KR870000183B1 - 페닐알킬아민의 제조방법 - Google Patents
페닐알킬아민의 제조방법 Download PDFInfo
- Publication number
- KR870000183B1 KR870000183B1 KR1019810004912A KR810004912A KR870000183B1 KR 870000183 B1 KR870000183 B1 KR 870000183B1 KR 1019810004912 A KR1019810004912 A KR 1019810004912A KR 810004912 A KR810004912 A KR 810004912A KR 870000183 B1 KR870000183 B1 KR 870000183B1
- Authority
- KR
- South Korea
- Prior art keywords
- group
- carbon atoms
- phenyl
- amino
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 202
- 238000002360 preparation method Methods 0.000 title description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 30
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 21
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 21
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 20
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 19
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 19
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 278
- -1 phenylalkyl amine Chemical class 0.000 claims description 218
- 125000004432 carbon atom Chemical group C* 0.000 claims description 204
- 125000000217 alkyl group Chemical group 0.000 claims description 113
- 239000012279 sodium borohydride Substances 0.000 claims description 103
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 103
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 82
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 51
- 238000006243 chemical reaction Methods 0.000 claims description 42
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 37
- 125000003277 amino group Chemical group 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 239000011541 reaction mixture Substances 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 239000000460 chlorine Substances 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 125000002252 acyl group Chemical group 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 150000001721 carbon Chemical group 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 210000001072 colon Anatomy 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 18
- 150000004678 hydrides Chemical class 0.000 claims description 17
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 14
- 239000002585 base Substances 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
- 230000001681 protective effect Effects 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 11
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
- 238000009835 boiling Methods 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 238000006722 reduction reaction Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052987 metal hydride Inorganic materials 0.000 claims description 10
- 150000004681 metal hydrides Chemical class 0.000 claims description 10
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 10
- 230000003287 optical effect Effects 0.000 claims description 9
- 241000282472 Canis lupus familiaris Species 0.000 claims description 8
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 6
- 235000019253 formic acid Nutrition 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 claims description 5
- 238000005695 dehalogenation reaction Methods 0.000 claims description 5
- 239000007800 oxidant agent Substances 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 230000002152 alkylating effect Effects 0.000 claims description 4
- 230000029936 alkylation Effects 0.000 claims description 4
- 238000005804 alkylation reaction Methods 0.000 claims description 4
- 230000000269 nucleophilic effect Effects 0.000 claims description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000035479 physiological effects, processes and functions Effects 0.000 claims description 2
- 150000003138 primary alcohols Chemical class 0.000 claims description 2
- 150000003333 secondary alcohols Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims 2
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 150000008051 alkyl sulfates Chemical class 0.000 claims 1
- ZGFPIGGZMWGPPW-UHFFFAOYSA-N formaldehyde;formic acid Chemical compound O=C.OC=O ZGFPIGGZMWGPPW-UHFFFAOYSA-N 0.000 claims 1
- 229910000000 metal hydroxide Inorganic materials 0.000 claims 1
- 150000004692 metal hydroxides Chemical class 0.000 claims 1
- 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 603
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 abstract description 20
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 14
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 101100439664 Arabidopsis thaliana CHR8 gene Proteins 0.000 abstract 1
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 522
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 255
- 238000002329 infrared spectrum Methods 0.000 description 137
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 127
- 238000002211 ultraviolet spectrum Methods 0.000 description 126
- 239000003921 oil Substances 0.000 description 103
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 88
- 238000002844 melting Methods 0.000 description 80
- 230000008018 melting Effects 0.000 description 80
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 69
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 67
- 239000000243 solution Substances 0.000 description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 45
- 125000003118 aryl group Chemical group 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 44
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 38
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 37
- 125000001931 aliphatic group Chemical group 0.000 description 37
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 238000000354 decomposition reaction Methods 0.000 description 25
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 24
- 239000003480 eluent Substances 0.000 description 23
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
- 238000003756 stirring Methods 0.000 description 21
- 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 19
- 239000011734 sodium Substances 0.000 description 19
- 229910052708 sodium Inorganic materials 0.000 description 19
- 239000000203 mixture Substances 0.000 description 18
- 238000001704 evaporation Methods 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 150000003254 radicals Chemical class 0.000 description 16
- 239000000741 silica gel Substances 0.000 description 16
- 229910002027 silica gel Inorganic materials 0.000 description 16
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 229930040373 Paraformaldehyde Natural products 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 12
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 229920002866 paraformaldehyde Polymers 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- ATKJJUFAWYSFID-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-bromoethanone Chemical compound NC1=C(Cl)C=C(C(=O)CBr)C=C1Cl ATKJJUFAWYSFID-UHFFFAOYSA-N 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 11
- 229910021529 ammonia Inorganic materials 0.000 description 11
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 8
- QSUCCPHDCQKGPA-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-chlorophenyl)propylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CNCCCC1=CC=C(C=C1)Cl)O)Cl QSUCCPHDCQKGPA-UHFFFAOYSA-N 0.000 description 7
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- XETXTUWQXVYELX-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=CC=C1)C(C)C)O)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=CC=C1)C(C)C)O)Cl XETXTUWQXVYELX-UHFFFAOYSA-N 0.000 description 7
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 7
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 7
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- JLPKZJDZXIKSCP-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)ethanone Chemical compound CC(=O)C1=CC(Cl)=C(N)C(Cl)=C1 JLPKZJDZXIKSCP-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
- 229910010277 boron hydride Inorganic materials 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 229960004132 diethyl ether Drugs 0.000 description 6
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 6
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- IKYFHRVPKIFGMH-UHFFFAOYSA-N 1-phenoxypropan-2-amine Chemical compound CC(N)COC1=CC=CC=C1 IKYFHRVPKIFGMH-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 230000036772 blood pressure Effects 0.000 description 5
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
- 239000002808 molecular sieve Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- PJKGAXBXMOOWRN-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-fluorophenyl)propylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CNCCCC1=CC=C(C=C1)F)O)Cl PJKGAXBXMOOWRN-UHFFFAOYSA-N 0.000 description 4
- UHXHHIAYNSRNOI-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-methylpropan-1-amine Chemical compound CNCCCC1=CC=C(OC)C=C1 UHXHHIAYNSRNOI-UHFFFAOYSA-N 0.000 description 4
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
- FCVHBUFELUXTLR-UHFFFAOYSA-N [Li].[AlH3] Chemical compound [Li].[AlH3] FCVHBUFELUXTLR-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- FQFXBOPFOMMRTR-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-methoxyphenyl)propylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CNCCCC1=CC=C(C=C1)OC)O)Cl FQFXBOPFOMMRTR-UHFFFAOYSA-N 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- VRLOQSCRPAGPOJ-UHFFFAOYSA-N 2,6-dichloro-4-[2-[methyl-[3-(4-phenylmethoxyphenyl)propyl]amino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)OCC1=CC=CC=C1)C)Cl VRLOQSCRPAGPOJ-UHFFFAOYSA-N 0.000 description 3
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 description 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- QZRIZPHXPSMOTB-UHFFFAOYSA-N 4-[3-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]-methylamino]butyl]phenol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=C(C=C1)O)C)C)O)Cl QZRIZPHXPSMOTB-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CZCSLHYZEQSUNV-UHFFFAOYSA-N [Na].OB(O)O Chemical compound [Na].OB(O)O CZCSLHYZEQSUNV-UHFFFAOYSA-N 0.000 description 3
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 239000013505 freshwater Substances 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 210000005240 left ventricle Anatomy 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229940100595 phenylacetaldehyde Drugs 0.000 description 3
- 229940049953 phenylacetate Drugs 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- IHRGOESZBQNFHV-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-(3-phenylpropylamino)ethanol Chemical compound C1=C(Cl)C(N)=C(Cl)C=C1C(O)CNCCCC1=CC=CC=C1 IHRGOESZBQNFHV-UHFFFAOYSA-N 0.000 description 2
- LSZUQYJZFIPPEM-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-(3-phenylpropylamino)ethanol hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CNCCCC1=CC=CC=C1)O)Cl LSZUQYJZFIPPEM-UHFFFAOYSA-N 0.000 description 2
- SXTLXNHAMYKDLV-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-(4-phenylbutan-2-ylamino)ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CNC(CCC1=CC=CC=C1)C)O)Cl SXTLXNHAMYKDLV-UHFFFAOYSA-N 0.000 description 2
- BTTQPOBBZRHTSK-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[2-(4-methoxyphenyl)sulfinylethyl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCS(=O)C1=CC=C(C=C1)OC)C)O)Cl BTTQPOBBZRHTSK-UHFFFAOYSA-N 0.000 description 2
- BAVNTNTVMYLTOD-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[2-(4-methoxyphenyl)sulfonylethyl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCS(=O)(=O)C1=CC=C(C=C1)OC)C)O)Cl BAVNTNTVMYLTOD-UHFFFAOYSA-N 0.000 description 2
- SJCUUTBHORLQSQ-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-methylsulfanylphenyl)propylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CNCCCC1=CC=C(C=C1)SC)O)Cl SJCUUTBHORLQSQ-UHFFFAOYSA-N 0.000 description 2
- CHQYNJSBKPUEMS-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-methylsulfinylphenyl)propylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CNCCCC1=CC=C(C=C1)S(=O)C)O)Cl CHQYNJSBKPUEMS-UHFFFAOYSA-N 0.000 description 2
- IKCWTZLOUQPHFG-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[ethyl-[3-(4-methoxyphenyl)propyl]amino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)OC)CC)O)Cl IKCWTZLOUQPHFG-UHFFFAOYSA-N 0.000 description 2
- WTQAKCLOBUYQQZ-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[ethyl-[3-(4-phenylmethoxyphenyl)propyl]amino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)OCC1=CC=CC=C1)CC)O)Cl WTQAKCLOBUYQQZ-UHFFFAOYSA-N 0.000 description 2
- YPEDJONAWHXESP-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-bromopropan-1-one Chemical compound CC(Br)C(=O)C1=CC(Cl)=C(N)C(Cl)=C1 YPEDJONAWHXESP-UHFFFAOYSA-N 0.000 description 2
- TYXSUBKQLDEYCV-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)propan-2-one Chemical compound NC1=C(C=C(C=C1Cl)CC(=O)C)Cl TYXSUBKQLDEYCV-UHFFFAOYSA-N 0.000 description 2
- KVTOOEQSGVGZEB-UHFFFAOYSA-N 1-(4-amino-3-chloro-5-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC(F)=C(N)C(Cl)=C1 KVTOOEQSGVGZEB-UHFFFAOYSA-N 0.000 description 2
- WDBUZEIVERAUIA-UHFFFAOYSA-N 2,6-dichloro-4-[2-(3-phenylpropylamino)ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCNCCCC1=CC=CC=C1)Cl WDBUZEIVERAUIA-UHFFFAOYSA-N 0.000 description 2
- RAEWQWKWWDAXGX-UHFFFAOYSA-N 2,6-dichloro-4-[2-(4-phenylbutan-2-ylamino)ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCNC(CCC1=CC=CC=C1)C)Cl RAEWQWKWWDAXGX-UHFFFAOYSA-N 0.000 description 2
- PKYIKZMAAGQBIP-UHFFFAOYSA-N 2,6-dichloro-4-[2-[3-(4-chlorophenyl)propyl-propan-2-ylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)Cl)C(C)C)Cl PKYIKZMAAGQBIP-UHFFFAOYSA-N 0.000 description 2
- MVWWVAXXSKCPIJ-UHFFFAOYSA-N 2,6-dichloro-4-[2-[3-(4-chlorophenyl)propylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCNCCCC1=CC=C(C=C1)Cl)Cl MVWWVAXXSKCPIJ-UHFFFAOYSA-N 0.000 description 2
- QHKTXAPJODWUBR-UHFFFAOYSA-N 2,6-dichloro-4-[2-[3-(4-methoxyphenyl)propyl-methylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)OC)C)Cl QHKTXAPJODWUBR-UHFFFAOYSA-N 0.000 description 2
- ZEUTUBQUVPOVFW-UHFFFAOYSA-N 2,6-dichloro-4-[3-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]propyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCCN(CCC1=CC(=C(C=C1)OC)OC)C)Cl ZEUTUBQUVPOVFW-UHFFFAOYSA-N 0.000 description 2
- OBRJQBPGRPFSNK-UHFFFAOYSA-N 2-(4-amino-3,5-dibromophenyl)-N-[3-(4-methoxyphenyl)propyl]-N-methylacetamide Chemical compound NC1=C(C=C(C=C1Br)CC(=O)N(C)CCCC1=CC=C(C=C1)OC)Br OBRJQBPGRPFSNK-UHFFFAOYSA-N 0.000 description 2
- LNNQFVUXCKAYEU-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-N-(4-phenylbutan-2-yl)-N-propan-2-ylacetamide Chemical compound NC1=C(C=C(C=C1Cl)CC(=O)N(C(CCC1=CC=CC=C1)C)C(C)C)Cl LNNQFVUXCKAYEU-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- STGVIWITSISJFR-UHFFFAOYSA-N 2-amino-3-bromo-5-[2-[4-(4-methoxyphenyl)butyl-methylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)CCN(CCCCC1=CC=C(C=C1)OC)C)Br STGVIWITSISJFR-UHFFFAOYSA-N 0.000 description 2
- MCTWJUNGKOUMKD-UHFFFAOYSA-N 2-amino-3-chloro-5-[2-[3-(4-methoxyphenyl)propyl-methylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)CCN(CCCC1=CC=C(C=C1)OC)C)Cl MCTWJUNGKOUMKD-UHFFFAOYSA-N 0.000 description 2
- WJACVBYLSUCJEP-UHFFFAOYSA-N 2-amino-3-fluoro-5-[1-hydroxy-2-[3-(4-methoxyphenyl)propyl-methylamino]ethyl]benzonitrile Chemical group NC1=C(C=C(C=C1F)C(CN(CCCC1=CC=C(C=C1)OC)C)O)C#N WJACVBYLSUCJEP-UHFFFAOYSA-N 0.000 description 2
- BXQSVGARXQUQMV-UHFFFAOYSA-N 2-amino-3-fluoro-5-[1-hydroxy-2-[3-(4-methoxyphenyl)propylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1F)C(CNCCCC1=CC=C(C=C1)OC)O)C#N BXQSVGARXQUQMV-UHFFFAOYSA-N 0.000 description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 2
- NFYPSCKKUOTMGG-UHFFFAOYSA-N 3-(4-amino-3,5-dibromophenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylpropanamide Chemical compound CN(C(CCC1=CC(=C(C(=C1)Br)N)Br)=O)CCC1=CC(=C(C=C1)OC)OC NFYPSCKKUOTMGG-UHFFFAOYSA-N 0.000 description 2
- NUZDQSUVPDNSSJ-UHFFFAOYSA-N 3-(4-methoxyphenyl)propan-1-amine Chemical compound COC1=CC=C(CCCN)C=C1 NUZDQSUVPDNSSJ-UHFFFAOYSA-N 0.000 description 2
- NMINUJZJBUOQJT-UHFFFAOYSA-N 4-[3-[2-(4-amino-3,5-dichlorophenyl)ethyl-ethylamino]butyl]phenol Chemical compound NC1=C(C=C(C=C1Cl)CCN(C(CCC1=CC=C(C=C1)O)C)CC)Cl NMINUJZJBUOQJT-UHFFFAOYSA-N 0.000 description 2
- AEKIQHFNZLVKIC-UHFFFAOYSA-N 4-[3-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]amino]butyl]phenol Chemical compound NC1=C(C=C(C=C1Cl)C(CNC(CCC1=CC=C(C=C1)O)C)O)Cl AEKIQHFNZLVKIC-UHFFFAOYSA-N 0.000 description 2
- JEIDIUVGCBHAIK-UHFFFAOYSA-N 5-acetyl-2-amino-3-fluorobenzonitrile Chemical compound CC(=O)C1=CC(F)=C(N)C(C#N)=C1 JEIDIUVGCBHAIK-UHFFFAOYSA-N 0.000 description 2
- ZRPZPNYZFSJUPA-UHFFFAOYSA-N ARS-1620 Chemical compound Oc1cccc(F)c1-c1c(Cl)cc2c(ncnc2c1F)N1CCN(CC1)C(=O)C=C ZRPZPNYZFSJUPA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 235000003363 Cornus mas Nutrition 0.000 description 2
- 240000006766 Cornus mas Species 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- ZUYGVZUISYIZIS-UHFFFAOYSA-N N-[2-bromo-4-[1-hydroxy-2-[4-(4-methoxyphenyl)butyl-methylamino]ethyl]phenyl]acetamide Chemical compound N(C(=O)C)C1=C(C=C(C=C1)C(CN(CCCCC1=CC=C(C=C1)OC)C)O)Br ZUYGVZUISYIZIS-UHFFFAOYSA-N 0.000 description 2
- XXYJUIKJLBFBLX-UHFFFAOYSA-N NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)OC)C)O)Cl Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)OC)C)O)Cl XXYJUIKJLBFBLX-UHFFFAOYSA-N 0.000 description 2
- QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 206010003119 arrhythmia Diseases 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- JCLLGHQIWSOORJ-UHFFFAOYSA-N ethyl n-(4-acetyl-2-cyano-6-fluorophenyl)carbamate Chemical compound CCOC(=O)NC1=C(F)C=C(C(C)=O)C=C1C#N JCLLGHQIWSOORJ-UHFFFAOYSA-N 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 229940093915 gynecological organic acid Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 2
- 235000019799 monosodium phosphate Nutrition 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 229960002275 pentobarbital sodium Drugs 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006308 propyl amino group Chemical group 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 229960001367 tartaric acid Drugs 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- UKGJZDSUJSPAJL-YPUOHESYSA-N (e)-n-[(1r)-1-[3,5-difluoro-4-(methanesulfonamido)phenyl]ethyl]-3-[2-propyl-6-(trifluoromethyl)pyridin-3-yl]prop-2-enamide Chemical compound CCCC1=NC(C(F)(F)F)=CC=C1\C=C\C(=O)N[C@H](C)C1=CC(F)=C(NS(C)(=O)=O)C(F)=C1 UKGJZDSUJSPAJL-YPUOHESYSA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
- WJVZBFPUELZLLI-UHFFFAOYSA-N 1-(3,5-dibromo-4-hydroxyphenyl)-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanone Chemical compound BrC=1C=C(C=C(C1O)Br)C(CN(CCCC1=CC=C(C=C1)OC)C)=O WJVZBFPUELZLLI-UHFFFAOYSA-N 0.000 description 1
- RPIUVKDZCDEBEN-UHFFFAOYSA-N 1-(3,5-dichloro-4-hydroxyphenyl)-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanone Chemical compound ClC=1C=C(C=C(C1O)Cl)C(CN(CCCC1=CC=C(C=C1)OC)C)=O RPIUVKDZCDEBEN-UHFFFAOYSA-N 0.000 description 1
- VFVBHOMXAVKWCX-UHFFFAOYSA-N 1-(3-chloro-4-piperidin-1-ylphenyl)-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanone Chemical compound ClC=1C=C(C=CC1N1CCCCC1)C(CN(CCCC1=CC=C(C=C1)OC)C)=O VFVBHOMXAVKWCX-UHFFFAOYSA-N 0.000 description 1
- XJNXBOKLFJICQP-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-(1-phenoxypropan-2-ylamino)ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CNC(COC1=CC=CC=C1)C)O)Cl XJNXBOKLFJICQP-UHFFFAOYSA-N 0.000 description 1
- UDXHFLYTCJYCKG-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-(1-phenoxypropan-2-ylamino)ethanol hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CNC(COC1=CC=CC=C1)C)O)Cl UDXHFLYTCJYCKG-UHFFFAOYSA-N 0.000 description 1
- STCUGYXURBEKGR-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[2-(4-methoxyphenoxy)ethyl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCOC1=CC=C(C=C1)OC)C)O)Cl STCUGYXURBEKGR-UHFFFAOYSA-N 0.000 description 1
- HCKQHSUKHWDOJI-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[2-(4-methoxyphenyl)ethyl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCC1=CC=C(C=C1)OC)C)O)Cl HCKQHSUKHWDOJI-UHFFFAOYSA-N 0.000 description 1
- CAUYJAVDLZZHBV-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[2-(4-methoxyphenyl)ethyl-methylamino]ethanone Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCC1=CC=C(C=C1)OC)C)=O)Cl CAUYJAVDLZZHBV-UHFFFAOYSA-N 0.000 description 1
- XHQVZOMBOLRTCL-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[2-(4-methoxyphenyl)sulfanylethyl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCSC1=CC=C(C=C1)OC)C)O)Cl XHQVZOMBOLRTCL-UHFFFAOYSA-N 0.000 description 1
- HXCUEBDNSYNOTK-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[2-phenylethyl(3-phenylpropyl)amino]ethanol hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=CC=C1)CCC1=CC=CC=C1)O)Cl HXCUEBDNSYNOTK-UHFFFAOYSA-N 0.000 description 1
- KEGKWWXLMBODQS-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(3-methoxyphenyl)propyl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC(=CC=C1)OC)C)O)Cl KEGKWWXLMBODQS-UHFFFAOYSA-N 0.000 description 1
- UTSNCYKYKSWALM-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(3-methoxyphenyl)propylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CNCCCC1=CC(=CC=C1)OC)O)Cl UTSNCYKYKSWALM-UHFFFAOYSA-N 0.000 description 1
- MGGGGXXXUNQUNM-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-chlorophenyl)propyl-(2-phenylethyl)amino]ethanol hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)Cl)CCC1=CC=CC=C1)O)Cl MGGGGXXXUNQUNM-UHFFFAOYSA-N 0.000 description 1
- MVXZWPVXMGCLLB-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-chlorophenyl)propyl-ethylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)Cl)CC)O)Cl MVXZWPVXMGCLLB-UHFFFAOYSA-N 0.000 description 1
- MJCWCSASGLDKCY-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-chlorophenyl)propyl-methylamino]ethanol hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)Cl)C)O)Cl MJCWCSASGLDKCY-UHFFFAOYSA-N 0.000 description 1
- HRPQVFDYMCBMRU-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-chlorophenyl)propyl-propan-2-ylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)Cl)C(C)C)O)Cl HRPQVFDYMCBMRU-UHFFFAOYSA-N 0.000 description 1
- STFDOEGLAOFFBE-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-chlorophenyl)propyl-propylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)Cl)CCC)O)Cl STFDOEGLAOFFBE-UHFFFAOYSA-N 0.000 description 1
- QXYXQLVYLBPSMG-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-chlorophenyl)propylamino]ethanone Chemical compound NC1=C(C=C(C=C1Cl)C(CNCCCC1=CC=C(C=C1)Cl)=O)Cl QXYXQLVYLBPSMG-UHFFFAOYSA-N 0.000 description 1
- WQWIDLDCNRAHKE-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-fluorophenyl)propyl-(2-phenylethyl)amino]ethanol hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)F)CCC1=CC=CC=C1)O)Cl WQWIDLDCNRAHKE-UHFFFAOYSA-N 0.000 description 1
- OUNKJCNTIXOZQK-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-fluorophenyl)propyl-propan-2-ylamino]ethanol hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)F)C(C)C)O)Cl OUNKJCNTIXOZQK-UHFFFAOYSA-N 0.000 description 1
- GBINIHXUIHHNAX-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-hydroxyphenyl)propylamino]ethanone Chemical compound NC1=C(C=C(C=C1Cl)C(CNCCCC1=CC=C(C=C1)O)=O)Cl GBINIHXUIHHNAX-UHFFFAOYSA-N 0.000 description 1
- VYCIQZAYJJNDIQ-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanone Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)OC)C)=O)Cl VYCIQZAYJJNDIQ-UHFFFAOYSA-N 0.000 description 1
- PAJPIAXIVMGNSJ-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-methoxyphenyl)propyl-propan-2-ylamino]ethanone Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)OC)C(C)C)=O)Cl PAJPIAXIVMGNSJ-UHFFFAOYSA-N 0.000 description 1
- OTJXUUHUHRPPKE-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-methoxyphenyl)propyl-propylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)OC)CCC)O)Cl OTJXUUHUHRPPKE-UHFFFAOYSA-N 0.000 description 1
- GYGXZCJTDDFZLV-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-methoxyphenyl)propylamino]ethanone Chemical compound NC1=C(C=C(C=C1Cl)C(CNCCCC1=CC=C(C=C1)OC)=O)Cl GYGXZCJTDDFZLV-UHFFFAOYSA-N 0.000 description 1
- JGVXHGCPFRXZTJ-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-methoxyphenyl)propylamino]propan-1-one Chemical compound NC1=C(C=C(C=C1Cl)C(C(C)NCCCC1=CC=C(C=C1)OC)=O)Cl JGVXHGCPFRXZTJ-UHFFFAOYSA-N 0.000 description 1
- ZYEZTFNHINAJAP-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[3-(4-phenylmethoxyphenyl)propyl-propan-2-ylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)OCC1=CC=CC=C1)C(C)C)O)Cl ZYEZTFNHINAJAP-UHFFFAOYSA-N 0.000 description 1
- LWGDOTLRRLZWCE-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[4-(4-hydroxyphenyl)butan-2-yl-propan-2-ylamino]ethanone Chemical compound NC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=C(C=C1)O)C)C(C)C)=O)Cl LWGDOTLRRLZWCE-UHFFFAOYSA-N 0.000 description 1
- WSSDJNQWCNKNPW-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[4-(4-hydroxyphenyl)butan-2-ylamino]ethanone Chemical compound NC1=C(C=C(C=C1Cl)C(CNC(CCC1=CC=C(C=C1)O)C)=O)Cl WSSDJNQWCNKNPW-UHFFFAOYSA-N 0.000 description 1
- VEEMGDZCYGSHEK-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[4-(4-methoxyphenyl)butan-2-yl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=C(C=C1)OC)C)C)O)Cl VEEMGDZCYGSHEK-UHFFFAOYSA-N 0.000 description 1
- KICBYLLCUXCTHV-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[4-(4-methoxyphenyl)butan-2-ylamino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CNC(CCC1=CC=C(C=C1)OC)C)O)Cl KICBYLLCUXCTHV-UHFFFAOYSA-N 0.000 description 1
- WFTVJYZWQGYYLD-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[4-(4-methoxyphenyl)butan-2-ylamino]ethanone Chemical compound COC1=CC=C(CCC(C)NCC(=O)C2=CC(Cl)=C(N)C(Cl)=C2)C=C1 WFTVJYZWQGYYLD-UHFFFAOYSA-N 0.000 description 1
- BXZQWIFNFQOWGE-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[benzyl(3-phenylpropyl)amino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=CC=C1)CC1=CC=CC=C1)O)Cl BXZQWIFNFQOWGE-UHFFFAOYSA-N 0.000 description 1
- DQXHKZCMMVSWBF-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[benzyl-[3-(4-chlorophenyl)propyl]amino]ethanol;hydrochloride Chemical compound Cl.C1=C(Cl)C(N)=C(Cl)C=C1C(O)CN(CC=1C=CC=CC=1)CCCC1=CC=C(Cl)C=C1 DQXHKZCMMVSWBF-UHFFFAOYSA-N 0.000 description 1
- KEVNWLIYEJFETA-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[benzyl-[3-(4-fluorophenyl)propyl]amino]ethanol;hydrochloride Chemical compound Cl.C1=C(Cl)C(N)=C(Cl)C=C1C(O)CN(CC=1C=CC=CC=1)CCCC1=CC=C(F)C=C1 KEVNWLIYEJFETA-UHFFFAOYSA-N 0.000 description 1
- IIGVGSNTYLJDFW-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[cyclopropyl-[3-(4-methoxyphenyl)propyl]amino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)OC)C1CC1)O)Cl IIGVGSNTYLJDFW-UHFFFAOYSA-N 0.000 description 1
- PAEQEIYXPVDWRI-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[cyclopropyl-[3-(4-methoxyphenyl)propyl]amino]ethanone Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)OC)C1CC1)=O)Cl PAEQEIYXPVDWRI-UHFFFAOYSA-N 0.000 description 1
- INUVCPKHZRYSEF-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[ethyl(3-phenylpropyl)amino]ethanol hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=CC=C1)CC)O)Cl INUVCPKHZRYSEF-UHFFFAOYSA-N 0.000 description 1
- HXACBRDLJNGSBX-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[ethyl(4-phenylbutan-2-yl)amino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=CC=C1)C)CC)O)Cl HXACBRDLJNGSBX-UHFFFAOYSA-N 0.000 description 1
- BAXZVHRUFOWOJB-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[ethyl-[3-(4-methoxyphenyl)propyl]amino]ethanone Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)OC)CC)=O)Cl BAXZVHRUFOWOJB-UHFFFAOYSA-N 0.000 description 1
- COUPYDUEQNNBLK-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[ethyl-[4-(4-hydroxyphenyl)butan-2-yl]amino]ethanone Chemical compound NC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=C(C=C1)O)C)CC)=O)Cl COUPYDUEQNNBLK-UHFFFAOYSA-N 0.000 description 1
- AVBIVZSTBNWDBN-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[methyl(3-phenylpropyl)amino]ethanone Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=CC=C1)C)=O)Cl AVBIVZSTBNWDBN-UHFFFAOYSA-N 0.000 description 1
- AHNAUPXJCJRMBK-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[methyl(3-phenylsulfanylpropyl)amino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCSC1=CC=CC=C1)C)O)Cl AHNAUPXJCJRMBK-UHFFFAOYSA-N 0.000 description 1
- HJWJSTWTNQBBDV-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[methyl(4-phenylbutan-2-yl)amino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=CC=C1)C)C)O)Cl HJWJSTWTNQBBDV-UHFFFAOYSA-N 0.000 description 1
- KVCRTGMPZOTJRL-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[methyl-[3-(4-methylsulfinylphenyl)propyl]amino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)S(=O)C)C)O)Cl KVCRTGMPZOTJRL-UHFFFAOYSA-N 0.000 description 1
- XTLJRHHBJJVBEB-UHFFFAOYSA-N 1-(4-amino-3,5-dichlorophenyl)-2-[methyl-[3-(4-phenylmethoxyphenyl)propyl]amino]ethanol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)OCC1=CC=CC=C1)C)O)Cl XTLJRHHBJJVBEB-UHFFFAOYSA-N 0.000 description 1
- AFETYKUCOCJTRH-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-fluorophenyl)-2-(1-phenoxypropan-2-ylamino)ethanol Chemical compound NC1=C(C=C(C=C1F)C(CNC(COC1=CC=CC=C1)C)O)Br AFETYKUCOCJTRH-UHFFFAOYSA-N 0.000 description 1
- JSBRUZWAWGEJPB-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-fluorophenyl)-2-(1-phenoxypropan-2-ylamino)ethanol dihydrochloride Chemical compound Cl.Cl.NC1=C(C=C(C=C1F)C(CNC(COC1=CC=CC=C1)C)O)Br JSBRUZWAWGEJPB-UHFFFAOYSA-N 0.000 description 1
- VRZMYZQZVPQILD-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-fluorophenyl)-2-[2-(3,4-dimethoxyphenyl)ethylamino]ethanol hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1F)C(CNCCC1=CC(=C(C=C1)OC)OC)O)Br VRZMYZQZVPQILD-UHFFFAOYSA-N 0.000 description 1
- CMGKDQYUMNHVCU-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-fluorophenyl)-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1F)C(CN(CCCC1=CC=C(C=C1)OC)C)O)Br CMGKDQYUMNHVCU-UHFFFAOYSA-N 0.000 description 1
- QBYLWJCVKDWJMH-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-fluorophenyl)-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanone Chemical compound NC1=C(C=C(C=C1F)C(CN(CCCC1=CC=C(C=C1)OC)C)=O)Br QBYLWJCVKDWJMH-UHFFFAOYSA-N 0.000 description 1
- GUESUSZIQYBBAZ-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-fluorophenyl)-2-[ethyl(1-phenoxypropan-2-yl)amino]ethanol Chemical compound NC1=C(C=C(C=C1F)C(CN(C(COC1=CC=CC=C1)C)CC)O)Br GUESUSZIQYBBAZ-UHFFFAOYSA-N 0.000 description 1
- OITHEYAOOVAFHX-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC(F)=C(N)C(Br)=C1 OITHEYAOOVAFHX-UHFFFAOYSA-N 0.000 description 1
- BRAUQVDXTTXAFJ-UHFFFAOYSA-N 1-(4-amino-3-bromophenyl)-2-[2-(4-methoxyphenyl)ethyl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1)C(CN(CCC1=CC=C(C=C1)OC)C)O)Br BRAUQVDXTTXAFJ-UHFFFAOYSA-N 0.000 description 1
- OZGSIWDSOXVSRL-UHFFFAOYSA-N 1-(4-amino-3-bromophenyl)-2-[2-(4-methoxyphenyl)ethyl-methylamino]ethanone Chemical compound NC1=C(C=C(C=C1)C(CN(CCC1=CC=C(C=C1)OC)C)=O)Br OZGSIWDSOXVSRL-UHFFFAOYSA-N 0.000 description 1
- GNPVBFVUYRDQIC-UHFFFAOYSA-N 1-(4-amino-3-bromophenyl)-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1)C(CN(CCCC1=CC=C(C=C1)OC)C)O)Br GNPVBFVUYRDQIC-UHFFFAOYSA-N 0.000 description 1
- JDHSFBRHDMDZLD-UHFFFAOYSA-N 1-(4-amino-3-bromophenyl)-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanone Chemical compound NC1=C(C=C(C=C1)C(CN(CCCC1=CC=C(C=C1)OC)C)=O)Br JDHSFBRHDMDZLD-UHFFFAOYSA-N 0.000 description 1
- GDBGLRPRJTXRKS-UHFFFAOYSA-N 1-(4-amino-3-bromophenyl)-2-[4-(4-methoxyphenyl)butyl-methylamino]ethanone Chemical compound NC1=C(C=C(C=C1)C(CN(CCCCC1=CC=C(C=C1)OC)C)=O)Br GDBGLRPRJTXRKS-UHFFFAOYSA-N 0.000 description 1
- OPYCTKWKALWEOC-UHFFFAOYSA-N 1-(4-amino-3-chloro-5-fluorophenyl)-2-[2-(3,4-dimethoxyphenyl)ethylamino]ethanol hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1F)C(CNCCC1=CC(=C(C=C1)OC)OC)O)Cl OPYCTKWKALWEOC-UHFFFAOYSA-N 0.000 description 1
- RBHSLLVOKNJEQQ-UHFFFAOYSA-N 1-(4-amino-3-chloro-5-fluorophenyl)-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1F)C(CN(CCCC1=CC=C(C=C1)OC)C)O)Cl RBHSLLVOKNJEQQ-UHFFFAOYSA-N 0.000 description 1
- ZSUDCXIGJKFTSF-UHFFFAOYSA-N 1-(4-amino-3-chloro-5-nitrophenyl)-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1[N+](=O)[O-])C(CN(CCCC1=CC=C(C=C1)OC)C)O)Cl ZSUDCXIGJKFTSF-UHFFFAOYSA-N 0.000 description 1
- IXTFNRFUVVNJPB-UHFFFAOYSA-N 1-(4-amino-3-chloro-5-nitrophenyl)-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanone Chemical compound NC1=C(C=C(C=C1[N+](=O)[O-])C(CN(CCCC1=CC=C(C=C1)OC)C)=O)Cl IXTFNRFUVVNJPB-UHFFFAOYSA-N 0.000 description 1
- KCNGMVWIUGHURH-UHFFFAOYSA-N 1-(4-amino-3-chlorophenyl)-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1)C(CN(CCCC1=CC=C(C=C1)OC)C)O)Cl KCNGMVWIUGHURH-UHFFFAOYSA-N 0.000 description 1
- NMZSWDUWLWQNAR-UHFFFAOYSA-N 1-(4-amino-3-chlorophenyl)-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanone Chemical compound NC1=C(C=C(C=C1)C(CN(CCCC1=CC=C(C=C1)OC)C)=O)Cl NMZSWDUWLWQNAR-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- LZPPYLLXPBLTQC-UHFFFAOYSA-N 1-[3,5-dichloro-4-(dimethylamino)phenyl]-2-[3-(4-methoxyphenyl)propyl-methylamino]propan-1-ol Chemical compound CN(C1=C(C=C(C=C1Cl)C(C(N(CCCC1=CC=C(C=C1)OC)C)C)O)Cl)C LZPPYLLXPBLTQC-UHFFFAOYSA-N 0.000 description 1
- HQFPTWKRVSBBEY-UHFFFAOYSA-N 1-[3,5-dichloro-4-(dimethylamino)phenyl]-2-[4-(4-hydroxyphenyl)butan-2-yl-methylamino]ethanone Chemical compound CN(C1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=C(C=C1)O)C)C)=O)Cl)C HQFPTWKRVSBBEY-UHFFFAOYSA-N 0.000 description 1
- QDNJHSGIGNJAFK-UHFFFAOYSA-N 1-[3,5-dichloro-4-(methylamino)phenyl]-2-[4-(4-hydroxyphenyl)butan-2-yl-methylamino]ethanone Chemical compound CNC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=C(C=C1)O)C)C)=O)Cl QDNJHSGIGNJAFK-UHFFFAOYSA-N 0.000 description 1
- HLHGNCNVRPXZNW-UHFFFAOYSA-N 1-[3,5-dichloro-4-(propan-2-ylamino)phenyl]-2-[3-(3-methoxyphenyl)propyl-propan-2-ylamino]ethanol Chemical compound ClC=1C=C(C=C(C=1NC(C)C)Cl)C(CN(CCCC1=CC(=CC=C1)OC)C(C)C)O HLHGNCNVRPXZNW-UHFFFAOYSA-N 0.000 description 1
- AJBBGJZXXCJLJH-UHFFFAOYSA-N 1-[4-amino-3-(trifluoromethyl)phenyl]-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1)C(CN(CCCC1=CC=C(C=C1)OC)C)O)C(F)(F)F AJBBGJZXXCJLJH-UHFFFAOYSA-N 0.000 description 1
- ASIGHHHDHKRARF-UHFFFAOYSA-N 1-[4-amino-3-bromo-5-(trifluoromethyl)phenyl]-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanol Chemical compound COC1=CC=C(CCCN(C)CC(O)C2=CC(Br)=C(N)C(=C2)C(F)(F)F)C=C1 ASIGHHHDHKRARF-UHFFFAOYSA-N 0.000 description 1
- IMKOKMMAIRXSGF-UHFFFAOYSA-N 1-[4-amino-3-bromo-5-(trifluoromethyl)phenyl]-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanone Chemical compound NC1=C(C=C(C=C1C(F)(F)F)C(CN(CCCC1=CC=C(C=C1)OC)C)=O)Br IMKOKMMAIRXSGF-UHFFFAOYSA-N 0.000 description 1
- ONEXPKCVVATFQR-UHFFFAOYSA-N 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-[2-(4-methoxyphenyl)ethyl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1C(F)(F)F)C(CN(CCC1=CC=C(C=C1)OC)C)O)Cl ONEXPKCVVATFQR-UHFFFAOYSA-N 0.000 description 1
- BLJHDGFZYMULPL-UHFFFAOYSA-N 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-[3-(4-methoxyphenyl)propyl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1C(F)(F)F)C(CN(CCCC1=CC=C(C=C1)OC)C)O)Cl BLJHDGFZYMULPL-UHFFFAOYSA-N 0.000 description 1
- COAMPUCDFLOGBC-UHFFFAOYSA-N 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-[4-(4-methoxyphenyl)butyl-methylamino]ethanol Chemical compound NC1=C(C=C(C=C1C(F)(F)F)C(CN(CCCCC1=CC=C(C=C1)OC)C)O)Cl COAMPUCDFLOGBC-UHFFFAOYSA-N 0.000 description 1
- YNXFTZWJVHWKPU-UHFFFAOYSA-N 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-[4-(4-methoxyphenyl)butyl-methylamino]ethanone Chemical compound NC1=C(C=C(C=C1C(F)(F)F)C(CN(CCCCC1=CC=C(C=C1)OC)C)=O)Cl YNXFTZWJVHWKPU-UHFFFAOYSA-N 0.000 description 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 1
- AILAPNVJXJNZAA-UHFFFAOYSA-N 2,4-dichloro-6-[2-[3-(4-chlorophenyl)propyl-propan-2-ylamino]ethyl]-3-propan-2-ylaniline Chemical compound ClC1=CC=C(C=C1)CCCN(CCC1=C(C(=C(C(=C1)Cl)C(C)C)Cl)N)C(C)C AILAPNVJXJNZAA-UHFFFAOYSA-N 0.000 description 1
- GPARVQOXBOKCTR-UHFFFAOYSA-N 2,6-dibromo-4-[1-hydroxy-2-[3-(4-methoxyphenyl)propyl-methylamino]ethyl]phenol Chemical compound BrC=1C=C(C=C(C1O)Br)C(CN(CCCC1=CC=C(C=C1)OC)C)O GPARVQOXBOKCTR-UHFFFAOYSA-N 0.000 description 1
- WDTVNFUKNPIAEK-UHFFFAOYSA-N 2,6-dibromo-4-[2-[3-(4-methoxyphenyl)propyl-methylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Br)CCN(CCCC1=CC=C(C=C1)OC)C)Br WDTVNFUKNPIAEK-UHFFFAOYSA-N 0.000 description 1
- XOGOCNBVDLUMFU-UHFFFAOYSA-N 2,6-dibromo-4-[2-[4-(4-methoxyphenyl)butyl-methylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Br)CCN(CCCCC1=CC=C(C=C1)OC)C)Br XOGOCNBVDLUMFU-UHFFFAOYSA-N 0.000 description 1
- KZLPDABJXVIPJU-UHFFFAOYSA-N 2,6-dichloro-4-[1-hydroxy-2-[3-(4-methoxyphenyl)propyl-methylamino]ethyl]phenol Chemical compound ClC=1C=C(C=C(C1O)Cl)C(CN(CCCC1=CC=C(C=C1)OC)C)O KZLPDABJXVIPJU-UHFFFAOYSA-N 0.000 description 1
- ASQAKUXJBHAALN-UHFFFAOYSA-N 2,6-dichloro-4-[2-(3-phenylpropylamino)ethyl]aniline hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1Cl)CCNCCCC1=CC=CC=C1)Cl ASQAKUXJBHAALN-UHFFFAOYSA-N 0.000 description 1
- QMPATEDLXAXBHS-UHFFFAOYSA-N 2,6-dichloro-4-[2-[2-(4-methoxyphenyl)ethyl-propan-2-ylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCC1=CC=C(C=C1)OC)C(C)C)Cl QMPATEDLXAXBHS-UHFFFAOYSA-N 0.000 description 1
- BPXFGSXZGJIHRF-UHFFFAOYSA-N 2,6-dichloro-4-[2-[3-(3,4-dimethoxyphenyl)propyl-methylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC(=C(C=C1)OC)OC)C)Cl BPXFGSXZGJIHRF-UHFFFAOYSA-N 0.000 description 1
- HPPXAOKIGKXPBT-UHFFFAOYSA-N 2,6-dichloro-4-[2-[3-(4-chlorophenyl)propyl-ethylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)Cl)CC)Cl HPPXAOKIGKXPBT-UHFFFAOYSA-N 0.000 description 1
- HEWGTWNXIWPOMZ-UHFFFAOYSA-N 2,6-dichloro-4-[2-[3-(4-chlorophenyl)propyl-methylamino]ethyl]-N,N-dimethylaniline Chemical compound CN(C1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)Cl)C)Cl)C HEWGTWNXIWPOMZ-UHFFFAOYSA-N 0.000 description 1
- ANSLHCNHGZVLIO-UHFFFAOYSA-N 2,6-dichloro-4-[2-[3-(4-chlorophenyl)propyl-propylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)Cl)CCC)Cl ANSLHCNHGZVLIO-UHFFFAOYSA-N 0.000 description 1
- SBIDMRGYGXMKFI-UHFFFAOYSA-N 2,6-dichloro-4-[2-[3-(4-fluorophenyl)propyl-methylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)F)C)Cl SBIDMRGYGXMKFI-UHFFFAOYSA-N 0.000 description 1
- BKECFASXSVUPLD-UHFFFAOYSA-N 2,6-dichloro-4-[2-[3-(4-fluorophenyl)propylamino]ethyl]aniline Chemical compound NC1=C(Cl)C=C(CCNCCCC2=CC=C(F)C=C2)C=C1Cl BKECFASXSVUPLD-UHFFFAOYSA-N 0.000 description 1
- VMQNPQBTPCLVRK-UHFFFAOYSA-N 2,6-dichloro-4-[2-[3-(4-fluorophenyl)propylamino]ethyl]aniline hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1Cl)CCNCCCC1=CC=C(C=C1)F)Cl VMQNPQBTPCLVRK-UHFFFAOYSA-N 0.000 description 1
- YNKSQCKIZKOLGW-UHFFFAOYSA-N 2,6-dichloro-4-[2-[3-(4-methoxyphenoxy)propyl-methylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCOC1=CC=C(C=C1)OC)C)Cl YNKSQCKIZKOLGW-UHFFFAOYSA-N 0.000 description 1
- ZOMMFCCOZCAPAI-UHFFFAOYSA-N 2,6-dichloro-4-[2-[3-(4-methoxyphenyl)propyl-methylamino]propyl]aniline Chemical compound CC(CC1=CC(=C(C(=C1)Cl)N)Cl)N(CCCC1=CC=C(C=C1)OC)C ZOMMFCCOZCAPAI-UHFFFAOYSA-N 0.000 description 1
- BMQMTMJMUPYGRZ-UHFFFAOYSA-N 2,6-dichloro-4-[2-[3-(4-methoxyphenyl)propyl-propan-2-ylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)OC)C(C)C)Cl BMQMTMJMUPYGRZ-UHFFFAOYSA-N 0.000 description 1
- JVWBZVGIMCOQNW-UHFFFAOYSA-N 2,6-dichloro-4-[2-[3-(4-methoxyphenyl)propyl-propylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)OC)CCC)Cl JVWBZVGIMCOQNW-UHFFFAOYSA-N 0.000 description 1
- DCHLWDKYCUJTLK-UHFFFAOYSA-N 2,6-dichloro-4-[2-[3-chloropropyl(methyl)amino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCCl)C)Cl DCHLWDKYCUJTLK-UHFFFAOYSA-N 0.000 description 1
- LPNSVYYKVZUIFJ-UHFFFAOYSA-N 2,6-dichloro-4-[2-[3-phenylpropyl(propyl)amino]ethyl]aniline hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=CC=C1)CCC)Cl LPNSVYYKVZUIFJ-UHFFFAOYSA-N 0.000 description 1
- OPACMOAEMOOIJU-UHFFFAOYSA-N 2,6-dichloro-4-[2-[4-(4-methoxyphenyl)butyl-methylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCCC1=CC=C(C=C1)OC)C)Cl OPACMOAEMOOIJU-UHFFFAOYSA-N 0.000 description 1
- KMGPHGIQQLNTFH-UHFFFAOYSA-N 2,6-dichloro-4-[2-[4-phenylbutan-2-yl(propan-2-yl)amino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(C(CCC1=CC=CC=C1)C)C(C)C)Cl KMGPHGIQQLNTFH-UHFFFAOYSA-N 0.000 description 1
- JVMXXVDBVHGWFN-UHFFFAOYSA-N 2,6-dichloro-4-[2-[4-phenylbutan-2-yl(propyl)amino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(C(CCC1=CC=CC=C1)C)CCC)Cl JVMXXVDBVHGWFN-UHFFFAOYSA-N 0.000 description 1
- CFXJRKVWEJBGFJ-UHFFFAOYSA-N 2,6-dichloro-4-[2-[cyclopropyl-[3-(4-methoxyphenyl)propyl]amino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)OC)C1CC1)Cl CFXJRKVWEJBGFJ-UHFFFAOYSA-N 0.000 description 1
- FLODVRFRMRWEMV-UHFFFAOYSA-N 2,6-dichloro-4-[2-[ethyl-[3-(4-methoxyphenyl)propyl]amino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)OC)CC)Cl FLODVRFRMRWEMV-UHFFFAOYSA-N 0.000 description 1
- MWMWFWLBWFAKAE-UHFFFAOYSA-N 2,6-dichloro-4-[2-[ethyl-[4-(4-methoxyphenyl)butan-2-yl]amino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(C(CCC1=CC=C(C=C1)OC)C)CC)Cl MWMWFWLBWFAKAE-UHFFFAOYSA-N 0.000 description 1
- UMJWWFYZTQVDTQ-UHFFFAOYSA-N 2,6-dichloro-4-[2-[ethyl-[4-(4-methoxyphenyl)butyl]amino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCCC1=CC=C(C=C1)OC)CC)Cl UMJWWFYZTQVDTQ-UHFFFAOYSA-N 0.000 description 1
- JDJCDYLRYIIHEB-UHFFFAOYSA-N 2,6-dichloro-4-[2-[methyl(3-phenylpropyl)amino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=CC=C1)C)Cl JDJCDYLRYIIHEB-UHFFFAOYSA-N 0.000 description 1
- JIIYHKCMMPHMFJ-UHFFFAOYSA-N 2,6-dichloro-4-[2-[methyl(4-phenylbutan-2-yl)amino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCN(C(CCC1=CC=CC=C1)C)C)Cl JIIYHKCMMPHMFJ-UHFFFAOYSA-N 0.000 description 1
- UGYMIAOKASDSID-UHFFFAOYSA-N 2,6-dichloro-4-[3-[2-(4-methoxyphenyl)ethyl-methylamino]propyl]aniline dihydrochloride Chemical compound Cl.Cl.NC1=C(C=C(C=C1Cl)CCCN(CCC1=CC=C(C=C1)OC)C)Cl UGYMIAOKASDSID-UHFFFAOYSA-N 0.000 description 1
- NTXHOBIJQDBWCV-UHFFFAOYSA-N 2,6-dichloro-4-[3-[3-(4-methoxyphenyl)propyl-methylamino]propyl]-N,N-dimethylaniline Chemical compound CN(C1=C(C=C(C=C1Cl)CCCN(CCCC1=CC=C(C=C1)OC)C)Cl)C NTXHOBIJQDBWCV-UHFFFAOYSA-N 0.000 description 1
- QDIAPAKKHVMMRH-UHFFFAOYSA-N 2,6-dichloro-4-[3-[3-(4-methoxyphenyl)propyl-methylamino]propyl]aniline Chemical compound NC1=C(C=C(C=C1Cl)CCCN(CCCC1=CC=C(C=C1)OC)C)Cl QDIAPAKKHVMMRH-UHFFFAOYSA-N 0.000 description 1
- ALIJLOZUYIHKCI-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-N-(3-phenylpropyl)acetamide Chemical compound NC1=C(C=C(C=C1Cl)CC(=O)NCCCC1=CC=CC=C1)Cl ALIJLOZUYIHKCI-UHFFFAOYSA-N 0.000 description 1
- GTUWORGJYGXLJP-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-N-(4-phenylbutan-2-yl)acetamide Chemical compound NC1=C(C=C(C=C1Cl)CC(=O)NC(CCC1=CC=CC=C1)C)Cl GTUWORGJYGXLJP-UHFFFAOYSA-N 0.000 description 1
- YIZOIQGMMQMZOJ-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-N-[2-(4-methoxyphenyl)ethyl]-N-methylacetamide Chemical compound NC1=C(C=C(C=C1Cl)CC(=O)N(C)CCC1=CC=C(C=C1)OC)Cl YIZOIQGMMQMZOJ-UHFFFAOYSA-N 0.000 description 1
- XPJWVXUWICXMTN-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-N-[3-(2-methoxyphenyl)propyl]-N-methylacetamide Chemical compound NC1=C(C=C(C=C1Cl)CC(=O)N(C)CCCC1=C(C=CC=C1)OC)Cl XPJWVXUWICXMTN-UHFFFAOYSA-N 0.000 description 1
- KGKURXGYUQBPDR-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-N-[3-(4-methoxyphenyl)propyl]-N-methylacetamide Chemical compound NC1=C(C=C(C=C1Cl)CC(=O)N(C)CCCC1=CC=C(C=C1)OC)Cl KGKURXGYUQBPDR-UHFFFAOYSA-N 0.000 description 1
- OZOKKWASGWPFQA-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-N-[3-(4-methoxyphenyl)propyl]-N-propan-2-ylacetamide Chemical compound NC1=C(C=C(C=C1Cl)CC(=O)N(C(C)C)CCCC1=CC=C(C=C1)OC)Cl OZOKKWASGWPFQA-UHFFFAOYSA-N 0.000 description 1
- NNKWTHCCNHQDOQ-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-N-[3-(4-methoxyphenyl)propyl]-N-propylacetamide Chemical compound NC1=C(C=C(C=C1Cl)CC(=O)N(CCC)CCCC1=CC=C(C=C1)OC)Cl NNKWTHCCNHQDOQ-UHFFFAOYSA-N 0.000 description 1
- MDOQAKZFRDAARG-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-N-[4-(4-methoxyphenyl)butan-2-yl]acetamide Chemical compound NC1=C(C=C(C=C1Cl)CC(=O)NC(CCC1=CC=C(C=C1)OC)C)Cl MDOQAKZFRDAARG-UHFFFAOYSA-N 0.000 description 1
- KSUPQOSLQLOPPN-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-N-[4-(4-methoxyphenyl)butyl]-N-methylacetamide Chemical compound NC1=C(C=C(C=C1Cl)CC(=O)N(C)CCCCC1=CC=C(C=C1)OC)Cl KSUPQOSLQLOPPN-UHFFFAOYSA-N 0.000 description 1
- CRZNEUCVGZBHNR-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-N-cyclopropyl-N-[3-(4-methoxyphenyl)propyl]acetamide Chemical compound NC1=C(C=C(C=C1Cl)CC(=O)N(C1CC1)CCCC1=CC=C(C=C1)OC)Cl CRZNEUCVGZBHNR-UHFFFAOYSA-N 0.000 description 1
- SSLXQLVREABMFE-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-N-ethyl-N-[3-(4-methoxyphenyl)propyl]acetamide Chemical compound NC1=C(C=C(C=C1Cl)CC(=O)N(CC)CCCC1=CC=C(C=C1)OC)Cl SSLXQLVREABMFE-UHFFFAOYSA-N 0.000 description 1
- BHBCMUOQGOHOCM-UHFFFAOYSA-N 2-(4-amino-3,5-dichlorophenyl)-N-methyl-N-[3-(4-phenylmethoxyphenyl)propyl]acetamide Chemical compound NC1=C(C=C(C=C1Cl)CC(=O)N(C)CCCC1=CC=C(C=C1)OCC1=CC=CC=C1)Cl BHBCMUOQGOHOCM-UHFFFAOYSA-N 0.000 description 1
- NCMVIVKFIWIXPR-UHFFFAOYSA-N 2-(4-amino-3-bromophenyl)-N-[2-(4-methoxyphenyl)butyl]-N-methylacetamide Chemical compound NC1=C(C=C(C=C1)CC(=O)N(C)CC(CC)C1=CC=C(C=C1)OC)Br NCMVIVKFIWIXPR-UHFFFAOYSA-N 0.000 description 1
- UPFQEMGQLOWEKJ-UHFFFAOYSA-N 2-(4-amino-3-bromophenyl)-N-[2-(4-methoxyphenyl)ethyl]-N-methylacetamide Chemical compound NC1=C(C=C(C=C1)CC(=O)N(C)CCC1=CC=C(C=C1)OC)Br UPFQEMGQLOWEKJ-UHFFFAOYSA-N 0.000 description 1
- DPMOGNRIDLVJTI-UHFFFAOYSA-N 2-(4-amino-3-fluorophenyl)-N-[3-(4-methoxyphenyl)propyl]-N-methylacetamide Chemical compound NC1=C(C=C(C=C1)CC(=O)N(C)CCCC1=CC=C(C=C1)OC)F DPMOGNRIDLVJTI-UHFFFAOYSA-N 0.000 description 1
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical class NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
- AXYCWOAALRKIQD-UHFFFAOYSA-N 2-amino-3-bromo-5-[1-hydroxy-2-[2-(4-methoxyphenyl)ethyl-methylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)C(CN(CCC1=CC=C(C=C1)OC)C)O)Br AXYCWOAALRKIQD-UHFFFAOYSA-N 0.000 description 1
- XYMBWDGXTFYBRN-UHFFFAOYSA-N 2-amino-3-bromo-5-[1-hydroxy-2-[4-(4-methoxyphenyl)butyl-methylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)C(CN(CCCCC1=CC=C(C=C1)OC)C)O)Br XYMBWDGXTFYBRN-UHFFFAOYSA-N 0.000 description 1
- YZUMIWPWEBWTLN-UHFFFAOYSA-N 2-amino-3-bromo-5-[1-hydroxy-2-[4-(4-methoxyphenyl)butyl-propan-2-ylamino]ethyl]benzonitrile hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1C#N)C(CN(CCCCC1=CC=C(C=C1)OC)C(C)C)O)Br YZUMIWPWEBWTLN-UHFFFAOYSA-N 0.000 description 1
- BAUBMEAKFYMJKN-UHFFFAOYSA-N 2-amino-3-bromo-5-[2-[2-(4-methoxyphenyl)ethyl-methylamino]acetyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)C(CN(CCC1=CC=C(C=C1)OC)C)=O)Br BAUBMEAKFYMJKN-UHFFFAOYSA-N 0.000 description 1
- ZLKKOJSBVLHLGK-UHFFFAOYSA-N 2-amino-3-bromo-5-[2-[4-(4-methoxyphenyl)butyl-methylamino]acetyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)C(CN(CCCCC1=CC=C(C=C1)OC)C)=O)Br ZLKKOJSBVLHLGK-UHFFFAOYSA-N 0.000 description 1
- SSCSHCMXMFIJRL-UHFFFAOYSA-N 2-amino-3-bromo-5-[2-[4-(4-methoxyphenyl)butyl-propan-2-ylamino]acetyl]benzonitrile Chemical compound COC1=CC=C(CCCCN(CC(=O)C2=CC(Br)=C(N)C(=C2)C#N)C(C)C)C=C1 SSCSHCMXMFIJRL-UHFFFAOYSA-N 0.000 description 1
- CJVSSTWLZPSLNF-UHFFFAOYSA-N 2-amino-3-bromo-5-[2-[4-(4-methoxyphenyl)butyl-propan-2-ylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)CCN(CCCCC1=CC=C(C=C1)OC)C(C)C)Br CJVSSTWLZPSLNF-UHFFFAOYSA-N 0.000 description 1
- YQUZLQRDTDQJID-UHFFFAOYSA-N 2-amino-3-bromo-5-[2-[4-(4-methoxyphenyl)butyl-propylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)CCN(CCCCC1=CC=C(C=C1)OC)CCC)Br YQUZLQRDTDQJID-UHFFFAOYSA-N 0.000 description 1
- IXPRYTKGBXJYDC-UHFFFAOYSA-N 2-amino-3-bromo-5-[2-[ethyl-[4-(4-methoxyphenyl)butyl]amino]acetyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)C(CN(CCCCC1=CC=C(C=C1)OC)CC)=O)Br IXPRYTKGBXJYDC-UHFFFAOYSA-N 0.000 description 1
- XSYYUSNMQNFOJQ-UHFFFAOYSA-N 2-amino-3-bromo-5-[2-[ethyl-[4-(4-methoxyphenyl)butyl]amino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)CCN(CCCCC1=CC=C(C=C1)OC)CC)Br XSYYUSNMQNFOJQ-UHFFFAOYSA-N 0.000 description 1
- WJDBLNIOXQWSEZ-UHFFFAOYSA-N 2-amino-3-bromo-5-[2-[methyl(4-phenylbutyl)amino]acetyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)C(CN(CCCCC1=CC=CC=C1)C)=O)Br WJDBLNIOXQWSEZ-UHFFFAOYSA-N 0.000 description 1
- CMXHKGLLZAGMLE-UHFFFAOYSA-N 2-amino-3-bromo-5-[2-[methyl(4-phenylbutyl)amino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)CCN(CCCCC1=CC=CC=C1)C)Br CMXHKGLLZAGMLE-UHFFFAOYSA-N 0.000 description 1
- MTVGBVOXZSVFBS-UHFFFAOYSA-N 2-amino-3-chloro-5-[1-hydroxy-2-[2-(4-methoxyphenyl)ethyl-methylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)C(CN(CCC1=CC=C(C=C1)OC)C)O)Cl MTVGBVOXZSVFBS-UHFFFAOYSA-N 0.000 description 1
- SWRFDEMJNOIYGW-UHFFFAOYSA-N 2-amino-3-chloro-5-[1-hydroxy-2-[4-(4-methoxyphenyl)butyl-methylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)C(CN(CCCCC1=CC=C(C=C1)OC)C)O)Cl SWRFDEMJNOIYGW-UHFFFAOYSA-N 0.000 description 1
- ZYWLNOVQHJEKET-UHFFFAOYSA-N 2-amino-3-chloro-5-[2-[2-(4-methoxyphenyl)ethyl-methylamino]acetyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)C(CN(CCC1=CC=C(C=C1)OC)C)=O)Cl ZYWLNOVQHJEKET-UHFFFAOYSA-N 0.000 description 1
- PBWHCIVDSIJSNN-UHFFFAOYSA-N 2-amino-3-chloro-5-[2-[2-(4-methoxyphenyl)ethyl-methylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)CCN(CCC1=CC=C(C=C1)OC)C)Cl PBWHCIVDSIJSNN-UHFFFAOYSA-N 0.000 description 1
- LLXPXBJGEUMHMC-UHFFFAOYSA-N 2-amino-3-chloro-5-[2-[3-(4-methoxyphenyl)propyl-methylamino]acetyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)C(CN(CCCC1=CC=C(C=C1)OC)C)=O)Cl LLXPXBJGEUMHMC-UHFFFAOYSA-N 0.000 description 1
- LPZRXZPGVZAXIA-UHFFFAOYSA-N 2-amino-3-chloro-5-[2-[4-(4-methoxyphenyl)butyl-methylamino]acetyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)C(CN(CCCCC1=CC=C(C=C1)OC)C)=O)Cl LPZRXZPGVZAXIA-UHFFFAOYSA-N 0.000 description 1
- XCQNEEIOKKWZRQ-UHFFFAOYSA-N 2-amino-3-chloro-5-[2-[4-(4-methoxyphenyl)butyl-methylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1C#N)CCN(CCCCC1=CC=C(C=C1)OC)C)Cl XCQNEEIOKKWZRQ-UHFFFAOYSA-N 0.000 description 1
- DXPGTLMFQHQCHA-UHFFFAOYSA-N 2-amino-3-fluoro-5-[1-hydroxy-2-[3-(4-methoxyphenyl)propyl-propan-2-ylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1F)C(CN(CCCC1=CC=C(C=C1)OC)C(C)C)O)C#N DXPGTLMFQHQCHA-UHFFFAOYSA-N 0.000 description 1
- WIAYYZSWMVNOGR-UHFFFAOYSA-N 2-amino-3-fluoro-5-[1-hydroxy-2-[4-(4-hydroxyphenyl)butan-2-ylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1F)C(CNC(CCC1=CC=C(C=C1)O)C)O)C#N WIAYYZSWMVNOGR-UHFFFAOYSA-N 0.000 description 1
- NALUDCROFJAOBJ-UHFFFAOYSA-N 2-amino-3-fluoro-5-[1-hydroxy-2-[4-(4-methoxyphenyl)butan-2-yl-methylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1F)C(CN(C(CCC1=CC=C(C=C1)OC)C)C)O)C#N NALUDCROFJAOBJ-UHFFFAOYSA-N 0.000 description 1
- SPNYJUNNIUHWSY-UHFFFAOYSA-N 2-amino-3-fluoro-5-[1-hydroxy-2-[4-(4-methoxyphenyl)butan-2-ylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1F)C(CNC(CCC1=CC=C(C=C1)OC)C)O)C#N SPNYJUNNIUHWSY-UHFFFAOYSA-N 0.000 description 1
- WGSMEYASWPJLAS-UHFFFAOYSA-N 2-amino-3-fluoro-5-[1-hydroxy-2-[4-(4-methoxyphenyl)butyl-methylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1F)C(CN(CCCCC1=CC=C(C=C1)OC)C)O)C#N WGSMEYASWPJLAS-UHFFFAOYSA-N 0.000 description 1
- BDWOENMKWZGWGI-UHFFFAOYSA-N 2-amino-3-fluoro-5-[2-[2-(4-methoxyphenyl)ethyl-methylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1F)CCN(CCC1=CC=C(C=C1)OC)C)C#N BDWOENMKWZGWGI-UHFFFAOYSA-N 0.000 description 1
- QCFKGABILHXSKR-UHFFFAOYSA-N 2-amino-3-fluoro-5-[2-[3-(4-methoxyphenyl)propyl-methylamino]acetyl]benzonitrile Chemical compound NC1=C(C=C(C=C1F)C(CN(CCCC1=CC=C(C=C1)OC)C)=O)C#N QCFKGABILHXSKR-UHFFFAOYSA-N 0.000 description 1
- YNDAPRKPDFKYQV-UHFFFAOYSA-N 2-amino-3-fluoro-5-[2-[4-(4-hydroxyphenyl)butan-2-ylamino]acetyl]benzonitrile Chemical compound NC1=C(C=C(C=C1F)C(CNC(CCC1=CC=C(C=C1)O)C)=O)C#N YNDAPRKPDFKYQV-UHFFFAOYSA-N 0.000 description 1
- YKLWCIVVIYLCCM-UHFFFAOYSA-N 2-amino-3-fluoro-5-[2-[4-(4-methoxyphenyl)butyl-methylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1F)CCN(CCCCC1=CC=C(C=C1)OC)C)C#N YKLWCIVVIYLCCM-UHFFFAOYSA-N 0.000 description 1
- IYCCRCXKPHFHQJ-UHFFFAOYSA-N 2-amino-5-(2-bromoacetyl)-3-fluorobenzonitrile Chemical compound NC1=C(F)C=C(C(=O)CBr)C=C1C#N IYCCRCXKPHFHQJ-UHFFFAOYSA-N 0.000 description 1
- OMEOQEZIKYQZQQ-UHFFFAOYSA-N 2-amino-5-[1-hydroxy-2-[3-(4-methoxyphenyl)propyl-methylamino]ethyl]benzene-1,3-dicarbonitrile Chemical compound NC1=C(C=C(C=C1C#N)C(CN(CCCC1=CC=C(C=C1)OC)C)O)C#N OMEOQEZIKYQZQQ-UHFFFAOYSA-N 0.000 description 1
- UBXLJHRWMPUCSP-UHFFFAOYSA-N 2-amino-5-[1-hydroxy-2-[3-(4-methoxyphenyl)propyl-methylamino]ethyl]benzonitrile Chemical compound NC1=C(C=C(C=C1)C(CN(CCCC1=CC=C(C=C1)OC)C)O)C#N UBXLJHRWMPUCSP-UHFFFAOYSA-N 0.000 description 1
- DLQVYQMRKTYITE-UHFFFAOYSA-N 2-amino-5-[2-[2-(3,4-dimethoxyphenyl)ethyl-ethylamino]-1-hydroxyethyl]-3-fluorobenzonitrile Chemical compound NC1=C(C=C(C=C1F)C(CN(CCC1=CC(=C(C=C1)OC)OC)CC)O)C#N DLQVYQMRKTYITE-UHFFFAOYSA-N 0.000 description 1
- APJQLTMERNDFFB-UHFFFAOYSA-N 2-amino-5-[2-[2-(3,4-dimethoxyphenyl)ethylamino]-1-hydroxyethyl]-3-fluorobenzonitrile Chemical compound NC1=C(C=C(C=C1F)C(CNCCC1=CC(=C(C=C1)OC)OC)O)C#N APJQLTMERNDFFB-UHFFFAOYSA-N 0.000 description 1
- LGEYOLAFURTIIY-UHFFFAOYSA-N 2-amino-5-[2-[2-(3,4-dimethoxyphenyl)ethylamino]-1-hydroxyethyl]-3-fluorobenzonitrile hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1F)C(CNCCC1=CC(=C(C=C1)OC)OC)O)C#N LGEYOLAFURTIIY-UHFFFAOYSA-N 0.000 description 1
- BVQBTOXTFXZMBZ-UHFFFAOYSA-N 2-amino-5-[2-[3-(4-methoxyphenyl)propyl-methylamino]acetyl]benzene-1,3-dicarbonitrile Chemical compound NC1=C(C=C(C=C1C#N)C(CN(CCCC1=CC=C(C=C1)OC)C)=O)C#N BVQBTOXTFXZMBZ-UHFFFAOYSA-N 0.000 description 1
- LTZUSNFYGUPKGZ-UHFFFAOYSA-N 2-amino-5-[2-[benzyl-[4-(4-methoxyphenyl)butyl]amino]ethyl]-3-bromobenzonitrile Chemical compound NC1=C(C=C(C=C1C#N)CCN(CCCCC1=CC=C(C=C1)OC)CC1=CC=CC=C1)Br LTZUSNFYGUPKGZ-UHFFFAOYSA-N 0.000 description 1
- AHNXSWMCROHWTJ-UHFFFAOYSA-N 2-amino-5-[2-[ethyl-[3-(4-methoxyphenyl)propyl]amino]-1-hydroxyethyl]-3-fluorobenzonitrile hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1F)C(CN(CCCC1=CC=C(C=C1)OC)CC)O)C#N AHNXSWMCROHWTJ-UHFFFAOYSA-N 0.000 description 1
- SNJGFNXLFKBHFJ-UHFFFAOYSA-N 2-bromo-4-[2-[2-(4-methoxyphenyl)ethyl-methylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1)CCN(CCC1=CC=C(C=C1)OC)C)Br SNJGFNXLFKBHFJ-UHFFFAOYSA-N 0.000 description 1
- YYJRAOLOXYISJK-UHFFFAOYSA-N 2-bromo-4-[2-[4-(4-methoxyphenyl)butyl-methylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1)CCN(CCCCC1=CC=C(C=C1)OC)C)Br YYJRAOLOXYISJK-UHFFFAOYSA-N 0.000 description 1
- WJFPUSXYRNYGIX-UHFFFAOYSA-N 2-bromo-4-[3-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]propyl]aniline hydrochloride Chemical compound Cl.NC1=C(C=C(C=C1)CCCN(CCC1=CC(=C(C=C1)OC)OC)C)Br WJFPUSXYRNYGIX-UHFFFAOYSA-N 0.000 description 1
- SFWPPEATWJMVRO-UHFFFAOYSA-N 2-chloro-4-[2-[3-(4-methoxyphenyl)propyl-methylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1)CCN(CCCC1=CC=C(C=C1)OC)C)Cl SFWPPEATWJMVRO-UHFFFAOYSA-N 0.000 description 1
- RBCGRBUKFUXLLF-UHFFFAOYSA-N 2-chloro-4-[2-[methyl-[3-(4-phenylmethoxyphenyl)propyl]amino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1)CCN(CCCC1=CC=C(C=C1)OCC1=CC=CC=C1)C)Cl RBCGRBUKFUXLLF-UHFFFAOYSA-N 0.000 description 1
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-UHFFFAOYSA-N 0.000 description 1
- KXQHXKAMLJGUFU-UHFFFAOYSA-N 2-fluoro-4-[2-[3-(4-methoxyphenyl)propyl-methylamino]ethyl]aniline Chemical compound NC1=C(C=C(C=C1)CCN(CCCC1=CC=C(C=C1)OC)C)F KXQHXKAMLJGUFU-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- MCVSQZGDFGFWTI-UHFFFAOYSA-N 3-(2-methoxyphenyl)-n-methylpropan-1-amine;hydrochloride Chemical compound Cl.CNCCCC1=CC=CC=C1OC MCVSQZGDFGFWTI-UHFFFAOYSA-N 0.000 description 1
- CMIXSQAFEPGHMA-UHFFFAOYSA-N 3-(3-methoxyphenyl)propan-1-amine Chemical compound COC1=CC=CC(CCCN)=C1 CMIXSQAFEPGHMA-UHFFFAOYSA-N 0.000 description 1
- BTAGXIZUJNAHGX-UHFFFAOYSA-N 3-(4-amino-3,5-dibromophenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]propanamide Chemical compound NC1=C(C=C(C=C1Br)CCC(=O)NCCC1=CC(=C(C=C1)OC)OC)Br BTAGXIZUJNAHGX-UHFFFAOYSA-N 0.000 description 1
- MYNOSRDYAOHEQA-UHFFFAOYSA-N 3-(4-amino-3,5-dichlorophenyl)-N-[2-(3,4-dimethoxyphenyl)ethyl]propanamide Chemical compound NC1=C(C=C(C=C1Cl)CCC(=O)NCCC1=CC(=C(C=C1)OC)OC)Cl MYNOSRDYAOHEQA-UHFFFAOYSA-N 0.000 description 1
- AHRUEUQQGORSIK-UHFFFAOYSA-N 3-(4-amino-3,5-dichlorophenyl)-N-[2-(4-methoxyphenyl)ethyl]-N-methylpropanamide Chemical compound NC1=C(C=C(C=C1Cl)CCC(=O)N(CCC1=CC=C(C=C1)OC)C)Cl AHRUEUQQGORSIK-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- ZIIQBRLVKBBHSB-UHFFFAOYSA-N 3-(4-fluorophenyl)-N-methylpropan-1-amine hydrochloride Chemical compound Cl.FC1=CC=C(C=C1)CCCNC ZIIQBRLVKBBHSB-UHFFFAOYSA-N 0.000 description 1
- SBFHTMGYWHTJRO-UHFFFAOYSA-N 3-(4-methoxyphenyl)-n-methylpropan-1-amine;hydrochloride Chemical compound [Cl-].C[NH2+]CCCC1=CC=C(OC)C=C1 SBFHTMGYWHTJRO-UHFFFAOYSA-N 0.000 description 1
- CSGONQJCJBQOLK-UHFFFAOYSA-N 3-(4-methoxyphenyl)propan-1-amine;hydrochloride Chemical compound Cl.COC1=CC=C(CCCN)C=C1 CSGONQJCJBQOLK-UHFFFAOYSA-N 0.000 description 1
- RCJBFPQVDDMGAB-UHFFFAOYSA-N 3-(4-methoxyphenyl)sulfanyl-n-methylpropan-1-amine Chemical compound CNCCCSC1=CC=C(OC)C=C1 RCJBFPQVDDMGAB-UHFFFAOYSA-N 0.000 description 1
- KZVIAMZAFLNPIN-UHFFFAOYSA-N 3-(4-methylsulfanylphenyl)propan-1-amine Chemical compound CSC1=CC=C(CCCN)C=C1 KZVIAMZAFLNPIN-UHFFFAOYSA-N 0.000 description 1
- YGYGASJNJTYNOL-CQSZACIVSA-N 3-[(4r)-2,2-dimethyl-1,1-dioxothian-4-yl]-5-(4-fluorophenyl)-1h-indole-7-carboxamide Chemical compound C1CS(=O)(=O)C(C)(C)C[C@@H]1C1=CNC2=C(C(N)=O)C=C(C=3C=CC(F)=CC=3)C=C12 YGYGASJNJTYNOL-CQSZACIVSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- IXKPAGMZSBOVCY-UHFFFAOYSA-N 3-phenyl-n-propan-2-ylpropan-1-amine;hydrochloride Chemical compound Cl.CC(C)NCCCC1=CC=CC=C1 IXKPAGMZSBOVCY-UHFFFAOYSA-N 0.000 description 1
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 description 1
- 125000005977 3-phenylpropyloxy group Chemical group 0.000 description 1
- MEFFMMAWFPKWRE-UHFFFAOYSA-N 4-(3-amino-3-methylbutyl)phenol Chemical compound CC(C)(N)CCC1=CC=C(O)C=C1 MEFFMMAWFPKWRE-UHFFFAOYSA-N 0.000 description 1
- UJEBDQBUVMAMLE-UHFFFAOYSA-N 4-(4-methoxyphenyl)-n-propan-2-ylbutan-1-amine Chemical compound COC1=CC=C(CCCCNC(C)C)C=C1 UJEBDQBUVMAMLE-UHFFFAOYSA-N 0.000 description 1
- VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
- LBPYKWDSQHEOGQ-UHFFFAOYSA-N 4-[2-[benzyl-[3-(4-chlorophenyl)propyl]amino]ethyl]-2,6-dichloroaniline;hydrochloride Chemical compound Cl.C1=C(Cl)C(N)=C(Cl)C=C1CCN(CC=1C=CC=CC=1)CCCC1=CC=C(Cl)C=C1 LBPYKWDSQHEOGQ-UHFFFAOYSA-N 0.000 description 1
- XMKSSNDPDNTXKQ-UHFFFAOYSA-N 4-[2-[benzyl-[3-(4-fluorophenyl)propyl]amino]ethyl]-2,6-dichloroaniline;hydrochloride Chemical compound Cl.C1=C(Cl)C(N)=C(Cl)C=C1CCN(CC=1C=CC=CC=1)CCCC1=CC=C(F)C=C1 XMKSSNDPDNTXKQ-UHFFFAOYSA-N 0.000 description 1
- CGCZFKSUWKAZJL-UHFFFAOYSA-N 4-[3-(ethylamino)butyl]phenol Chemical compound CCNC(C)CCC1=CC=C(O)C=C1 CGCZFKSUWKAZJL-UHFFFAOYSA-N 0.000 description 1
- BDPFGSXRSXJFMJ-UHFFFAOYSA-N 4-[3-[2-(4-amino-3,5-dichlorophenyl)ethyl-methylamino]-3-methylbutyl]phenol Chemical compound NC1=C(C=C(C=C1Cl)CCN(C(CCC1=CC=C(C=C1)O)(C)C)C)Cl BDPFGSXRSXJFMJ-UHFFFAOYSA-N 0.000 description 1
- RXBRYDRNDJTPRY-UHFFFAOYSA-N 4-[3-[2-(4-amino-3,5-dichlorophenyl)ethyl-methylamino]butyl]phenol Chemical compound NC1=C(C=C(C=C1Cl)CCN(C(CCC1=CC=C(C=C1)O)C)C)Cl RXBRYDRNDJTPRY-UHFFFAOYSA-N 0.000 description 1
- KFXVUGPKRIBSMD-UHFFFAOYSA-N 4-[3-[2-(4-amino-3,5-dichlorophenyl)ethyl-methylamino]propyl]phenol Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)O)C)Cl KFXVUGPKRIBSMD-UHFFFAOYSA-N 0.000 description 1
- HGGSXCGMCNJZRV-UHFFFAOYSA-N 4-[3-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]-ethylamino]propyl]phenol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)O)CC)O)Cl HGGSXCGMCNJZRV-UHFFFAOYSA-N 0.000 description 1
- RYQADANLQRBMTA-UHFFFAOYSA-N 4-[3-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]-methylamino]-3-methylbutyl]phenol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=C(C=C1)O)(C)C)C)O)Cl RYQADANLQRBMTA-UHFFFAOYSA-N 0.000 description 1
- XNDOXCCLVDVAGA-UHFFFAOYSA-N 4-[3-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]-methylamino]propyl]phenol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)O)C)O)Cl XNDOXCCLVDVAGA-UHFFFAOYSA-N 0.000 description 1
- IGTGTWTYUYEELY-UHFFFAOYSA-N 4-[3-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]-propan-2-ylamino]butyl]phenol Chemical compound NC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=C(C=C1)O)C)C(C)C)O)Cl IGTGTWTYUYEELY-UHFFFAOYSA-N 0.000 description 1
- PEGIZGJNCOAUNP-UHFFFAOYSA-N 4-[3-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]amino]-3-methylbutyl]phenol Chemical compound NC1=C(C=C(C=C1Cl)C(CNC(CCC1=CC=C(C=C1)O)(C)C)O)Cl PEGIZGJNCOAUNP-UHFFFAOYSA-N 0.000 description 1
- FAIYNPOXWZFPEV-UHFFFAOYSA-N 4-[3-[[2-(4-amino-3,5-dichlorophenyl)-2-hydroxyethyl]amino]propyl]phenol Chemical compound NC1=C(C=C(C=C1Cl)C(CNCCCC1=CC=C(C=C1)O)O)Cl FAIYNPOXWZFPEV-UHFFFAOYSA-N 0.000 description 1
- DAGNBMGQXBEDIE-UHFFFAOYSA-N 4-[3-[[2-(4-amino-3-chlorophenyl)-2-hydroxyethyl]-ethylamino]propyl]phenol Chemical compound NC1=C(C=C(C=C1)C(CN(CCCC1=CC=C(C=C1)O)CC)O)Cl DAGNBMGQXBEDIE-UHFFFAOYSA-N 0.000 description 1
- YLCBTURSMODBTD-UHFFFAOYSA-N 4-[3-[[2-[3,5-dichloro-4-(dimethylamino)phenyl]-2-hydroxyethyl]-methylamino]butyl]phenol Chemical compound CN(C1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=C(C=C1)O)C)C)O)Cl)C YLCBTURSMODBTD-UHFFFAOYSA-N 0.000 description 1
- YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
- QAMNZGCGXSVYKT-UHFFFAOYSA-N 4-[3-methyl-3-(methylamino)butyl]phenol Chemical compound CC(CCC1=CC=C(C=C1)O)(C)NC QAMNZGCGXSVYKT-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- TVRDURQSCJHQCY-UHFFFAOYSA-N 4-phenyl-n-propan-2-ylbutan-2-amine Chemical compound CC(C)NC(C)CCC1=CC=CC=C1 TVRDURQSCJHQCY-UHFFFAOYSA-N 0.000 description 1
- WECUIGDEWBNQJJ-UHFFFAOYSA-N 4-phenylbutan-2-amine Chemical compound CC(N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 0 BN(*)C(*Cc1cc(*)c(C)c(*)c1)*=C Chemical compound BN(*)C(*Cc1cc(*)c(C)c(*)c1)*=C 0.000 description 1
- HSCBRCLONOCLPU-UHFFFAOYSA-N C(C)OC(=O)NC1=C(C=C(C=C1F)C(CN(CCCC1=CC=C(C=C1)OC)C)O)C#N Chemical compound C(C)OC(=O)NC1=C(C=C(C=C1F)C(CN(CCCC1=CC=C(C=C1)OC)C)O)C#N HSCBRCLONOCLPU-UHFFFAOYSA-N 0.000 description 1
- ZIJCSOPWDDXJLH-UHFFFAOYSA-N C(C)O[AlH]OCC.[Na] Chemical compound C(C)O[AlH]OCC.[Na] ZIJCSOPWDDXJLH-UHFFFAOYSA-N 0.000 description 1
- JAPMJSVZDUYFKL-LWOQYNTDSA-N C1C2[C@@H]1CCC2 Chemical compound C1C2[C@@H]1CCC2 JAPMJSVZDUYFKL-LWOQYNTDSA-N 0.000 description 1
- KOOQJINBDNZUTB-UHFFFAOYSA-N CC(C)CCN(C)C Chemical compound CC(C)CCN(C)C KOOQJINBDNZUTB-UHFFFAOYSA-N 0.000 description 1
- DSKWODILRWNMAG-UHFFFAOYSA-N CC(CCC1=CC=C(C=C1)O)N(C)CC(C2=CC(=C(C(=C2)Cl)NC(=O)C)Cl)O Chemical compound CC(CCC1=CC=C(C=C1)O)N(C)CC(C2=CC(=C(C(=C2)Cl)NC(=O)C)Cl)O DSKWODILRWNMAG-UHFFFAOYSA-N 0.000 description 1
- SUIKABGJDYQJDM-UHFFFAOYSA-N CCOC(=O)OC(CN(C)CCC1=CC=C(C=C1)OC)C2=CC(=C(C(=C2)Cl)N)C#N Chemical compound CCOC(=O)OC(CN(C)CCC1=CC=C(C=C1)OC)C2=CC(=C(C(=C2)Cl)N)C#N SUIKABGJDYQJDM-UHFFFAOYSA-N 0.000 description 1
- BZHPALXWDHBEHA-UHFFFAOYSA-N CNC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=C(C=C1)O)C)C)O)Cl Chemical compound CNC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=C(C=C1)O)C)C)O)Cl BZHPALXWDHBEHA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 1
- JCVOKNPJZLSPDR-UHFFFAOYSA-N Cl.C(C)OC1=CC=C(C=C1)CCCNC Chemical compound Cl.C(C)OC1=CC=C(C=C1)CCCNC JCVOKNPJZLSPDR-UHFFFAOYSA-N 0.000 description 1
- SSGQFLJTVWHFAQ-UHFFFAOYSA-N Cl.CC(C)N(CCCC1=CC=C(F)C=C1)CCC1=CC(Cl)=C(N)C(Cl)=C1 Chemical compound Cl.CC(C)N(CCCC1=CC=C(F)C=C1)CCC1=CC(Cl)=C(N)C(Cl)=C1 SSGQFLJTVWHFAQ-UHFFFAOYSA-N 0.000 description 1
- JLGQDBULZJWVGO-UHFFFAOYSA-N Cl.COC1=CC=C(C=C1)CCCNC(C)C Chemical compound Cl.COC1=CC=C(C=C1)CCCNC(C)C JLGQDBULZJWVGO-UHFFFAOYSA-N 0.000 description 1
- RTZDRJSPDWJQIS-UHFFFAOYSA-N Cl.Cl.NC1=C(C=C(C=C1)CCN(CCCC1=CC=C(C=C1)OC)C)Br Chemical compound Cl.Cl.NC1=C(C=C(C=C1)CCN(CCCC1=CC=C(C=C1)OC)C)Br RTZDRJSPDWJQIS-UHFFFAOYSA-N 0.000 description 1
- RQEHRGQDERHDTC-UHFFFAOYSA-N Cl.Cl.NC1=C(C=C(C=C1F)C(CNC(COC1=CC=CC=C1)C)O)Cl Chemical compound Cl.Cl.NC1=C(C=C(C=C1F)C(CNC(COC1=CC=CC=C1)C)O)Cl RQEHRGQDERHDTC-UHFFFAOYSA-N 0.000 description 1
- HGMGPCNBDNNWAM-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1)CCCNCCC1=CC(=C(C=C1)OC)OC)Br Chemical compound Cl.NC1=C(C=C(C=C1)CCCNCCC1=CC(=C(C=C1)OC)OC)Br HGMGPCNBDNNWAM-UHFFFAOYSA-N 0.000 description 1
- NTYHAZRGFJHCFE-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1C#N)C(CN(CCCCC1=CC=C(C=C1)OC)CC)O)Br Chemical compound Cl.NC1=C(C=C(C=C1C#N)C(CN(CCCCC1=CC=C(C=C1)OC)CC)O)Br NTYHAZRGFJHCFE-UHFFFAOYSA-N 0.000 description 1
- NOSJSXPNLIHCTF-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1C#N)C(CN(CCCCC1=CC=CC=C1)C)O)Br Chemical compound Cl.NC1=C(C=C(C=C1C#N)C(CN(CCCCC1=CC=CC=C1)C)O)Br NOSJSXPNLIHCTF-UHFFFAOYSA-N 0.000 description 1
- YOGRVZLAGGTNJZ-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=CC=C1)C)CCC)O)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=CC=C1)C)CCC)O)Cl YOGRVZLAGGTNJZ-UHFFFAOYSA-N 0.000 description 1
- DMNRMEAYLDXFPK-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)C(CN(C(COC1=CC=CC=C1)C)CC)O)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CN(C(COC1=CC=CC=C1)C)CC)O)Cl DMNRMEAYLDXFPK-UHFFFAOYSA-N 0.000 description 1
- NBMAYMXIBPYKNM-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)F)C)O)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)F)C)O)Cl NBMAYMXIBPYKNM-UHFFFAOYSA-N 0.000 description 1
- FSQOANFUYFVRJC-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)F)CC)O)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)F)CC)O)Cl FSQOANFUYFVRJC-UHFFFAOYSA-N 0.000 description 1
- GQALQRYHEFVNAF-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)F)CCC)O)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)F)CCC)O)Cl GQALQRYHEFVNAF-UHFFFAOYSA-N 0.000 description 1
- MULUBNMTDAWUEJ-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)O)C(C)C)O)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC=C(C=C1)O)C(C)C)O)Cl MULUBNMTDAWUEJ-UHFFFAOYSA-N 0.000 description 1
- XGOGPJWTPROSHI-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)C(CNCCCC1=CC=C(C=C1)F)O)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)C(CNCCCC1=CC=C(C=C1)F)O)Cl XGOGPJWTPROSHI-UHFFFAOYSA-N 0.000 description 1
- RYMYBJMNMRLVQV-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)CCCNCCC1=CC(=C(C=C1)OC)OC)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)CCCNCCC1=CC(=C(C=C1)OC)OC)Cl RYMYBJMNMRLVQV-UHFFFAOYSA-N 0.000 description 1
- JFZMUALABVPZKQ-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)CCN(C(CCC1=CC=CC=C1)C)CC)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)CCN(C(CCC1=CC=CC=C1)C)CC)Cl JFZMUALABVPZKQ-UHFFFAOYSA-N 0.000 description 1
- PSYBWCIEFXUHMR-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)CCN(CCCC1=C(C=CC=C1)OC)C)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)CCN(CCCC1=C(C=CC=C1)OC)C)Cl PSYBWCIEFXUHMR-UHFFFAOYSA-N 0.000 description 1
- YINAIASYLBYVQJ-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)Cl)CCC1=CC=CC=C1)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)Cl)CCC1=CC=CC=C1)Cl YINAIASYLBYVQJ-UHFFFAOYSA-N 0.000 description 1
- FHGVSOZMGRKTHI-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)F)CC)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)F)CC)Cl FHGVSOZMGRKTHI-UHFFFAOYSA-N 0.000 description 1
- PPWPZRTXFGDRJL-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)F)CCC)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=C(C=C1)F)CCC)Cl PPWPZRTXFGDRJL-UHFFFAOYSA-N 0.000 description 1
- RPOICEGXZWLNJD-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=CC=C1)C(C)C)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=CC=C1)C(C)C)Cl RPOICEGXZWLNJD-UHFFFAOYSA-N 0.000 description 1
- VYMLJSMRSRSMLC-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=CC=C1)CC)Cl Chemical compound Cl.NC1=C(C=C(C=C1Cl)CCN(CCCC1=CC=CC=C1)CC)Cl VYMLJSMRSRSMLC-UHFFFAOYSA-N 0.000 description 1
- YPSQXRDGNBUWQT-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1F)C(CN(CCC1=CC=C(C=C1)OC)C)O)C#N Chemical compound Cl.NC1=C(C=C(C=C1F)C(CN(CCC1=CC=C(C=C1)OC)C)O)C#N YPSQXRDGNBUWQT-UHFFFAOYSA-N 0.000 description 1
- RHIPNPKPLYJRJQ-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1F)C(CNC(COC1=CC=CC=C1)C)O)C#N Chemical compound Cl.NC1=C(C=C(C=C1F)C(CNC(COC1=CC=CC=C1)C)O)C#N RHIPNPKPLYJRJQ-UHFFFAOYSA-N 0.000 description 1
- DPUDLHQYFXWHJI-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1F)CCN(CCCC1=CC=C(C=C1)OC)C)C#N Chemical compound Cl.NC1=C(C=C(C=C1F)CCN(CCCC1=CC=C(C=C1)OC)C)C#N DPUDLHQYFXWHJI-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-UHFFFAOYSA-N Cordycepinsaeure Natural products OC1CC(O)(C(O)=O)CC(O)C1O AAWZDTNXLSGCEK-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical group OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 239000001358 L(+)-tartaric acid Substances 0.000 description 1
- 235000011002 L(+)-tartaric acid Nutrition 0.000 description 1
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- QOPONDQBAFSUGE-UHFFFAOYSA-N N-[2,6-dichloro-4-[2-[4-(4-hydroxyphenyl)butan-2-yl-methylamino]acetyl]phenyl]acetamide Chemical compound C(C)(=O)NC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=C(C=C1)O)C)C)=O)Cl QOPONDQBAFSUGE-UHFFFAOYSA-N 0.000 description 1
- PDRQZOSGVYQDKX-UHFFFAOYSA-N N-[2,6-dichloro-4-[3-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]propyl]phenyl]acetamide Chemical compound N(C(=O)C)C1=C(C=C(C=C1Cl)CCCN(CCC1=CC(=C(C=C1)OC)OC)C)Cl PDRQZOSGVYQDKX-UHFFFAOYSA-N 0.000 description 1
- IBKTZDNGCVDRTE-UHFFFAOYSA-N N-[2-(4-amino-3,5-dichlorophenyl)ethyl]-2-(4-methoxyphenyl)-N-propan-2-ylacetamide Chemical compound NC1=C(C=C(C=C1Cl)CCN(C(CC1=CC=C(C=C1)OC)=O)C(C)C)Cl IBKTZDNGCVDRTE-UHFFFAOYSA-N 0.000 description 1
- AVASGABCDVLUCB-UHFFFAOYSA-N N-[2-(4-amino-3,5-dichlorophenyl)ethyl]-4-(4-methoxyphenyl)-N-propan-2-ylbutanamide Chemical compound NC1=C(C=C(C=C1Cl)CCN(C(CCCC1=CC=C(C=C1)OC)=O)C(C)C)Cl AVASGABCDVLUCB-UHFFFAOYSA-N 0.000 description 1
- LKRJCITZVIJSNE-UHFFFAOYSA-N N-[2-(4-amino-3,5-dichlorophenyl)ethyl]-4-(4-methoxyphenyl)butanamide Chemical compound NC1=C(C=C(C=C1Cl)CCNC(CCCC1=CC=C(C=C1)OC)=O)Cl LKRJCITZVIJSNE-UHFFFAOYSA-N 0.000 description 1
- WPUQXLZGZCBRAN-UHFFFAOYSA-N NC1=C(C=C(C=C1)C(CN(CCCC1=CC=C(C=C1)OC)C)O)F Chemical compound NC1=C(C=C(C=C1)C(CN(CCCC1=CC=C(C=C1)OC)C)O)F WPUQXLZGZCBRAN-UHFFFAOYSA-N 0.000 description 1
- SXIBOMOQRKCQCS-UHFFFAOYSA-N NC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=C(C=C1)OC)(C)C)C)O)Cl Chemical compound NC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=C(C=C1)OC)(C)C)C)O)Cl SXIBOMOQRKCQCS-UHFFFAOYSA-N 0.000 description 1
- BJODVOLBARSTFW-UHFFFAOYSA-N NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC(=C(C=C1)OC)OC)C)O)Cl Chemical compound NC1=C(C=C(C=C1Cl)C(CN(CCCC1=CC(=C(C=C1)OC)OC)C)O)Cl BJODVOLBARSTFW-UHFFFAOYSA-N 0.000 description 1
- VTNBGGFJSTUOPK-UHFFFAOYSA-N NC1=C(C=C(C=C1Cl)CC(=O)N(C)CCCSC1=CC=C(C=C1)OC)Cl Chemical compound NC1=C(C=C(C=C1Cl)CC(=O)N(C)CCCSC1=CC=C(C=C1)OC)Cl VTNBGGFJSTUOPK-UHFFFAOYSA-N 0.000 description 1
- GQUVFSQCQQPFIB-UHFFFAOYSA-N NC1=C(C=C(C=C1Cl)CCN(CCC1=CC=C(C=C1)OC)CC)Cl Chemical compound NC1=C(C=C(C=C1Cl)CCN(CCC1=CC=C(C=C1)OC)CC)Cl GQUVFSQCQQPFIB-UHFFFAOYSA-N 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-ZHQZDSKASA-N Quinic acid Natural products O[C@H]1CC(O)(C(O)=O)C[C@H](O)C1O AAWZDTNXLSGCEK-ZHQZDSKASA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
- YGHUFTSFEVPVNX-UHFFFAOYSA-N [1-(4-amino-3-fluorophenyl)-2-(1-phenoxypropan-2-ylamino)ethyl] 4-methylbenzenesulfonate Chemical compound S(=O)(=O)(C1=CC=C(C)C=C1)OC(CNC(COC1=CC=CC=C1)C)C1=CC(=C(C=C1)N)F YGHUFTSFEVPVNX-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- VRAIHTAYLFXSJJ-UHFFFAOYSA-N alumane Chemical compound [AlH3].[AlH3] VRAIHTAYLFXSJJ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 239000002956 ash Substances 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000001595 contractor effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- AINBZKYUNWUTRE-UHFFFAOYSA-N ethanol;propan-2-ol Chemical compound CCO.CC(C)O AINBZKYUNWUTRE-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- CVPAGPZMQOVTGB-UHFFFAOYSA-N ethyl N-[2,6-dichloro-4-[1-hydroxy-2-[4-(4-hydroxyphenyl)butan-2-yl-methylamino]ethyl]phenyl]carbamate Chemical compound C(C)OC(=O)NC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=C(C=C1)O)C)C)O)Cl CVPAGPZMQOVTGB-UHFFFAOYSA-N 0.000 description 1
- KQFOQZLWYRJUDY-UHFFFAOYSA-N ethyl N-[2,6-dichloro-4-[2-[4-(4-hydroxyphenyl)butan-2-yl-methylamino]acetyl]phenyl]carbamate Chemical compound C(C)OC(=O)NC1=C(C=C(C=C1Cl)C(CN(C(CCC1=CC=C(C=C1)O)C)C)=O)Cl KQFOQZLWYRJUDY-UHFFFAOYSA-N 0.000 description 1
- CTUBBWLVBNPZSI-UHFFFAOYSA-N ethyl N-[2-bromo-4-[1-hydroxy-2-[4-(4-methoxyphenyl)butyl-methylamino]ethyl]phenyl]carbamate Chemical compound C(C)OC(=O)NC1=C(C=C(C=C1)C(CN(CCCCC1=CC=C(C=C1)OC)C)O)Br CTUBBWLVBNPZSI-UHFFFAOYSA-N 0.000 description 1
- MBGOAZDBQOWOEA-UHFFFAOYSA-N ethyl N-[2-cyano-6-fluoro-4-[1-hydroxy-2-[3-(4-methoxyphenyl)propylamino]ethyl]phenyl]carbamate Chemical compound C(C)OC(=O)NC1=C(C=C(C=C1F)C(CNCCCC1=CC=C(C=C1)OC)O)C#N MBGOAZDBQOWOEA-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- BLBBMBKUUHYSMI-UHFFFAOYSA-N furan-2,3,4,5-tetrol Chemical compound OC=1OC(O)=C(O)C=1O BLBBMBKUUHYSMI-UHFFFAOYSA-N 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000006629 isopropoxycarbonylamino group Chemical group 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- FYAKVMJQKATGHX-UHFFFAOYSA-N methyl-[3-(4-phenylmethoxyphenyl)propyl]azanium;chloride Chemical compound [Cl-].C1=CC(CCC[NH2+]C)=CC=C1OCC1=CC=CC=C1 FYAKVMJQKATGHX-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- VZUGBLTVBZJZOE-KRWDZBQOSA-N n-[3-[(4s)-2-amino-1,4-dimethyl-6-oxo-5h-pyrimidin-4-yl]phenyl]-5-chloropyrimidine-2-carboxamide Chemical compound N1=C(N)N(C)C(=O)C[C@@]1(C)C1=CC=CC(NC(=O)C=2N=CC(Cl)=CN=2)=C1 VZUGBLTVBZJZOE-KRWDZBQOSA-N 0.000 description 1
- IANVUIHSZXRYAX-UHFFFAOYSA-N n-ethyl-3-phenylpropan-1-amine;hydrochloride Chemical compound Cl.CCNCCCC1=CC=CC=C1 IANVUIHSZXRYAX-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- LZMJNVRJMFMYQS-UHFFFAOYSA-N poseltinib Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC(OC=2C=C(NC(=O)C=C)C=CC=2)=C(OC=C2)C2=N1 LZMJNVRJMFMYQS-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 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
- 238000012360 testing method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B23/00—Record carriers not specific to the method of recording or reproducing; Accessories, e.g. containers, specially adapted for co-operation with the recording or reproducing apparatus ; Intermediate mediums; Apparatus or processes specially adapted for their manufacture
- G11B23/02—Containers; Storing means both adapted to cooperate with the recording or reproducing means
- G11B23/04—Magazines; Cassettes for webs or filaments
- G11B23/08—Magazines; Cassettes for webs or filaments for housing webs or filaments having two distinct ends
- G11B23/087—Magazines; Cassettes for webs or filaments for housing webs or filaments having two distinct ends using two different reels or cores
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B25/00—Apparatus characterised by the shape of record carrier employed but not specific to the method of recording or reproducing, e.g. dictating apparatus; Combinations of such apparatus
- G11B25/06—Apparatus characterised by the shape of record carrier employed but not specific to the method of recording or reproducing, e.g. dictating apparatus; Combinations of such apparatus using web-form record carriers, e.g. tape
- G11B25/066—Apparatus characterised by the shape of record carrier employed but not specific to the method of recording or reproducing, e.g. dictating apparatus; Combinations of such apparatus using web-form record carriers, e.g. tape adapted for use with containers of different sizes or configurations; adaptor devices therefor
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE3046465.4 | 1980-12-10 | ||
DE3046465 | 1980-12-10 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR830007505A KR830007505A (ko) | 1983-10-21 |
KR870000183B1 true KR870000183B1 (ko) | 1987-02-14 |
Family
ID=6118763
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019810004912A KR870000183B1 (ko) | 1980-12-10 | 1981-12-10 | 페닐알킬아민의 제조방법 |
Country Status (32)
Country | Link |
---|---|
JP (1) | JPS57122048A (ja) |
KR (1) | KR870000183B1 (ja) |
AR (1) | AR227802A1 (ja) |
AT (1) | AT379378B (ja) |
AU (1) | AU547655B2 (ja) |
BE (1) | BE891416A (ja) |
CA (1) | CA1202636A (ja) |
CH (1) | CH651541A5 (ja) |
CS (1) | CS229924B2 (ja) |
DD (1) | DD202867A5 (ja) |
DE (1) | DE3146623A1 (ja) |
DK (1) | DK541981A (ja) |
ES (4) | ES8301890A1 (ja) |
FI (1) | FI813934L (ja) |
FR (1) | FR2498596B1 (ja) |
GB (1) | GB2088873B (ja) |
GR (1) | GR77323B (ja) |
HU (1) | HU185676B (ja) |
IE (1) | IE52007B1 (ja) |
IL (1) | IL64498A (ja) |
IT (1) | IT1172129B (ja) |
LU (1) | LU83830A1 (ja) |
NL (1) | NL8105170A (ja) |
NO (1) | NO152649C (ja) |
NZ (1) | NZ199215A (ja) |
PH (1) | PH21599A (ja) |
PL (1) | PL129385B1 (ja) |
PT (1) | PT74112B (ja) |
SE (1) | SE8107387L (ja) |
SU (1) | SU1172449A3 (ja) |
YU (1) | YU290381A (ja) |
ZA (1) | ZA818529B (ja) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4720586A (en) * | 1983-12-06 | 1988-01-19 | Fisons, Plc | Substituted 3,4-dihydroxy-phenylethylamino compounds |
GB8419963D0 (en) * | 1984-08-06 | 1984-09-12 | Lundbeck & Co As H | Intermediate compound and method |
GB8426191D0 (en) * | 1984-10-17 | 1984-11-21 | Glaxo Holdings Ltd | Chemical compounds |
US4943591A (en) * | 1984-10-17 | 1990-07-24 | Glaxo Group Limited | Dichloroaniline derivatives |
GB8603475D0 (en) * | 1986-02-12 | 1986-03-19 | Glaxo Group Ltd | Chemical compounds |
JPS63290852A (ja) * | 1987-02-10 | 1988-11-28 | グラクソ、グループ、リミテッド | 化合物 |
GB8703007D0 (en) * | 1987-02-10 | 1987-03-18 | Glaxo Group Ltd | Chemical compounds |
US4906645A (en) * | 1988-09-12 | 1990-03-06 | Merck & Co., Inc. | Pyridyl aminoethanol compounds with growth promotion and an increase in feed efficiency |
DE4028398A1 (de) * | 1990-09-07 | 1992-03-12 | Thomae Gmbh Dr K | Phenylethanolamine, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
ATE173247T1 (de) * | 1991-10-04 | 1998-11-15 | Taisho Pharmaceutical Co Ltd | Alkoxyphenylalkylaminderivat |
US8349898B2 (en) * | 2008-11-18 | 2013-01-08 | Wisconsin Alumni Research Foundation | Sigma-1 receptor ligands and methods of use |
GB201208775D0 (en) * | 2012-05-18 | 2012-07-04 | Uni I Oslo | Chemical compounds |
US10668030B2 (en) * | 2016-04-21 | 2020-06-02 | University Of Kentucky Research Foundation | Vesicular monoamine transporter-2 ligands and their use in the treatment of psychostimulant abuse |
US11999676B2 (en) | 2016-04-21 | 2024-06-04 | University Of Kentucky Research Foundation | Vesicular monoamine transporter-2 ligands and their use in the treatment of psychostimulant abuse |
WO2023235153A1 (en) * | 2022-05-31 | 2023-12-07 | Corteva Agriscience Llc | Crystalline forms of picolinamide fungicide compound |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1618007A1 (de) * | 1967-05-09 | 1970-10-29 | Thomae Gmbh Dr K | Verfahren zur Herstellung von neuen Amino-monohalogenphenylaethanolaminen |
DE2351281C3 (de) * | 1973-10-12 | 1981-07-30 | Dr. Karl Thomae Gmbh, 7950 Biberach | Aminophenyl-äthanolamin-Derivate, deren Herstellung und Verwendung |
NL176168C (nl) * | 1972-12-18 | 1985-03-01 | Thomae Gmbh Dr K | Werkwijze ter bereiding respectievelijk vervaardiging van een farmaceutisch preparaat en werkwijze ter bereiding van daarbij bruikbare nieuwe gesubstitueerde 1-(4-aminofenyl)-2-amino-ethanol-derivaten die, behalve een analgetische, uterusspasmolytische en anti-spastische werking op de dwarsgestreepte spieren, in het bijzonder een beta2-mimetische en/of beta1-blokkerende werking bezitten. |
GB1523974A (en) * | 1975-02-05 | 1978-09-06 | Yamanouchi Pharma Co Ltd | 4-substituted amino- -aminomethylbenzyl alcohol derivatives |
JPS51125232A (en) * | 1975-02-05 | 1976-11-01 | Yamanouchi Pharmaceut Co Ltd | Process for preparing 4-substituted amido-3,5-dihalogeno-alpha-substituted aminomethylbenzyl alcohols |
FI790459A (fi) * | 1978-02-21 | 1979-08-22 | Sandoz Ag | Nya fenyletylaminer foerfarande foer deras framstaellning och kompositioner innehaollande dem |
CA1120058A (en) * | 1978-07-03 | 1982-03-16 | Jack Mills | Phenethanolamines, formulations and potentiation of oncolytic drugs |
-
1981
- 1981-11-16 NL NL8105170A patent/NL8105170A/nl not_active Application Discontinuation
- 1981-11-25 DE DE19813146623 patent/DE3146623A1/de not_active Withdrawn
- 1981-11-27 SU SU813358171A patent/SU1172449A3/ru active
- 1981-11-30 AT AT0512981A patent/AT379378B/de not_active IP Right Cessation
- 1981-12-02 ES ES507635A patent/ES8301890A1/es not_active Expired
- 1981-12-07 IT IT49853/81A patent/IT1172129B/it active
- 1981-12-07 GR GR66712A patent/GR77323B/el unknown
- 1981-12-07 DD DD81235491A patent/DD202867A5/de unknown
- 1981-12-07 CH CH7800/81A patent/CH651541A5/de not_active IP Right Cessation
- 1981-12-08 DK DK541981A patent/DK541981A/da not_active Application Discontinuation
- 1981-12-08 FI FI813934A patent/FI813934L/fi not_active Application Discontinuation
- 1981-12-09 HU HU813708A patent/HU185676B/hu unknown
- 1981-12-09 NZ NZ199215A patent/NZ199215A/en unknown
- 1981-12-09 IE IE2888/81A patent/IE52007B1/en unknown
- 1981-12-09 AU AU78414/81A patent/AU547655B2/en not_active Ceased
- 1981-12-09 SE SE8107387A patent/SE8107387L/xx not_active Application Discontinuation
- 1981-12-09 GB GB8137051A patent/GB2088873B/en not_active Expired
- 1981-12-09 IL IL64498A patent/IL64498A/xx unknown
- 1981-12-09 BE BE0/206788A patent/BE891416A/fr not_active IP Right Cessation
- 1981-12-09 ZA ZA818529A patent/ZA818529B/xx unknown
- 1981-12-09 NO NO814194A patent/NO152649C/no unknown
- 1981-12-09 PL PL1981234155A patent/PL129385B1/pl unknown
- 1981-12-09 CA CA000391831A patent/CA1202636A/en not_active Expired
- 1981-12-09 JP JP56198337A patent/JPS57122048A/ja active Pending
- 1981-12-10 FR FR8123106A patent/FR2498596B1/fr not_active Expired
- 1981-12-10 LU LU83830A patent/LU83830A1/de unknown
- 1981-12-10 PT PT74112A patent/PT74112B/pt unknown
- 1981-12-10 CS CS819178A patent/CS229924B2/cs unknown
- 1981-12-10 AR AR287754A patent/AR227802A1/es active
- 1981-12-10 PH PH26726A patent/PH21599A/en unknown
- 1981-12-10 KR KR1019810004912A patent/KR870000183B1/ko active IP Right Grant
- 1981-12-10 YU YU02903/81A patent/YU290381A/xx unknown
-
1982
- 1982-06-08 ES ES512915A patent/ES512915A0/es active Granted
- 1982-06-08 ES ES512914A patent/ES8304537A1/es not_active Expired
- 1982-06-08 ES ES512913A patent/ES8304536A1/es not_active Expired
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR870000183B1 (ko) | 페닐알킬아민의 제조방법 | |
DK167009B1 (da) | Cycloalkanooe1,2-baaindolsulfonamider, isomere og fysiologisk acceptable salte deraf, deres fremstilling og anvendelse samt laegemiddel indeholdende dem | |
DE69200685T2 (de) | Benzocyclobutyl- oder Indanyl-Alkyl-Amino-Alkyl substituierte 3-Benzazepin-2-ones, verwendbar in der Behandlung von kardiovaskularen Krankheiten. | |
JP2664503B2 (ja) | 新規アミン、その使用及び製法 | |
IE63816B1 (en) | Novel benzimidazole compounds and their use | |
JP2637737B2 (ja) | 新規な薬剤 | |
FR2562889A1 (fr) | Composes de phenethanolamine. procede pour leur preparation et compositions pharmaceutiques les comprenant | |
US5013760A (en) | Phenylethylamine derivatives and pharmaceutical use | |
CA1268764A (fr) | Derives du dihydro-2,3 benzofuranne, leurs procedes de preparation et les compositions pharmaceutiques les renfermant | |
FR2615512A1 (fr) | Composes de benzamides substitues pharmacologiquement actifs, compositions pharmaceutiques contenant ces composes, et leur procede de preparation | |
HU209481B (en) | Process for the production of substituted 2-amino-1,2,3,4-tetrahydro-naphthalene and 3-aminochromane derivatives | |
TW409113B (en) | Aminotetralin derivatives and compositions and method of use thereof | |
JPS6116394B2 (ja) | ||
PT87503B (pt) | Processo para a preparacao de novos derivados de catecolamina | |
IE50218B1 (en) | Phenylethylamine derivatives,their preparation and use,and formulations and compositions containing the same | |
US4840967A (en) | Carbamate or urea derivatives, their preparation and pharmaceutical compositions comprising them | |
FR2459239A1 (fr) | Nouveaux derives amines du benzothiazole, leur procede de preparation et leur application en therapeutique | |
EP0074873B1 (fr) | Dérivés de phénoxy-3 propanol-2, leur préparation et leur application en thérapeutique | |
AU643099B2 (en) | Pharmaceutically active phenylalkylamino-alkyl compounds | |
US5173502A (en) | Substituted trifluoropropan-1-yl-imidazole alpha 2-receptor anagonists | |
US3997608A (en) | N-substituted-dihydroxyphenethylamines | |
EP0118974B1 (en) | 3,4-dihydroxyphenyl ethyl amine derivatives and pharmaceutical compositions containing them | |
PT99729A (pt) | Processo para a preparacao de derivados do acido hidroxamico que inibem a lipoxigenase | |
KR890000021B1 (ko) | 아릴옥시사이클로알칸올 아미노 알킬렌 아릴케톤 및 이의 제조방법 | |
PT91880B (pt) | Processo para a preparacao de derivados ariloxi-,ariltio-,heteroariloxi- ou heteroariltio-alcenilenicos de aminas e de composicoes farmaceuticas que os contem |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
E701 | Decision to grant or registration of patent right |