5-carboxylate Chemical compound CCCCC1=NC2=CC=C(C(=O)OCC)C=C2N1CC1=CC=CC=C1F LDPIBXSATNAAKO-UHFFFAOYSA-N 0.000 description 1
- KDSAVLKIILGCGL-UHFFFAOYSA-N ethyl 2-butyl-3-[(4-methoxycarbonylphenyl)methyl]benzimidazole-5-carboxylate Chemical compound CCCCC1=NC2=CC=C(C(=O)OCC)C=C2N1CC1=CC=C(C(=O)OC)C=C1 KDSAVLKIILGCGL-UHFFFAOYSA-N 0.000 description 1
- ZABMVIXLNVLRKD-UHFFFAOYSA-N ethyl 2-ethyl-3-[(4-phenylphenyl)methyl]benzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2N=C(CC)N1CC(C=C1)=CC=C1C1=CC=CC=C1 ZABMVIXLNVLRKD-UHFFFAOYSA-N 0.000 description 1
- IXPMDUYNZLMKEW-UHFFFAOYSA-N ethyl 2-methyl-3-(quinolin-2-ylmethyl)benzimidazole-5-carboxylate Chemical compound C1=CC=CC2=NC(CN3C(C)=NC4=CC=C(C=C43)C(=O)OCC)=CC=C21 IXPMDUYNZLMKEW-UHFFFAOYSA-N 0.000 description 1
- OXNSWCMRHCSKTI-UHFFFAOYSA-N ethyl 2-methyl-3-[(2-phenylphenyl)methyl]benzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2N=C(C)N1CC1=CC=CC=C1C1=CC=CC=C1 OXNSWCMRHCSKTI-UHFFFAOYSA-N 0.000 description 1
- PMLFVJNWXBNZJW-UHFFFAOYSA-N ethyl 2-methyl-3-[(4-nitrophenyl)methyl]benzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2N=C(C)N1CC1=CC=C([N+]([O-])=O)C=C1 PMLFVJNWXBNZJW-UHFFFAOYSA-N 0.000 description 1
- FGQYSIFRJGBMQS-UHFFFAOYSA-N ethyl 2-methyl-3-[(4-phenoxyphenyl)methyl]benzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2N=C(C)N1CC(C=C1)=CC=C1OC1=CC=CC=C1 FGQYSIFRJGBMQS-UHFFFAOYSA-N 0.000 description 1
- KSVIMVISXMCSSS-UHFFFAOYSA-N ethyl 2-methyl-3-[[4-(2-phenylethenyl)phenyl]methyl]benzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2N=C(C)N1CC(C=C1)=CC=C1C=CC1=CC=CC=C1 KSVIMVISXMCSSS-UHFFFAOYSA-N 0.000 description 1
- VHHDHMUBFCUSLS-UHFFFAOYSA-N ethyl 2-methyl-3-[[4-(2-phenylethyl)phenyl]methyl]benzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2N=C(C)N1CC(C=C1)=CC=C1CCC1=CC=CC=C1 VHHDHMUBFCUSLS-UHFFFAOYSA-N 0.000 description 1
- NUJBTXFFJUGENN-UHFFFAOYSA-N ethyl 3,4-diaminobenzoate Chemical compound CCOC(=O)C1=CC=C(N)C(N)=C1 NUJBTXFFJUGENN-UHFFFAOYSA-N 0.000 description 1
- TVJBORKYJFGNKC-UHFFFAOYSA-N ethyl 3-(3-naphthalen-2-ylpropanoylamino)-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCC=2C=C3C=CC=CC3=CC=2)=C1 TVJBORKYJFGNKC-UHFFFAOYSA-N 0.000 description 1
- AFXFOSRHTATTKS-UHFFFAOYSA-N ethyl 3-(cyclobutanecarbonylamino)-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)C2CCC2)=C1 AFXFOSRHTATTKS-UHFFFAOYSA-N 0.000 description 1
- JMCVXQJUVRSVFM-UHFFFAOYSA-N ethyl 3-[(2,4-dichlorophenyl)methyl]-2-(methoxymethyl)benzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2N=C(COC)N1CC1=CC=C(Cl)C=C1Cl JMCVXQJUVRSVFM-UHFFFAOYSA-N 0.000 description 1
- HMGXQWVHJUGWCB-UHFFFAOYSA-N ethyl 3-[(2,4-dichlorophenyl)methyl]-2-methylbenzimidazole-4-carboxylate Chemical compound C1=2C(C(=O)OCC)=CC=CC=2N=C(C)N1CC1=CC=C(Cl)C=C1Cl HMGXQWVHJUGWCB-UHFFFAOYSA-N 0.000 description 1
- ZGPBDYDBUYOPER-UHFFFAOYSA-N ethyl 3-[(2,4-dichlorophenyl)methyl]-2-methylbenzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2N=C(C)N1CC1=CC=C(Cl)C=C1Cl ZGPBDYDBUYOPER-UHFFFAOYSA-N 0.000 description 1
- MYWNTKBVBBOFFU-UHFFFAOYSA-N ethyl 3-[(2,6-dichlorophenyl)methyl]-2-methylbenzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2N=C(C)N1CC1=C(Cl)C=CC=C1Cl MYWNTKBVBBOFFU-UHFFFAOYSA-N 0.000 description 1
- OSBPKRBXWFSPDJ-UHFFFAOYSA-N ethyl 3-[(2-chlorophenyl)methyl-(cyclobutanecarbonyl)amino]-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(N(CC=2C(=CC=CC=2)Cl)C(=O)C2CCC2)=C1 OSBPKRBXWFSPDJ-UHFFFAOYSA-N 0.000 description 1
- GUIKFCJYHASTDO-UHFFFAOYSA-N ethyl 3-[(2-chlorophenyl)methyl]-2-methylbenzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2N=C(C)N1CC1=CC=CC=C1Cl GUIKFCJYHASTDO-UHFFFAOYSA-N 0.000 description 1
- RAERZVRRTKPZTD-UHFFFAOYSA-N ethyl 3-[(2-chlorophenyl)methyl]-2-pentylbenzimidazole-5-carboxylate Chemical compound CCCCCC1=NC2=CC=C(C(=O)OCC)C=C2N1CC1=CC=CC=C1Cl RAERZVRRTKPZTD-UHFFFAOYSA-N 0.000 description 1
- CWTRRJCOZGCPLM-UHFFFAOYSA-N ethyl 3-[(2-chlorophenyl)methyl]-2-propan-2-ylbenzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2N=C(C(C)C)N1CC1=CC=CC=C1Cl CWTRRJCOZGCPLM-UHFFFAOYSA-N 0.000 description 1
- NAYNSUCIIZXHSL-UHFFFAOYSA-N ethyl 3-[(2-chlorophenyl)methyl]-2-propylbenzimidazole-5-carboxylate Chemical compound CCCC1=NC2=CC=C(C(=O)OCC)C=C2N1CC1=CC=CC=C1Cl NAYNSUCIIZXHSL-UHFFFAOYSA-N 0.000 description 1
- KSXVQNVFLZFJFB-UHFFFAOYSA-N ethyl 3-[(2-methoxyacetyl)-[(4-phenylphenyl)methyl]amino]-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(N(CC=2C=CC(=CC=2)C=2C=CC=CC=2)C(=O)COC)=C1 KSXVQNVFLZFJFB-UHFFFAOYSA-N 0.000 description 1
- ZHYNKHIABJIRML-UHFFFAOYSA-N ethyl 3-[(3,4-dichlorophenyl)methyl]-2-methylbenzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2N=C(C)N1CC1=CC=C(Cl)C(Cl)=C1 ZHYNKHIABJIRML-UHFFFAOYSA-N 0.000 description 1
- CFHUNAYNYZEONM-UHFFFAOYSA-N ethyl 3-[(3-fluorophenyl)methyl]-2-propylbenzimidazole-5-carboxylate Chemical compound CCCC1=NC2=CC=C(C(=O)OCC)C=C2N1CC1=CC=CC(F)=C1 CFHUNAYNYZEONM-UHFFFAOYSA-N 0.000 description 1
- HWZHGROMGUCRAP-UHFFFAOYSA-N ethyl 3-[(3-methylphenyl)methyl]-2-propylbenzimidazole-5-carboxylate Chemical compound CCCC1=NC2=CC=C(C(=O)OCC)C=C2N1CC1=CC=CC(C)=C1 HWZHGROMGUCRAP-UHFFFAOYSA-N 0.000 description 1
- IDCMLCRTTKTKMQ-UHFFFAOYSA-N ethyl 3-[(4-bromo-2-fluorophenyl)methyl]-2-butylbenzimidazole-5-carboxylate Chemical compound CCCCC1=NC2=CC=C(C(=O)OCC)C=C2N1CC1=CC=C(Br)C=C1F IDCMLCRTTKTKMQ-UHFFFAOYSA-N 0.000 description 1
- IIUKIXFMTSJOIT-UHFFFAOYSA-N ethyl 3-[(4-fluorophenyl)methyl]-2-propylbenzimidazole-5-carboxylate Chemical compound CCCC1=NC2=CC=C(C(=O)OCC)C=C2N1CC1=CC=C(F)C=C1 IIUKIXFMTSJOIT-UHFFFAOYSA-N 0.000 description 1
- BBEVDQJYEXJNFC-UHFFFAOYSA-N ethyl 3-[(4-tert-butylphenyl)methyl]-2-methylbenzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2N=C(C)N1CC1=CC=C(C(C)(C)C)C=C1 BBEVDQJYEXJNFC-UHFFFAOYSA-N 0.000 description 1
- LVLOHNSNPOMICS-UHFFFAOYSA-N ethyl 3-[3-(2,4-dichlorophenyl)propanoylamino]-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCC=2C(=CC(Cl)=CC=2)Cl)=C1 LVLOHNSNPOMICS-UHFFFAOYSA-N 0.000 description 1
- YZFXIVLFNWEKOU-UHFFFAOYSA-N ethyl 3-[3-(2,6-dichlorophenyl)propanoylamino]-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCC=2C(=CC=CC=2Cl)Cl)=C1 YZFXIVLFNWEKOU-UHFFFAOYSA-N 0.000 description 1
- LCODJSPSSFJYIR-UHFFFAOYSA-N ethyl 3-[3-(2-methoxyphenyl)propanoylamino]-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCC=2C(=CC=CC=2)OC)=C1 LCODJSPSSFJYIR-UHFFFAOYSA-N 0.000 description 1
- KKGWBHMAFQGPKF-UHFFFAOYSA-N ethyl 3-[3-(2-methylphenyl)propanoylamino]-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCC=2C(=CC=CC=2)C)=C1 KKGWBHMAFQGPKF-UHFFFAOYSA-N 0.000 description 1
- KUHVKYHBLNLOQI-UHFFFAOYSA-N ethyl 3-[3-(3,4-dichlorophenyl)propanoylamino]-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCC=2C=C(Cl)C(Cl)=CC=2)=C1 KUHVKYHBLNLOQI-UHFFFAOYSA-N 0.000 description 1
- ZNNJHZRLSBDYFI-UHFFFAOYSA-N ethyl 3-[3-(4-tert-butylphenyl)propanoylamino]-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCC=2C=CC(=CC=2)C(C)(C)C)=C1 ZNNJHZRLSBDYFI-UHFFFAOYSA-N 0.000 description 1
- ZKVBAAKKJBRKRP-UHFFFAOYSA-N ethyl 3-[3-[4-(2-cyanophenyl)phenyl]propanoylamino]-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCC=2C=CC(=CC=2)C=2C(=CC=CC=2)C#N)=C1 ZKVBAAKKJBRKRP-UHFFFAOYSA-N 0.000 description 1
- BPFPTHBXSWOJJH-UHFFFAOYSA-N ethyl 3-[5-(2-bromophenyl)pentanoylamino]-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCCCC=2C(=CC=CC=2)Br)=C1 BPFPTHBXSWOJJH-UHFFFAOYSA-N 0.000 description 1
- MGKNLKIQLIOJTH-UHFFFAOYSA-N ethyl 3-[5-(3-chlorophenyl)pentanoylamino]-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCCCC=2C=C(Cl)C=CC=2)=C1 MGKNLKIQLIOJTH-UHFFFAOYSA-N 0.000 description 1
- RKPCNXCDYCBGCX-UHFFFAOYSA-N ethyl 3-[5-(3-fluorophenyl)pentanoylamino]-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCCCC=2C=C(F)C=CC=2)=C1 RKPCNXCDYCBGCX-UHFFFAOYSA-N 0.000 description 1
- VOBAONRDJXETCN-UHFFFAOYSA-N ethyl 3-[5-(4-chlorophenyl)pentanoylamino]-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCCCC=2C=CC(Cl)=CC=2)=C1 VOBAONRDJXETCN-UHFFFAOYSA-N 0.000 description 1
- ZECVZMXRYUAWLM-UHFFFAOYSA-N ethyl 3-[acetyl-[(2-fluoro-4-phenylphenyl)methyl]amino]-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(N(CC=2C(=CC(=CC=2)C=2C=CC=CC=2)F)C(C)=O)=C1 ZECVZMXRYUAWLM-UHFFFAOYSA-N 0.000 description 1
- ARQRTQQAFNQCID-UHFFFAOYSA-N ethyl 3-[cyclopropanecarbonyl-[(2-fluorophenyl)methyl]amino]-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(N(CC=2C(=CC=CC=2)F)C(=O)C2CC2)=C1 ARQRTQQAFNQCID-UHFFFAOYSA-N 0.000 description 1
- PJIPNRWWHNGBFO-UHFFFAOYSA-N ethyl 3-[methyl-(2-phenylacetyl)amino]-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(N(C)C(=O)CC=2C=CC=CC=2)=C1 PJIPNRWWHNGBFO-UHFFFAOYSA-N 0.000 description 1
- LOYGLFWBPQYKOA-UHFFFAOYSA-N ethyl 3-benzamido-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)C=2C=CC=CC=2)=C1 LOYGLFWBPQYKOA-UHFFFAOYSA-N 0.000 description 1
- CEXOPGRYXRUSNP-UHFFFAOYSA-N ethyl 3-benzyl-2-methylbenzimidazole-5-carboxylate Chemical compound C12=CC(C(=O)OCC)=CC=C2N=C(C)N1CC1=CC=CC=C1 CEXOPGRYXRUSNP-UHFFFAOYSA-N 0.000 description 1
- ZITSNNHRIIFDHF-UHFFFAOYSA-N ethyl 3-butyl-2-propylbenzimidazole-5-carboxylate Chemical compound C1=C(C(=O)OCC)C=C2N(CCCC)C(CCC)=NC2=C1 ZITSNNHRIIFDHF-UHFFFAOYSA-N 0.000 description 1
- YUCBAGCLBRQHCJ-UHFFFAOYSA-N ethyl 4-[3-(2,4-dichlorophenyl)propanoylamino]-3-nitrobenzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OCC)=CC=C1NC(=O)CCC1=CC=C(Cl)C=C1Cl YUCBAGCLBRQHCJ-UHFFFAOYSA-N 0.000 description 1
- QAZGZSKIQYKACR-UHFFFAOYSA-N ethyl 4-[3-(2-chlorophenyl)propanoylamino]-3-nitrobenzoate Chemical compound [O-][N+](=O)C1=CC(C(=O)OCC)=CC=C1NC(=O)CCC1=CC=CC=C1Cl QAZGZSKIQYKACR-UHFFFAOYSA-N 0.000 description 1
- HPCYANYWTUCLMH-UHFFFAOYSA-N ethyl 4-amino-3-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C(N)C([N+]([O-])=O)=C1 HPCYANYWTUCLMH-UHFFFAOYSA-N 0.000 description 1
- KXOUJBYLXVJRKI-UHFFFAOYSA-N ethyl 4-nitro-3-(3-phenylpropanoylamino)benzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCC=2C=CC=CC=2)=C1 KXOUJBYLXVJRKI-UHFFFAOYSA-N 0.000 description 1
- YALHGSLWPDFDIP-UHFFFAOYSA-N ethyl 4-nitro-3-(5-phenylpentanoylamino)benzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCCCC=2C=CC=CC=2)=C1 YALHGSLWPDFDIP-UHFFFAOYSA-N 0.000 description 1
- XIZJTVLBCIQRPU-UHFFFAOYSA-N ethyl 4-nitro-3-(octanoylamino)benzoate Chemical compound CCCCCCCC(=O)NC1=CC(C(=O)OCC)=CC=C1[N+]([O-])=O XIZJTVLBCIQRPU-UHFFFAOYSA-N 0.000 description 1
- LBOIHYMIPNEZGY-UHFFFAOYSA-N ethyl 4-nitro-3-(pentanoylamino)benzoate Chemical compound CCCCC(=O)NC1=CC(C(=O)OCC)=CC=C1[N+]([O-])=O LBOIHYMIPNEZGY-UHFFFAOYSA-N 0.000 description 1
- PBJOJOABBJZNKV-UHFFFAOYSA-N ethyl 4-nitro-3-(propanoylamino)benzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CC)=C1 PBJOJOABBJZNKV-UHFFFAOYSA-N 0.000 description 1
- OCLSPKLATDYOEY-UHFFFAOYSA-N ethyl 4-nitro-3-[3-(2-phenylphenyl)propanoylamino]benzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCC=2C(=CC=CC=2)C=2C=CC=CC=2)=C1 OCLSPKLATDYOEY-UHFFFAOYSA-N 0.000 description 1
- MDWAOLBIKGCHLB-UHFFFAOYSA-N ethyl 4-nitro-3-[3-(4-phenylmethoxyphenyl)propanoylamino]benzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCC=2C=CC(OCC=3C=CC=CC=3)=CC=2)=C1 MDWAOLBIKGCHLB-UHFFFAOYSA-N 0.000 description 1
- PQLDFTIISUZULA-UHFFFAOYSA-N ethyl 4-nitro-3-[3-[2-(trifluoromethyl)phenyl]propanoylamino]benzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCC=2C(=CC=CC=2)C(F)(F)F)=C1 PQLDFTIISUZULA-UHFFFAOYSA-N 0.000 description 1
- FJYDSOULLGLLGS-UHFFFAOYSA-N ethyl 4-nitro-3-[4-(4-phenylphenyl)butanoylamino]benzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C(NC(=O)CCCC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 FJYDSOULLGLLGS-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000002541 furyl group Chemical group 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
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- RMSHYQAVCSUECE-UHFFFAOYSA-N hexane-1-sulfonamide Chemical compound CCCCCCS(N)(=O)=O RMSHYQAVCSUECE-UHFFFAOYSA-N 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000015122 lemonade Nutrition 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
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- ZTYZEUXZHGOXRT-UHFFFAOYSA-N quinoline-8-sulfonamide Chemical compound C1=CN=C2C(S(=O)(=O)N)=CC=CC2=C1 ZTYZEUXZHGOXRT-UHFFFAOYSA-N 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP34342595 | 1995-12-28 | ||
JP28767696 | 1996-10-08 | ||
PCT/JP1996/003858 WO1997024334A1 (fr) | 1995-12-28 | 1996-12-27 | Derives du benzimidazole |
Publications (2)
Publication Number | Publication Date |
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IL124969A0 IL124969A0 (en) | 1999-01-26 |
IL124969A true IL124969A (he) | 2002-09-12 |
Family
ID=26556834
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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IL12496996A IL124969A (he) | 1995-12-28 | 1996-12-27 | תולדות בנזאימידזול, תהליכים להכנתן ותכשירי רוקחות המכילים אותן |
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US (2) | US6166219A (he) |
EP (1) | EP0882718B1 (he) |
JP (2) | JP3063162B2 (he) |
CN (1) | CN1211238A (he) |
AT (1) | ATE303365T1 (he) |
AU (1) | AU722514B2 (he) |
BR (1) | BR9612434A (he) |
DE (1) | DE69635135T2 (he) |
DK (1) | DK0882718T3 (he) |
EA (1) | EA002357B1 (he) |
ES (1) | ES2244979T3 (he) |
HU (1) | HUP9900625A3 (he) |
IL (1) | IL124969A (he) |
NZ (1) | NZ324834A (he) |
TR (1) | TR199801249T2 (he) |
WO (1) | WO1997024334A1 (he) |
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- 1996-12-27 DK DK96943331T patent/DK0882718T3/da active
- 1996-12-27 CN CN96180137A patent/CN1211238A/zh active Pending
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DK0882718T3 (da) | 2005-12-12 |
JP2000159749A (ja) | 2000-06-13 |
ATE303365T1 (de) | 2005-09-15 |
US6352985B1 (en) | 2002-03-05 |
EP0882718A4 (en) | 1999-08-04 |
AU722514B2 (en) | 2000-08-03 |
DE69635135T2 (de) | 2006-07-06 |
DE69635135D1 (en) | 2005-10-06 |
CN1211238A (zh) | 1999-03-17 |
WO1997024334A1 (fr) | 1997-07-10 |
BR9612434A (pt) | 1999-12-28 |
JP3063162B2 (ja) | 2000-07-12 |
AU1209597A (en) | 1997-07-28 |
ES2244979T3 (es) | 2005-12-16 |
EP0882718A1 (en) | 1998-12-09 |
EA002357B1 (ru) | 2002-04-25 |
US6166219A (en) | 2000-12-26 |
HUP9900625A3 (en) | 2003-04-28 |
EA199800609A1 (ru) | 1999-02-25 |
IL124969A0 (en) | 1999-01-26 |
EP0882718B1 (en) | 2005-08-31 |
TR199801249T2 (xx) | 1998-10-21 |
NZ324834A (en) | 2001-11-30 |
HUP9900625A2 (hu) | 1999-06-28 |
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