JP2001505193A - ベンズアミド誘導体 - Google Patents
ベンズアミド誘導体Info
- Publication number
- JP2001505193A JP2001505193A JP52122598A JP52122598A JP2001505193A JP 2001505193 A JP2001505193 A JP 2001505193A JP 52122598 A JP52122598 A JP 52122598A JP 52122598 A JP52122598 A JP 52122598A JP 2001505193 A JP2001505193 A JP 2001505193A
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- methyl
- amino
- acyl
- lower alkyl
- 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.)
- Granted
Links
- 150000003936 benzamides Chemical class 0.000 title abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 222
- 150000003839 salts Chemical class 0.000 claims abstract description 160
- 238000000034 method Methods 0.000 claims abstract description 100
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 88
- 125000003118 aryl group Chemical group 0.000 claims abstract description 88
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 87
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- 229960003726 vasopressin Drugs 0.000 claims abstract description 10
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 claims abstract description 9
- 108010004977 Vasopressins Proteins 0.000 claims abstract description 9
- 102000002852 Vasopressins Human genes 0.000 claims abstract description 9
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 claims abstract description 9
- 239000003814 drug Substances 0.000 claims abstract description 6
- -1 N-protected guanidino Chemical group 0.000 claims description 542
- 150000001875 compounds Chemical class 0.000 claims description 323
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 172
- 238000004519 manufacturing process Methods 0.000 claims description 148
- 125000003282 alkyl amino group Chemical group 0.000 claims description 129
- 125000002252 acyl group Chemical group 0.000 claims description 127
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 124
- 239000002253 acid Substances 0.000 claims description 57
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 41
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 40
- 230000014509 gene expression Effects 0.000 claims description 34
- 125000004423 acyloxy group Chemical group 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 32
- 150000002367 halogens Chemical class 0.000 claims description 32
- 125000004442 acylamino group Chemical group 0.000 claims description 30
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 26
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 19
- 239000003638 chemical reducing agent Substances 0.000 claims description 19
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 18
- 125000001041 indolyl group Chemical group 0.000 claims description 17
- 239000002585 base Substances 0.000 claims description 16
- 238000003379 elimination reaction Methods 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000004076 pyridyl group Chemical class 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- 241001024304 Mino Species 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 8
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 8
- 125000005276 alkyl hydrazino group Chemical group 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 6
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 6
- 241001465754 Metazoa Species 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 5
- 125000005936 piperidyl group Chemical group 0.000 claims description 5
- 208000011580 syndromic disease Diseases 0.000 claims description 5
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 5
- 206010003445 Ascites Diseases 0.000 claims description 4
- 206010016654 Fibrosis Diseases 0.000 claims description 4
- 206010019280 Heart failures Diseases 0.000 claims description 4
- 241000282412 Homo Species 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 208000019025 Hypokalemia Diseases 0.000 claims description 4
- 206010021036 Hyponatraemia Diseases 0.000 claims description 4
- 208000027530 Meniere disease Diseases 0.000 claims description 4
- 206010030113 Oedema Diseases 0.000 claims description 4
- 208000001647 Renal Insufficiency Diseases 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 230000007882 cirrhosis Effects 0.000 claims description 4
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 201000006370 kidney failure Diseases 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 201000003152 motion sickness Diseases 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 208000024896 potassium deficiency disease Diseases 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 230000028327 secretion Effects 0.000 claims description 4
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 244000007835 Cyamopsis tetragonoloba Species 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 3
- 230000002159 abnormal effect Effects 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 3
- 210000004369 blood Anatomy 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 3
- 235000010288 sodium nitrite Nutrition 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 238000007257 deesterification reaction Methods 0.000 claims 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims 2
- URLFAYHEJINHBH-UHFFFAOYSA-N (c-phenoxy-n-sulfamoylcarbonimidoyl)oxybenzene Chemical compound C=1C=CC=CC=1OC(=NS(=O)(=O)N)OC1=CC=CC=C1 URLFAYHEJINHBH-UHFFFAOYSA-N 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 229940015043 glyoxal Drugs 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 177
- 230000008485 antagonism Effects 0.000 abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 228
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 187
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 167
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 161
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 158
- 238000006243 chemical reaction Methods 0.000 description 158
- 230000002829 reductive effect Effects 0.000 description 132
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 128
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 127
- 239000002904 solvent Substances 0.000 description 124
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 105
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 96
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 82
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 80
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 79
- 229960001701 chloroform Drugs 0.000 description 79
- 239000011541 reaction mixture Substances 0.000 description 72
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 70
- 239000012044 organic layer Substances 0.000 description 69
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 64
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 63
- 235000019341 magnesium sulphate Nutrition 0.000 description 63
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 61
- 239000012267 brine Substances 0.000 description 55
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 55
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 49
- 229920006395 saturated elastomer Polymers 0.000 description 49
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 39
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 39
- 235000017557 sodium bicarbonate Nutrition 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
- 238000001816 cooling Methods 0.000 description 31
- 229910052757 nitrogen Inorganic materials 0.000 description 31
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
- 239000003054 catalyst Substances 0.000 description 29
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 28
- 239000000843 powder Substances 0.000 description 28
- 238000006722 reduction reaction Methods 0.000 description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 238000010438 heat treatment Methods 0.000 description 24
- 239000012043 crude product Substances 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
- 235000011054 acetic acid Nutrition 0.000 description 20
- 239000007864 aqueous solution Substances 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 18
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 18
- 238000012746 preparative thin layer chromatography Methods 0.000 description 18
- 239000007858 starting material Substances 0.000 description 18
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- IGGHBQMZERWHGY-UHFFFAOYSA-N 2-isocyanatobenzamide Chemical compound NC(=O)C1=CC=CC=C1N=C=O IGGHBQMZERWHGY-UHFFFAOYSA-N 0.000 description 16
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
- 230000002411 adverse Effects 0.000 description 16
- 238000010992 reflux Methods 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- 238000010898 silica gel chromatography Methods 0.000 description 16
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 15
- 238000004440 column chromatography Methods 0.000 description 15
- 239000011780 sodium chloride Substances 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
- 150000001408 amides Chemical class 0.000 description 13
- 150000001412 amines Chemical class 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 229910052763 palladium Inorganic materials 0.000 description 13
- 229910052697 platinum Inorganic materials 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 150000003973 alkyl amines Chemical class 0.000 description 12
- 239000012141 concentrate Substances 0.000 description 12
- 235000008504 concentrate Nutrition 0.000 description 12
- 229910052802 copper Inorganic materials 0.000 description 12
- 239000010949 copper Substances 0.000 description 12
- 239000003480 eluent Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 238000000746 purification Methods 0.000 description 11
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- 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 10
- 239000000872 buffer Substances 0.000 description 10
- 238000010531 catalytic reduction reaction Methods 0.000 description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 description 10
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 229910017052 cobalt Inorganic materials 0.000 description 9
- 239000010941 cobalt Substances 0.000 description 9
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 9
- 235000019253 formic acid Nutrition 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 229910052742 iron Inorganic materials 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 9
- 125000002911 monocyclic heterocycle group Chemical group 0.000 description 9
- 150000007524 organic acids Chemical class 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 238000003828 vacuum filtration Methods 0.000 description 9
- GTKIGDZXPDCIKR-UHFFFAOYSA-N 2-phenylbenzamide Chemical compound NC(=O)C1=CC=CC=C1C1=CC=CC=C1 GTKIGDZXPDCIKR-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
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
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- UMGLSMYSWIQHOX-UHFFFAOYSA-N benzyl 1h-indole-7-carboxylate Chemical compound C=1C=CC=2C=CNC=2C=1C(=O)OCC1=CC=CC=C1 UMGLSMYSWIQHOX-UHFFFAOYSA-N 0.000 description 1
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- HFVIRUFDGPJMRB-UHFFFAOYSA-N benzyl 2-methyl-1h-indole-4-carboxylate Chemical compound C1=CC=C2NC(C)=CC2=C1C(=O)OCC1=CC=CC=C1 HFVIRUFDGPJMRB-UHFFFAOYSA-N 0.000 description 1
- UUZYBYIOAZTMGC-UHFFFAOYSA-M benzyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1=CC=CC=C1 UUZYBYIOAZTMGC-UHFFFAOYSA-M 0.000 description 1
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- 125000001246 bromo group Chemical group Br* 0.000 description 1
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- 230000006837 decompression Effects 0.000 description 1
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- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- WACIUSZPMGWDDT-UHFFFAOYSA-N methyl 2-(phenylmethoxymethyl)-1h-indole-4-carboxylate Chemical compound C=1C=2C(C(=O)OC)=CC=CC=2NC=1COCC1=CC=CC=C1 WACIUSZPMGWDDT-UHFFFAOYSA-N 0.000 description 1
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- QBMIZUODWFIZER-UHFFFAOYSA-N methyl 2-methoxy-4-[[2-(3-oxa-1-azaspiro[4.4]non-1-en-2-yl)phenyl]carbamoyl]benzoate Chemical compound C1=C(OC)C(C(=O)OC)=CC=C1C(=O)NC1=CC=CC=C1C(OC1)=NC11CCCC1 QBMIZUODWFIZER-UHFFFAOYSA-N 0.000 description 1
- SQVLNVWYATVXRP-UHFFFAOYSA-N methyl 2-methoxy-4-[methyl-[2-(3-oxa-1-azaspiro[4.4]non-1-en-2-yl)phenyl]carbamoyl]benzoate Chemical compound C1=C(OC)C(C(=O)OC)=CC=C1C(=O)N(C)C1=CC=CC=C1C(OC1)=NC11CCCC1 SQVLNVWYATVXRP-UHFFFAOYSA-N 0.000 description 1
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- 239000002808 molecular sieve Substances 0.000 description 1
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- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 description 1
- MKDYQLJYEBWUIG-UHFFFAOYSA-N n',n'-diethyl-n-methylethane-1,2-diamine Chemical compound CCN(CC)CCNC MKDYQLJYEBWUIG-UHFFFAOYSA-N 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- ZUNASKGUWIJFOS-UHFFFAOYSA-N n,4-dimethyl-1h-benzimidazole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)NC)=NC2=C1C ZUNASKGUWIJFOS-UHFFFAOYSA-N 0.000 description 1
- YJFJFLHDNNONLT-UHFFFAOYSA-N n,n,n'-trimethyl-n'-(4-nitro-1h-benzimidazol-2-yl)ethane-1,2-diamine Chemical compound C1=CC=C2NC(N(C)CCN(C)C)=NC2=C1[N+]([O-])=O YJFJFLHDNNONLT-UHFFFAOYSA-N 0.000 description 1
- MUUBDUDARGVKDZ-UHFFFAOYSA-N n,n-dimethyl-4-nitro-1h-benzimidazol-2-amine Chemical compound C1=CC=C2NC(N(C)C)=NC2=C1[N+]([O-])=O MUUBDUDARGVKDZ-UHFFFAOYSA-N 0.000 description 1
- VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
- KJQNAIWETOXIFK-UHFFFAOYSA-N n-(3-chloropropyl)-2-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)NCCCCl KJQNAIWETOXIFK-UHFFFAOYSA-N 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- FFAFFDVMMZSFJY-UHFFFAOYSA-N n-[1-(hydroxymethyl)cyclopentyl]-2-nitrobenzamide Chemical compound C=1C=CC=C([N+]([O-])=O)C=1C(=O)NC1(CO)CCCC1 FFAFFDVMMZSFJY-UHFFFAOYSA-N 0.000 description 1
- YIZNYLGACDXIQS-UHFFFAOYSA-N n-[2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)phenyl]-3-methoxy-4-nitrobenzamide Chemical compound C1=C([N+]([O-])=O)C(OC)=CC(C(=O)NC=2C(=CC=CC=2)C=2OCC(C)(C)N=2)=C1 YIZNYLGACDXIQS-UHFFFAOYSA-N 0.000 description 1
- WHUWHVXQUAPIAU-UHFFFAOYSA-N n-[2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)phenyl]-3-methoxy-n-methyl-4-nitrobenzamide Chemical compound C1=C([N+]([O-])=O)C(OC)=CC(C(=O)N(C)C=2C(=CC=CC=2)C=2OCC(C)(C)N=2)=C1 WHUWHVXQUAPIAU-UHFFFAOYSA-N 0.000 description 1
- RMEUSCOSQGYNIC-UHFFFAOYSA-N n-[2-methoxy-4-[methyl-[4-methyl-2-[6-(4-methylpiperazin-1-yl)-6-oxohexoxy]phenyl]carbamoyl]phenyl]-3-nitro-2-[(2,2,2-trifluoroacetyl)amino]benzamide Chemical compound COC1=CC(C(=O)N(C)C=2C(=CC(C)=CC=2)OCCCCCC(=O)N2CCN(C)CC2)=CC=C1NC(=O)C1=CC=CC([N+]([O-])=O)=C1NC(=O)C(F)(F)F RMEUSCOSQGYNIC-UHFFFAOYSA-N 0.000 description 1
- SEELCNJAGDDXQS-UHFFFAOYSA-N n-[2-methoxy-4-[methyl-[4-methyl-2-[6-(4-methylpiperazin-1-yl)-6-oxohexoxy]phenyl]carbamoyl]phenyl]quinoxaline-5-carboxamide Chemical compound C=1C=C(NC(=O)C=2C3=NC=CN=C3C=CC=2)C(OC)=CC=1C(=O)N(C)C1=CC=C(C)C=C1OCCCCCC(=O)N1CCN(C)CC1 SEELCNJAGDDXQS-UHFFFAOYSA-N 0.000 description 1
- WYMPUJDJBMISEZ-UHFFFAOYSA-N n-[4-[(2-amino-4-methylphenyl)-methylcarbamoyl]-2-methoxyphenyl]-2-methyl-1h-benzimidazole-4-carboxamide Chemical compound C=1C=C(NC(=O)C=2C=3N=C(C)NC=3C=CC=2)C(OC)=CC=1C(=O)N(C)C1=CC=C(C)C=C1N WYMPUJDJBMISEZ-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- PXSXRABJBXYMFT-UHFFFAOYSA-N n-hexylhexan-1-amine Chemical compound CCCCCCNCCCCCC PXSXRABJBXYMFT-UHFFFAOYSA-N 0.000 description 1
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 0.000 description 1
- JACMPVXHEARCBO-UHFFFAOYSA-N n-pentylpentan-1-amine Chemical compound CCCCCNCCCCC JACMPVXHEARCBO-UHFFFAOYSA-N 0.000 description 1
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- RVQZKNOMKUSGCI-UHFFFAOYSA-N pyridine-4-carbonyl chloride Chemical compound ClC(=O)C1=CC=NC=C1 RVQZKNOMKUSGCI-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical compound C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000001422 pyrrolinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 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
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008279 sol Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- OOVPQKQFSDFRFA-UHFFFAOYSA-N tert-butyl 3-(hydroxymethyl)indole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C=C(CO)C2=C1 OOVPQKQFSDFRFA-UHFFFAOYSA-N 0.000 description 1
- ACVIQZCQEKGWCD-UHFFFAOYSA-N tert-butyl 4-[[4-[[2-(4,4-dimethyl-5h-1,3-oxazol-2-yl)phenyl]-methylcarbamoyl]-2-methoxybenzoyl]amino]benzimidazole-1-carboxylate Chemical compound C=1C=C(C(=O)NC=2C=3N=CN(C=3C=CC=2)C(=O)OC(C)(C)C)C(OC)=CC=1C(=O)N(C)C1=CC=CC=C1C1=NC(C)(C)CO1 ACVIQZCQEKGWCD-UHFFFAOYSA-N 0.000 description 1
- LIGDOBPTBWCFLT-UHFFFAOYSA-N tert-butyl 4-amino-2-[2-(dimethylamino)ethylamino]benzimidazole-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC(C)(C)C)C(NCCN(C)C)=NC2=C1N LIGDOBPTBWCFLT-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N tert-butyl alcohol Substances CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ICJDRMANJUBCNJ-UHFFFAOYSA-N tert-butyl n-(4-amino-1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC(C)(C)C)=NC2=C1N ICJDRMANJUBCNJ-UHFFFAOYSA-N 0.000 description 1
- XVFFNGBSMDKKRP-UHFFFAOYSA-N tert-butyl n-(4-nitro-1h-benzimidazol-2-yl)carbamate Chemical compound C1=CC=C2NC(NC(=O)OC(C)(C)C)=NC2=C1[N+]([O-])=O XVFFNGBSMDKKRP-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- AHJWSRRHTXRLAQ-UHFFFAOYSA-N tetramethoxymethane Chemical compound COC(OC)(OC)OC AHJWSRRHTXRLAQ-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 239000003038 vasopressin antagonist Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having carbon atoms of carboxamide groups, amino groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.式 〔式中、 R1はアリール、シクロ低級アルキルまたは複素環基であり、その各々は、ハ ロゲン;ヒドロキシ;ニトロ;保護されたアミノ;アミノ;アシル;置換アシル ;アシル低級アルキルスルフィニル;アシル低級アルキルスルホニル;アシルオ キシ;低級アルキルアミノ低級アルキルカルバモイルオキシ;アリール;シアノ ;複素環基;アシル、置換アシル、アリールもしくはアシル置換アリールで置換 されていてもよい低級アルケニル;アミノ、アシルアミノもしくは置換アシルア ミノで置換されていてもよい低級アルキニル;ハロゲン、アミノ、低級アルキル アミノ、アシルアミノ、置換アシルアミノ、ヒドロキシ、アシルオキシ、アシル 低級アルカノイルオキシ、アシル、置換アシル、アシル低級アルコキシイミノ、 アリールもしくはアシル置換アリールで置換されていてもよい低級アルキル;ア シルもしくは置換アシルで置換されていてもよい低級アルキルチオ;アリール、 置換アリール、ヒドロキシ、アシルオキシ、アミノ、低級アルキルアミノ、保護 されたアミノ、複素環基、アシル置換ピリジル、置換アシル置換ピリジル、ハロ ゲン、アシル低級アルキルアミノ、N−保護されたアシル低級アルキルアミノ、 N−アシル低級アルキル−N−低級アルキルアミノ、アシル、置換アシル、アシ ルアミノ、置換アシルアミノ、低級アルキルヒドラジノカルボニルアミノ、ヒド ロキシイミノ、アシル低級アルコキシイミノ、置換アシル低級アルコキシイミノ 、アシル低級アルコキシ、グアニジノもしくはN−保護されたグアニジノで置換 されていてもよいアルコキシ;およびアシルもしくは置換アシルで置換されてい てもよい低級アルケニルオキシからなる群から選ばれた置換基で置換されていて もよく; R2は水素;ヒドロキシ、アリールもしくはアシルで置換されていてもよい低 級アルキル;またはシクロ低級アルキルであり; R3は水素;ハロゲン;ヒドロキシ;アシルオキシ;置換アシルオキシ;ヒド ロキシもしくは低級アルコキシで置換されていてもよい低級アルキル;アリール 、アミノ、保護されたアミノ、アシル、ヒドロキシ、シアノもしくは低級アルキ ルチオで置換されていてもよい低級アルコキシ;ニトロ;アミノ;アシル;置換 アシル;またはシクロ低級アルキルオキシであり; Aは単結合、OまたはNHであり; Eは低級アルキレン、低級アルケニレン、−C(=O)−、−SO2−または式 −G−J− (ここに、Gは低級アルキレンまたは−C(=O)−であり、 JはOまたは−N(R4)−(ここに、R4は水素またはN−保護基である)であ る)の基であり; Xは−CH=CH−、−CH=N−またはSであり; Yはアリールであって、アシル、保護されたアミノ低級アルカノイル、保護さ れたアミノおよびニトロ、アミノおよびニトロもしくはジアミノで置換されてい てもよく;もしくは 縮合複素環基であって、ハロゲン、アシル、低級アルコキシ、ヒドロキシ、グア ニジノ、メルカプト、アシルアミノ、アミノ、複索環基、シアノアミノ、アミノ 低級アルキル低級アルキルアミノ、低級アルキルアミノ、低級アルキルアミノ低 級アルキルアミノ、置換複素環基、低級アルキルヒドラジノ、アリールオキシ、 低級アルキルチオ、アリール、保護されたアミノ、N−保護された低級アルキル アミノ低級アルキルアミノ、N−保護されたアミノ低級アルキル(N’−低級ア ルキル)アミノ、アミノ低級アルキル(N−低級アルキル)アミノ、低級アルキ ルアミノ低級アルキル(N−低級アルキル)アミノ、低級アルコキシ低級アルキ ルアミノならびにアリール、アル低級アルコキシ、シアノ、ヒドロキシイミノ、 メルカプト、低級アルキルアミノ、アシルオキシ、ハロゲン、低級アルコキシ、 保護されたヒドロキシ、ヒドロキシ、低級アルコキシアリール、保護されたアミ ノ、アミノ、複素環基もしくは置換複素環基で置換されていてもよい低級アルキ ルからなる群から選ばれた置換基で置換されていてもよい; ただし、Yが低級アルキルもしくはアシルで置換されていてもよいフェニルであ るときには、Aは単結合であり、Eは−C(=O)N(R4)−(ここに、R4は 上に定義した通りである)である〕 の化合物ならびにその医薬として許容される塩。 2. R1がアリール、シクロ低級アルキルまたは複素環基であり、その各々は 、ハロゲン;ヒドロキシ;ニトロ;アミノ;アシル;置換アシル;アシル低級ア ルキルスルフィニル;アシル低級アルキルスルホニル;アシルオキシ;低級アル キルアミノ低級アルキルカルバモイルオキシ;アリール;シアノ;複素環基;ア シル、置換アシル、アリールもしくはアシル置換アリールで置換されていてもよ い低級アルケニル;アミノ、アシルアミノもしくは置換アシルアミノで置換され ていてもよい低級アルキニル;ハロゲン、アミノ、低級アルキルアミノ、アシル アミノ、置換アシルアミノ、ヒドロキシ、アシルオキシ、アシル低級アルカノイ ルオキシ、アシル、置換アシル、アシル低級アルコキシイミノ、アリールもしく はアシル置換アリールで置換されていてもよい低級アルキル;アシルもしくは置 換アシルで置換されていてもよい低級アルキルチオ;アリール、置換アリール、 ヒドロキシ、アシルオキシ、アミノ、低級アルキルアミノ、保護されたアミノ、 複素環基、アシル置換ピリジル、置換アシル置換ピリジル、ハロゲン、アシル低 級アルキルアミノ、N−保護されたアシル低級アルキルアミノ、N−アシル低級 アルキル−N−低級アルキルアミノ、アシル、置換アシル、アシルアミノ、置換 アシルアミノ、低級アルキルヒドラジノカルボニルアミノ、ヒドロキシイミノ、 アシル低級アルコキシイミノ、置換アシル低級アルコキシイミノ、アシル低級ア ルコキシ、グアニジノもしくはN−保護されたグアニジノで置換されていてもよ いアルコキシ;およびアシルもしくは置換アシルで置換されていてもよい低級ア ルケニルオキシからなる群から選ばれた置換基で置換されていてもよく; R2が水素;ヒドロキシ、アリールもしくはアシルで置換されていてもよい低 級アルキル;またはシクロ低級アルキルであり; R3が水素;ハロゲン;ヒドロキシ;アシルオキシ;置換アシルオキシ;ヒド ロキシまたは低級アルコキシで置換されていてもよい低級アルキル;アリール、 アミノ、保護されたアミノ、アシル、ヒドロキシ、シアノもしくは低級アルキル チオで置換されていてもよい低級アルコキシ;ニトロ;アミノ;アシル;置換ア シル;またはシクロ低級アルキルオキシであり; Aは単結合、OまたはNHであり; Eは低級アルキレン、低級アルケニレン、−C(=O)−、−SO2−または式 −G−J− (ここに、Gは低級アルキレンまたは−C(=O)−であり、 JはOまたは−N(R4)−(ここに、R4は水素またはN−保護基である)であ る)の基であり; Xは−CH=CH−、−CH=N−またはSであり; Yは、保護されたアミノおよびニトロ、アミノおよびニトロもしくはジアミノ で置換されたアリールであるか;もしくは縮合複素環であって、ハロゲン、アシ ル、低級アルコキシ、ヒドロキシ、グアニジノ、メルカプト、アシルアミノ、ア ミノならびに低級アルキルアミノ、アシルオキシ、ハロゲン、低級アルコキシ、 保護されたヒドロキシ、ヒドロキシ、低級アルコキシアリール、保護されたアミ ノ、アミノもしくは複素環基で置換されていてもよい低級アルキルからなる群か ら選ばれた置換基で置換されていてもよい請求の範囲第1項記載の化合物。 3. R1が、アシルもしくはアシルアミノで置換された低級アルキルで置換さ れていてもよいアリールであり、 R2が低級アルキルであり、 R3が水素、低級アルキルまたは低級アルコキシであり、 Aが単結合またはNHであり、 Eが−C(=O)−または−C(=O)NH−であり、 Xが−CH=CH−であり、 Yが、低級アルキルアミノ、アシルオキシ、ハロゲン、低級アルコキシ、保護 されたヒドロキシ、ヒドロキシ、低級アルコキシアリール、保護されたアミノ、 アミノもしくは複素環基で置換されていてもよい低級アルキルで置換されている 縮合複素環基である請求の範囲第2項記載の化合物。 4. R1が、各々にN−低級アルキルピペラジニルカルボニル置換低級アルコ キシで置換されているフェニルまたはトリルであり、 R3が低級アルコキシであり、 Aが単結合であり、 Eが−C(=O)NH−であり、 Yが、アミノ、ヒドロキシもしくはN−低級アルキルピペラジニルで置換され ていてもよい低級アルキルで置換されているベンゾイミダゾールである請求の範 囲第3項記載の化合物。 5. R5が、各々にN−低級アルキルピペラジニルカルボニル置換低級アルコ キシで置換されているフェニルまたはトリルであり、 R3が低級アルコキシであり、 AがNHであり、 Eが−C(=O)−であり、 Yが、アミノ、ヒドロキシもしくはN−低級アルキルピペラジニルで置換され ていてもよい低級アルキルで置換されているベンゾイミダゾールである請求の範 囲第3項記載の化合物。 6. 式 〔式中、 R1はアリール、シクロ低級アルキルまたは複素環基であり、その各々は、ハ ロゲン;ヒドロキシ;ニトロ;保護されたアミノ;アミノ;アシル;置換アシル ;アシル低級アルキルスルフィニル;アシル低級アルキルスルホニル;アシルオ キシ;低級アルキルアミノ低級アルキルカルバモイルオキシ;アリール;シアノ ;複素環基;アシル、置換アシル、アリールもしくはアシル置換アリールで置換 されていてもよい低級アルケニル;アミノ、アシルアミノもしくは置換アシルア ミノで置換されていてもよい低級アルキニル;ハロゲン、アミノ、低級アルキル アミノ、アシルアミノ、置換アシルアミノ、ヒドロキシ、アシルオキシ、アシル 低級アルカノイルオキシ、アシル、置換アシル、アシル低級アルコキシイミノ、 アリールもしくはアシル置換アリールで置換されていてもよい低級アルキル;ア シルもしくは置換アシルで置換されていてもよい低級アルキルチオ;アリール、 置換アリール、ヒドロキシ、アシルオキシ、アミノ、低級アルキルアミノ、保護 されたアミノ、複素環基、アシル置換ピリジル、置換アシル置換ピリジル、ハロ ゲン、アシル低級アルキルアミノ、N−保護されたアシル低級アルキルアミノ、 N−アシル低級アルキル−N−低級アルキルアミノ、アシル、置換アシル、アシ ルアミノ、置換アシルアミノ、低級アルキルヒドラジノカルボニルアミノ、ヒド ロキシイミノ、アシル低級アルコキシイミノ、置換アシル低級アルコキシイミノ 、アシル低級アルコキシ、グアニジノもしくはN−保護されたグアニジノで置換 されていてもよいアルコキシ;およびアシルもしくは置換アシルで置換されてい てもよい低級アルケニルオキシからなる群から選ばれた置換基で置換されていて もよく; R2は水索;ヒドロキシ、アリールもしくはアシルで置換されていてもよい低 級アルキル;またはシクロ低級アルキルであり; R3は水素;ハロゲン;ヒドロキシ;アシルオキシ;置換アシルオキシ;ヒド ロキシもしくは低級アルコキシで置換されていてもよい低級アルキル;アリール 、アミノ、保護されたアミノ、アシル、ヒドロキシ、シアノもしくは低級アルキ ルチオで置換されていてもよい低級アルコキシ;ニトロ;アミノ;アシル;置換 アシル;またはシクロ低級アルキルオキシであり; Aは単結合、OまたはNHであり; Eは低級アルキレン、低級アルケニレン、−C(=O)−、−SO2−または式 −G−J− (ここに、Gは低級アルキレンまたは−C(=O)−であり、 JはOまたは−N(R4)−(ここに、R4は水素またはN−保護基である)であ る)の基であり; Xは−CH=CH−、−CH=N−またはSであり; Yはアリールであって、アシル、保護されたアミノ低級アルカノイル、保護さ れたアミノおよびニトロ、アミノおよびニトロもしくはジアミノで置換されてい てもよく;もしくは 縮合複素環基であって、ハロゲン、アシル、低級アルコキシ、ヒドロキシ、グア ニジノ、メルカプト、アシルアミノ、アミノ、複素環基、シアノアミノ、アミノ 低級アルキル低級アルキルアミノ、低級アルキルアミノ、低級アルキルアミノ低 級アルキルアミノ、置換複素環基、低級アルキルヒドラジノ、アリールオキシ、 低級アルキルチオ、アリール、保護されたアミノ、N−保護された低級アルキル アミノ低級アルキルアミノ、N−保護されたアミノ低級アルキル(N’−低級ア ルキル)アミノ、アミノ低級アルキル(N−低級アルキル)アミノ、低級アルキ ルアミノ低級アルキル(N−低級アルキル)アミノ、低級アルコキシ低級アルキ ルアミノならびにアリール、アル低級アルコキシ、シアノ、ヒドロキシイミノ、 メルカプト、低級アルキルアミノ、アシルオキシ、ハロゲン、低級アルコキシ、 保護されたヒドロキシ、ヒドロキシ、低級アルコキシアリール、保護されたアミ ノ、アミノ、複素環基もしくは置換複素環基で置換されていてもよい低級アルキ ルからなる群から選ばれた置換基で置換されていてもよい; ただし、Yが低級アルキルもしくはアシルで置換されていてもよいフェニルであ るときには、Aは単結合であり、Eは−C(=O)N(R4)−(ここに、R4は 上に定義した通りである)である〕 の化合物またはその医薬として許容される塩の製造法であって、 1)式の化合物またはその塩を式 HO−Ea−Y (III) の化合物またはそのカルボキシ基またはスルホ基における反応性誘導体もしくは それらの塩と反応させて、式 の化合物またはその塩を製出する〔上記式中、R1、R2、R3、XおよびYは各 々上に定義した通りであり、Eaは−C(=O)−または−SO2−である〕か、 または、 2)式 の化合物またはその塩を、塩基の存在下に、式 R5−Z1 (IV) の化合物と反応させて、式 の化合物またはその塩を製出する〔上記式中、R1、R2、R3、A、EおよびX は各々上に定義した通りであり、 Yaはインドリルであり、 R5は低級アルキルであり、 Z1は酸残基であり、 YbはN−低級アルキルインドールである〕か、または、 3)式 の化合物またはその塩を還元に付して、式 の化合物またはその塩を製出する〔上記式中、R1、R2、R3、A、EおよびX は各々上に定義した通りであり、 Ycはアミノおよびニトロで置換されたフェニルであり、 Ydはジアミノで置換されたフェニルである〕か、または、 4)式 の化合物またはその塩をハロゲン化アロイル、シアノ低級アルキルカルボン酸、 メルカプト低級アルキルカルボン酸、低級アルキルラクトン、1,1−ジハロ− 1,1−ジフェノキシメタン、N−スルファモイルカルボンイミド酸ジフェニル 、N−シアノカルボンイミド酸ジフェニル、ジシアンジアミド、1,1’−チオ カルボニルイミダゾール、臭化シアン、低級アルコキシカルボニルイソチオシア ナート、オルト蟻酸トリ低級アルキル、オルト炭酸テトラ低級アルキル、低級ア ルキルカルボン酸、ハロ低級アルキルカルボン酸、保護されたアミノ低級アルキ ルカルボニルハロゲン化物または複素環低級アルキルカルボニルハロゲン化物と 反応させて、式 の化合物またはその塩を製出する〔上記式中、R1、R2、R3、A、E、Xおよ びYdは各々上に定義した通りであり、 Yeは、2位においてアリール、フェノキシ、スルファモイルアミノ、シアノア ミノ、グアニジノ、メルカプト、アミノ、低級アルコキシカルボニルアミノ、低 級アルコキシもしくはシアノ、メルカプト、ヒドロキシ、ハロゲン、保護された アミノもしくは複素環基で置換されていてもよい低級アルキルで置換されていて もよいベンゾイミダゾリルである〕か、または、 5)式 の化合物またはその塩をグリオキサールおよび亜硫酸水素ナトリウムと、または 亜硝酸ナトリウムと、反応させて、式 の化合物またはその塩を製出する〔上記式中、R1、R2、R3、A、E、Xおよ びYdは各々上に定義した通りであり、 Yfはキノキサリニルまたはベンゾトリアゾリルである〕か、または、 6)式の化合物またはその塩をアシル化剤と反応させて、式 の化合物またはその塩を製出する〔上記式中、R1、R2、R3、A、E、Xおよ びYaは各々上に定義した通りであり、 YgはN−アシルインドリルである〕か、または、 7)式 の化合物またはその塩をN−置換基脱離反応に付して、式の化合物またはその塩を製出する〔上記式中、R1、R2、R3、A、EおよびX は各々上に定義した通りであり、 Yhは(N−アシル)アシルインドリニル、N−アシルインドリニル、(N−ア シル)ヒドロキシ低級アルキルインドリニル、低級アルキルアミノ低級アルキル アミノ(N−アシル)インドリニル、(N−低級アルコキシアリールメチル)ア シルベンゾイミダゾリル、(N−低級アルコキシカルボニル)フタルイミド低級 アルキルインドリル、N−保護された低級アルキルアミノ低級アルキルアミノ( N−アシル)ベンゾイミダゾリル、(N−アシル)ベンゾイミダゾリル、(N− アシル)低級アルキルベンゾイミダゾリル、N−保護されたアミノ低級アルキル (N−低級アルキル)アミノ(N−アシル)ベンゾイミダゾリル、N−アシルイ ンドリル、(N−アシルオキシメチル)インドリル、(N−アシル)アシルイン ドリル、(N−アリールメチル)低級アルコキシ低級アルキルベンゾイミダゾリ ルまたは(N−低級アルコキシアリールメチル)アシルベンゾイミダゾリルであ り、 Yiはアシルインドリニル、インドリニル、ヒドロキシ低級アルキルインドリニ ル、低級アルキルアミノ低級アルキルアミノインドリニル、アシルベンゾイミダ ゾリル、フタルイミド低級アルキルインドリル、アミノ低級アルキルインドリル 、低級アルキルアミノ低級アルキルアミノベンゾイミダゾリル、ベンゾイミダゾ リル、低級アルキルベンゾイミダゾリル、アミノ低級アルキル(N−低級アルキ ル)アミノベンゾイミダゾリル、インドリル、アシルインドリル、低級アルコキ シ低級アルキルベンゾイミダゾリルまたはアシルベンゾイミダゾリルである〕か 、または、 8)式 の化合物またはその塩をN−保護基脱離反応に付して、式 の化合物またはその塩を製出する〔上記式中、R1、R2、R3、A、EおよびX は各々上に定義した通りであり、 Yjは、保護されたアミノおよびニトロで置換されたアリールであるか、または 、保護されたアミノもしくは保護されたアミノで置換された低級アルキルにより 置換されている縮合複素環基であり、 Ykは、アミノおよびニトロで置換されているアリールであるか、または、アミ ノもしくはアミノ置換低級アルキルにより置換されている縮合複素環基である〕 か、または、 9)式の化合物またはその塩を脱エステル反応に付して、式 の化合物またはその塩を製出する〔上記式中、R1、R2、R3、A、EおよびX は各々上に定義した通りであり、 Ylは、エステル化されたカルボキシで置換されたアリール、またはエステル化 されたカルボキシで置換された縮合複素環基であり、 Ymは、カルボキシで置換されたアリール、またはカルボキシで置換された縮合 複素環基である〕か、または、 10)式 の化合物またはそのカルボキシ基における反応性誘導体もしくはそれらの塩をア ミンまたはその塩と反応させて、式の化合物またはその塩を製出する〔上記式中、R1、R2、R3、A、E、Xおよ びYmは各々上に定義した通りであり、 Ynは、各々に置換または無置換N−含有複素環カルボニル、カルバモイル、複 素環カルバモイルもしくは置換または無置換低級アルキルカルバモイルで置換さ れたアルールもしくは縮合複素環基である〕か、または、 11)式 の化合物またはその塩をメチル基またはヒドロキシ保護基の脱離反応に付して、 式 の化合物またはその塩を製出する〔上記式中、R1、R2、R3、A、EおよびX は各々上に定義した通りであり、 Yoは、各々にメトキシまたは保護されたヒドロキシ置換低級アルキルで置換さ れた縮合(N−アシル)N−含有複素環基もしくは縮合複素環基であり、 Ypは、各々にヒドロキシもしくはヒドロキシ置換低級アルキルで置換された縮 合(N−アシル)N−含有複素環基もしくは縮合複素環基である〕か、または、 12)式 の化合物またはその塩をアシル化剤と反応させて、式 の化合物またはその塩を製出する〔上記式中、R1、R2、R3、A、EおよびX は各々上に定義した通りであり、 Yqは、アミノもしくはアミノ低級アルキルで置換された縮合複素環基であり、 Yrは、アシルアミノもしくはアシルアミノ低級アルキルで置換された縮合複素 環基である〕か、または、 13)式の化合物またはその塩をハロゲン化N−低級アルキルメチレンアンモニウムと反 応させて、式 の化合物またはその塩を製出する〔上記式中、R1、R2、R3、A、E、Xおよ びYaは各々上に定義した通りであり、 Ysは、低級アルキルアミノで置換されたメチルで置換されたインドリルである 〕か、または、 14)式 の化合物またはその塩を酸化反応に付して、式の化合物またはその塩を製出する〔上記式中、R1、R2、R3、A、EおよびX は各々上に定義した通りであり、 Ytは、ヒドロキシ置換低級アルキルで置換された縮合複素環基であり、 Yuは、ホルミル置換低級アルキルで置換された縮合複素環基である〕か、また は、 15)式 の化合物またはその塩を脱エステル反応に付して、式 の化合物またはその塩を製出する〔上記式中、A、EおよびXは各々上に定義し た通りであり、 R1 aは、エステル化されたカルボキシもしくはエステル化されたカルボキシ置換 低級アルコキシで置換されたアリールであり、 R1 bは、カルボキシもしくはカルボキシ置換低級アルコキシで置換されたアリー ルであり、 R2 aは低級アルキルであり、 R3 aは水素または低級アルコキシであり、 Yvは、低級アルキルもしくは保護されたアミノ低級アルキルで置換されていて もよいベンゾイミダゾリルである〕か、または、 16)式 の化合物またはその塩を、アリールもしくは置換アリールで置換されたメチルの 脱離反応に付して、式 の化合物またはその塩を製出する〔上記式中、R2 a、R3 a、A、E、XおよびY は各々上に定義した通りであり、 R1 cは置換または無置換アリールで置換されたメトキシで置換されているアリー ルであり、 R1 dヒドロキシで置換されたアリールである〕か、または、 17)式の化合物またはそのカルボキシ基における反応性誘導体もしくはそれらの塩をア ミンまたはその塩と反応させて、式 の化合物またはその塩を製出する〔上記式中、R1 b、R2 a、R3 a、A、E、Xお よびYvは各々上に定義した通りであり、 R1 eは、N−保護されたピペラジニルカルボニル、オキソピペリジニルカルボニ ル、カルバモイル、低級アルキルカルバモイル、低級アルキルアミノカルバモイ ルもしくは低級アルキルアミノ低級アルキル(N−低級アルキル)カルバモイル で置換されたアリールであるかまたはN−保護されたピペラジニルカルボニル、 オキソピペリジニルカルボニル、カルバモイル、低級アルキルカルバモイル、低 級アルキルアミノカルバモイルもしくは低級アルキルアミノ低級アルキル(N− 低級アルキル)カルバモイルで置換された低級アルコキシで置換されたアリール である〕か、または、 18)式の化合物またはその塩を還元剤と反応させて、式 の化合物またはその塩を製出する〔上記式中、R2 a、R3 a、A、E、XおよびY vは各々上に定義した通りであり、 R1fはオキソピペリジニルカルボニル置換低級アルコキシで置換されたアリ− ルであり、 R1 gはヒドロキシピペリジニルカルボニル置換低級アルコキシで置換されたアリ ールである〕か、または、 19)式 の化合物またはその塩をアシル化剤と反応させて、式の化合物またはその塩を製出する〔上記式中、R1 d、R2 a、R3 a、A、E、Xお よびYは各々上に定義した通りであり、 R1 hはアシルオキシ置換アリールである〕か、または、 20)式 の化合物またはその塩を式 Z2−R6 (V) の化合物と反応させて、式 の化合物またはその塩を製出する〔上記式中、R1 d、R2 a、R3 a、A、E、Xお よびYは各々上に定義した通りであり、 R1 iは保護されたアミノ置換低級アルコキシで置換されたアリールであり、 R6は保護されたアミノで置換された低級アルキルであり、 Z2は酸残基である〕か、または、 21)式 の化合物またはその塩をN−保護基脱離反応に付して、式 の化合物またはその塩を製出する〔上記式中、R1 i、R2 a、R3 a、A、E、Xお よびYは各々上に定義した通りであり、 R1 jはアミノ置換低級アルコキシで置換されたアリールである〕か、または、 22)式 の化合物またはその塩をアシル化剤と反応させて、式の化合物またはその塩を製出する〔上記式中、R1 jR2 a、R3 a、A、E、Xおよ びYは各々上に定義した通りであり、 R1 kはアシルアミノで置換されたアリールである〕か、または、 23)式 の化合物またはその塩を、還元剤の存在下に、低級アルカナールと反応させて、 式 の化合物またはその塩を製出する〔上記式中、R1 j、R2 a、R3 a、A、E、Xお よびYは各々上に定義した通りであり、 R1 lは低級アルキルアミノで置換されたアリールである〕か、または、 24)式の化合物またはその塩を還元に付して、式 の化合物またはその塩を製出する〔上記式中、R2 a、R3 a、A、E、XおよびY は各々上に定義した通りであり、 R1 mはニトロ置換アリールであり、 R1 nはアミノ置換アリールである〕か、または、 25)式 の化合物またはその塩をアジド化合物と反応させて、式の化合物またはその塩を製出する〔上記式中、R1 n、R2 a、R3 a、A、E、Xお よびYvは各々上に定義した通りであり、 R1 baはカルボキシ置換アリールである〕か、または、 26)式 の化合物またはそのカルボキシ基における反応性誘導体もしくはそれらの塩を還 元剤と反応させて、式 の化合物またはその塩を製出する〔上記式中、R2 a、R3 a、A、E、XおよびY vは各々上に定義した通りであり、 R1 bbはカルボキシ置換低級アルコキシで置換されたアリールであり、 R1 oはヒドロキシメチル置換低級アルコキシで置換されたアリールである〕か、 または、 27)式 の化合物またはその塩をアシル化剤と反応させて、式 の化合物またはその塩を製出する〔上記式中、R2 a、R3 a、A、E、XおよびY vは各々上に定義した通りであり、 R1 pはヒドロキシ置換低級アルコキシで置換されたアリールであり、 R1 qはアシルオキシ置換低級アルコキシで置換されたアリールである〕か、また は、 28)式 の化合物またはその塩をフタルイミドアルカリ金属塩と反応させて、式の化合物またはその塩を製出する〔上記式中、R1 q,R2 a、R3 a、A、E、Xお よびYvは各々上に定義した通りであり、 R1 rはフタルイミド置換低級アルコキシで置換されたアリールである〕か、また は、 29)式 の化合物またはその塩をアミンと反応させて、式 の化合物またはその塩を製出する〔上記式中、R1、R2、R3、A、Eおよび Xは各々上に定義した通りであり、 Ywはハロゲンで置換されたベンゾイミダゾリルであり、 Yxは、N−低級アルキルピペリジル、モルホリノ、低級アルキルアミノ、ジ低 級アルキルアミノピペリジノ、ジ低級アルキルヒドラジノ、アミノ低級アルキル (N−低級アルキル)アミノもしくはジ低級アルキルアミノ低級アルキルアミノ で置換されているベンゾイミダゾリルである〕か、または、 30)式 の化合物またはその塩をN−保護基脱離反応に付して、式 の化合物またはその塩を製出する〔上記式中、R1、R2、R3、A、EおよびX は各々上に定義した通りであり、 YyはN−保護されたピペリジルで置換されたベンゾイミダゾリルであり、 Yzはピペリジルで置換されたベンゾイミダゾリルである〕か、または、 31)式 の化合物またはその塩をヒドロキシルアミンまたはその塩と反応させて、式 の化合物またはその塩を製出する〔上記式中、R1、R2、R3、A、EおよびX は各々上に定義した通りであり、 Y1は、各々にホルミルもしくはシアノ低級アルキルで置換されたべンゾイミダ ゾリルもしくはインドリルであり、 Y2は、各々にヒドロキシイミノメチルもしくはアミノ(ヒドロキシイミノ)低 級アルキルで置換されたベンゾイミダゾリルもしくはインドリルである〕か、ま たは、 32)式 の化合物またはそのカルボキシ基における反応誘導体もしくはそれらの塩を式 H2N−Y (VII) またはその塩と反応させて、式の化合物またはその塩を製出する〔上記式中、R1、R2、R3、XおよびYは各 々上に定義した通りである〕ことを特徴とする前記製造法。 7. 請求の範囲第1項記載の化合物を活性成分とし、これを、製薬上許容され る実質的に無毒性の担体または賦形剤とともに含有する医薬組成物。 8. 医薬として使用するための請求の範囲第1項記載の化合物。 9. 請求の範囲第1項記載の化合物の有効量をヒトまたは動物に投与すること を特徴とする高血圧、心不全、腎不全、浮腫、腹水、バソプレッシン異常分泌症 候群、肝硬変、低ナトリウム血症、低カリウム血症、糖尿病、循環器障害、脳血 管疾患、メニエール症候群または乗物酔いの治療および/または予防方法。 10. ヒトまたは動物における高血圧、心不全、腎不全、浮腫、腹水、バソプ レッシン異常分泌症候群、肝硬変、低ナトリウム血症、低カリウム血症、糖尿 病、循環器障害、脳血管疾患、メニエール症候群または乗物酔いの治療および/ または予防用の薬剤の製造のための請求の範囲第1項記載の化合物の使用。
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AU3953 | 1996-12-02 | ||
AUPO3953A AUPO395396A0 (en) | 1996-12-02 | 1996-12-02 | Benzamide derivatives |
PCT/JP1997/004192 WO1998024771A1 (en) | 1996-12-02 | 1997-11-18 | Benzamide derivatives having a vasopressin antagonistic activity |
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JP2008305474A Pending JP2009143904A (ja) | 1996-12-02 | 2008-10-31 | ベンズアミド誘導体 |
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US (2) | US6207693B1 (ja) |
EP (1) | EP0946519A1 (ja) |
JP (2) | JP4625969B2 (ja) |
AU (2) | AUPO395396A0 (ja) |
WO (1) | WO1998024771A1 (ja) |
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WO1998024771A1 (en) | 1998-06-11 |
US6316482B1 (en) | 2001-11-13 |
AUPO395396A0 (en) | 1997-01-02 |
JP4625969B2 (ja) | 2011-02-02 |
JP2009143904A (ja) | 2009-07-02 |
EP0946519A1 (en) | 1999-10-06 |
AU4967297A (en) | 1998-06-29 |
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