NO744102L

NO744102L -

Info

Publication number: NO744102L
Authority: NO; Norway
Prior art keywords: tetrahydro; azepino; methyl; quinoline; melting point
Prior art date: 1973-11-16

Application number

NO744102A

Other languages

English (en)

Norwegian (no)

Inventor

G Griss

R Hurnaus

W Grell

R Sauter

R Reichl

Original Assignee

Thomae Gmbh Dr K

Priority date

1973-11-16

Filing date

1974-11-14

Publication date

1975-06-16

1973-11-16 Priority claimed from DE2357253A external-priority patent/DE2357253A1/de

1974-09-03 Priority claimed from DE2442097A external-priority patent/DE2442097A1/de

1974-11-14 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1975-06-16 Publication of NO744102L publication Critical patent/NO744102L/no

Links

-1 hydroxy, methoxy, carboxy, cyano, dimethylaminocarbonyl Chemical group 0.000 claims description 93
150000001875 compounds Chemical class 0.000 claims description 73
125000004432 carbon atom Chemical group C* 0.000 claims description 42
239000002253 acid Substances 0.000 claims description 41
239000000203 mixture Substances 0.000 claims description 40
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
238000006243 chemical reaction Methods 0.000 claims description 27
238000000034 method Methods 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
230000010933 acylation Effects 0.000 claims description 15
238000005917 acylation reaction Methods 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 14
125000002252 acyl group Chemical group 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 13
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
230000007062 hydrolysis Effects 0.000 claims description 9
238000006460 hydrolysis reaction Methods 0.000 claims description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
150000007522 mineralic acids Chemical class 0.000 claims description 7
150000007524 organic acids Chemical class 0.000 claims description 7
235000005985 organic acids Nutrition 0.000 claims description 7
230000009467 reduction Effects 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000004423 acyloxy group Chemical group 0.000 claims description 4
150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 4
HFZKWQWSGPACQC-UHFFFAOYSA-N ethyl 5-hydroxy-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound OC1CN(C(=O)OCC)CCC2=C(C)C3=CC=CC=C3N=C21 HFZKWQWSGPACQC-UHFFFAOYSA-N 0.000 claims description 4
150000002828 nitro derivatives Chemical class 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
230000029936 alkylation Effects 0.000 claims description 3
238000005804 alkylation reaction Methods 0.000 claims description 3
150000008064 anhydrides Chemical class 0.000 claims description 3
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 3
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
150000001733 carboxylic acid esters Chemical group 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000012954 diazonium Substances 0.000 claims description 3
150000001989 diazonium salts Chemical class 0.000 claims description 3
150000003248 quinolines Chemical class 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
239000007818 Grignard reagent Substances 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000003368 amide group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
150000001728 carbonyl compounds Chemical class 0.000 claims description 2
125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 2
238000005661 deetherification reaction Methods 0.000 claims description 2
150000004795 grignard reagents Chemical class 0.000 claims description 2
150000002366 halogen compounds Chemical class 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
239000007800 oxidant agent Substances 0.000 claims description 2
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 2
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
238000006886 vinylation reaction Methods 0.000 claims description 2
JTMJBMODXRBQMH-UHFFFAOYSA-N 11-methyl-3-propyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline Chemical compound C1CN(CCC)CCC2=NC3=CC=CC=C3C(C)=C21 JTMJBMODXRBQMH-UHFFFAOYSA-N 0.000 claims 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
125000001246 bromo group Chemical group Br* 0.000 claims 1
230000026030 halogenation Effects 0.000 claims 1
238000005658 halogenation reaction Methods 0.000 claims 1
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims 1
238000006396 nitration reaction Methods 0.000 claims 1
238000002844 melting Methods 0.000 description 310
230000008018 melting Effects 0.000 description 310
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 138
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 104
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 90
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 69
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 49
BTUQCUPQFZHMNS-UHFFFAOYSA-N quinoline;dihydrochloride Chemical compound Cl.Cl.N1=CC=CC2=CC=CC=C21 BTUQCUPQFZHMNS-UHFFFAOYSA-N 0.000 description 47
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 41
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 41
238000000354 decomposition reaction Methods 0.000 description 38
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
235000011121 sodium hydroxide Nutrition 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
239000002904 solvent Substances 0.000 description 28
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
238000009835 boiling Methods 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
239000003480 eluent Substances 0.000 description 23
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 22
239000000243 solution Substances 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
239000000741 silica gel Substances 0.000 description 21
229910002027 silica gel Inorganic materials 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
238000007127 saponification reaction Methods 0.000 description 18
HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
229910052938 sodium sulfate Inorganic materials 0.000 description 16
235000011152 sodium sulphate Nutrition 0.000 description 16
GNLQYCPHDQMWBW-UHFFFAOYSA-N 11-methyl-2,3,4,5-tetrahydro-1h-azepino[4,5-b]quinoline Chemical compound C1CNCCC2=NC3=CC=CC=C3C(C)=C21 GNLQYCPHDQMWBW-UHFFFAOYSA-N 0.000 description 15
238000001816 cooling Methods 0.000 description 14
238000001704 evaporation Methods 0.000 description 13
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 13
238000001035 drying Methods 0.000 description 12
230000008020 evaporation Effects 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
235000019439 ethyl acetate Nutrition 0.000 description 11
238000012360 testing method Methods 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
229960000583 acetic acid Drugs 0.000 description 10
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
125000004494 ethyl ester group Chemical group 0.000 description 9
238000002474 experimental method Methods 0.000 description 9
LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 9
238000000926 separation method Methods 0.000 description 9
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
239000000284 extract Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
241001465754 Metazoa Species 0.000 description 7
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 7
239000012346 acetyl chloride Substances 0.000 description 7
239000005457 ice water Substances 0.000 description 7
239000012280 lithium aluminium hydride Substances 0.000 description 7
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 7
239000012071 phase Substances 0.000 description 7
AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
235000013339 cereals Nutrition 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
239000012452 mother liquor Substances 0.000 description 6
229920000137 polyphosphoric acid Polymers 0.000 description 6
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 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
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 5
238000005903 acid hydrolysis reaction Methods 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
QLKDYXSUIUFQKE-UHFFFAOYSA-N ethyl 11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OCC)CCC2=NC3=CC=CC=C3C(C)=C21 QLKDYXSUIUFQKE-UHFFFAOYSA-N 0.000 description 5
LBTZZOYVNAMIBK-UHFFFAOYSA-N ethyl 5-chloro-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound ClC1CN(C(=O)OCC)CCC2=C(C)C3=CC=CC=C3N=C21 LBTZZOYVNAMIBK-UHFFFAOYSA-N 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
BDTVCRYEYQPEFL-UHFFFAOYSA-N 3-benzyl-2,4,5,6-tetrahydro-1h-azepino[4,5-b]quinolin-11-one Chemical compound C1CC2=NC3=CC=CC=C3C(O)=C2CCN1CC1=CC=CC=C1 BDTVCRYEYQPEFL-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
230000031709 bromination Effects 0.000 description 4
238000005893 bromination reaction Methods 0.000 description 4
238000004821 distillation Methods 0.000 description 4
RBDRWSZNRXQQDQ-UHFFFAOYSA-N ethyl 11-chloro-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCC2=NC3=CC=CC=C3C(Cl)=C21 RBDRWSZNRXQQDQ-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
229940093915 gynecological organic acid Drugs 0.000 description 4
238000002156 mixing Methods 0.000 description 4
230000004899 motility Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
QXXXJLOUYDTIBD-UHFFFAOYSA-N 1-(7-amino-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinolin-3-yl)ethanone Chemical compound C1CN(C(=O)C)CCC2=NC3=C(N)C=CC=C3C(C)=C21 QXXXJLOUYDTIBD-UHFFFAOYSA-N 0.000 description 3
REIIRHCBYXNPSL-UHFFFAOYSA-N 11-methyl-10-nitro-2,3,4,5-tetrahydro-1h-azepino[4,5-b]quinoline Chemical compound C1CNCCC2=NC3=CC=CC([N+]([O-])=O)=C3C(C)=C21 REIIRHCBYXNPSL-UHFFFAOYSA-N 0.000 description 3
XYVNDHODYMIWAP-UHFFFAOYSA-N 11-methyl-2,3,4,5-tetrahydro-1h-azepino[4,3-b]quinoline Chemical compound C1NCCCC2=NC3=CC=CC=C3C(C)=C21 XYVNDHODYMIWAP-UHFFFAOYSA-N 0.000 description 3
LOCOPCXINKNTAS-UHFFFAOYSA-N 11-methyl-7-nitro-2,3,4,5-tetrahydro-1h-azepino[4,5-b]quinoline Chemical compound C1CNCCC2=NC3=C([N+]([O-])=O)C=CC=C3C(C)=C21 LOCOPCXINKNTAS-UHFFFAOYSA-N 0.000 description 3
FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical compound NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 description 3
PYDDQVYLDCQJBB-UHFFFAOYSA-N 2-benzyl-3,4,5,6-tetrahydro-1h-azepino[4,3-b]quinolin-11-one Chemical compound C1CCC2=NC3=CC=CC=C3C(O)=C2CN1CC1=CC=CC=C1 PYDDQVYLDCQJBB-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
241000700159 Rattus Species 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000002026 chloroform extract Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
239000003651 drinking water Substances 0.000 description 3
235000020188 drinking water Nutrition 0.000 description 3
STHLQIWVUUZMSW-UHFFFAOYSA-N ethyl 10-amino-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCC2=NC3=CC=CC(N)=C3C(C)=C21 STHLQIWVUUZMSW-UHFFFAOYSA-N 0.000 description 3
FIRJTUOOBMEYQE-UHFFFAOYSA-N ethyl 11-methoxy-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCC2=NC3=CC=CC=C3C(OC)=C21 FIRJTUOOBMEYQE-UHFFFAOYSA-N 0.000 description 3
CMGDWQFRXJTBKK-UHFFFAOYSA-N ethyl 11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCC2=NC3=CC=CC=C3C(C)=C21 CMGDWQFRXJTBKK-UHFFFAOYSA-N 0.000 description 3
UUQMNWSTCLZRBW-UHFFFAOYSA-N ethyl 11-methyl-1,3,4,5-tetrahydroazepino[4,3-b]quinoline-2-carboxylate;hydrochloride Chemical compound Cl.C1N(C(=O)OCC)CCCC2=NC3=CC=CC=C3C(C)=C21 UUQMNWSTCLZRBW-UHFFFAOYSA-N 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000003921 oil Substances 0.000 description 3
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238000000297 Sandmeyer reaction Methods 0.000 description 1
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241001122767 Theaceae Species 0.000 description 1
YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
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230000002378 acidificating effect Effects 0.000 description 1
239000013543 active substance Substances 0.000 description 1
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238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000003266 anti-allergic effect Effects 0.000 description 1
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239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
239000002830 appetite depressant Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
BBJNAVNUVHGVHG-UHFFFAOYSA-N bis[1-(2-aminophenyl)cyclohexyl]methanone Chemical compound NC1=C(C=CC=C1)C1(CCCCC1)C(=O)C1(CCCCC1)C1=C(C=CC=C1)N BBJNAVNUVHGVHG-UHFFFAOYSA-N 0.000 description 1
244000309464 bull Species 0.000 description 1
NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
244000309466 calf Species 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000008859 change Effects 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
229960003280 cupric chloride Drugs 0.000 description 1
ZLWXRKSLVLKQDF-UHFFFAOYSA-N cyclohexyl 11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1CC2=NC3=CC=CC=C3C(C)=C2CCN1C(=O)OC1CCCCC1 ZLWXRKSLVLKQDF-UHFFFAOYSA-N 0.000 description 1
IWVJLGPDBXCTDA-UHFFFAOYSA-N cyclohexyl carbonochloridate Chemical compound ClC(=O)OC1CCCCC1 IWVJLGPDBXCTDA-UHFFFAOYSA-N 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
APSGYARPKUMBCQ-UHFFFAOYSA-N ethyl 1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OCC)CCC2=CC3=CC=CC=C3N=C21 APSGYARPKUMBCQ-UHFFFAOYSA-N 0.000 description 1
IICPIXRZTXKVMM-UHFFFAOYSA-N ethyl 1,3,4,5-tetrahydroazepino[4,3-b]quinoline-2-carboxylate;hydrochloride Chemical compound Cl.C1N(C(=O)OCC)CCCC2=NC3=CC=CC=C3C=C21 IICPIXRZTXKVMM-UHFFFAOYSA-N 0.000 description 1
IKLKSDDQXRSBTF-UHFFFAOYSA-N ethyl 10-chloro-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCC2=NC3=CC=CC(Cl)=C3C(C)=C21 IKLKSDDQXRSBTF-UHFFFAOYSA-N 0.000 description 1
XEFVPQRYAROVAV-UHFFFAOYSA-N ethyl 10-hydroxy-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate hydrochloride Chemical compound Cl.C(C)OC(=O)N1CCC2=NC=3C=CC=C(C3C(=C2CC1)C)O XEFVPQRYAROVAV-UHFFFAOYSA-N 0.000 description 1
UJTKZXKITVHRRP-UHFFFAOYSA-N ethyl 11-chloro-6-oxido-1,2,4,5-tetrahydroazepino[4,5-b]quinolin-6-ium-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCC2=C(Cl)C3=CC=CC=C3[N+]([O-])=C21 UJTKZXKITVHRRP-UHFFFAOYSA-N 0.000 description 1
KRYMJWPFBKDHGX-UHFFFAOYSA-N ethyl 11-ethyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OCC)CCC2=NC3=CC=CC=C3C(CC)=C21 KRYMJWPFBKDHGX-UHFFFAOYSA-N 0.000 description 1
CGIJTJAXUWEVIQ-UHFFFAOYSA-N ethyl 11-methyl-1,2-dihydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1=CN(C(=O)OCC)CCC2=C(C)C3=CC=CC=C3N=C21 CGIJTJAXUWEVIQ-UHFFFAOYSA-N 0.000 description 1
OQBOLBXQBXSWNQ-UHFFFAOYSA-N ethyl 11-methyl-2,3,4,5-tetrahydro-1h-azepino[4,5-b]quinoline-9-carboxylate;dihydrochloride Chemical compound Cl.Cl.C1CNCCC2=C(C)C3=CC(C(=O)OCC)=CC=C3N=C21 OQBOLBXQBXSWNQ-UHFFFAOYSA-N 0.000 description 1
IWSZIOVWJDZGMV-UHFFFAOYSA-N ethyl 11-methyl-7-nitro-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCC2=NC3=C([N+]([O-])=O)C=CC=C3C(C)=C21 IWSZIOVWJDZGMV-UHFFFAOYSA-N 0.000 description 1
KKOSKRHKXXUNJD-UHFFFAOYSA-N ethyl 11-methyl-7-nitro-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OCC)CCC2=NC3=C([N+]([O-])=O)C=CC=C3C(C)=C21 KKOSKRHKXXUNJD-UHFFFAOYSA-N 0.000 description 1
KHACSSPBQCTDQM-UHFFFAOYSA-N ethyl 11-methyl-9-nitro-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCC2=NC3=CC=C([N+]([O-])=O)C=C3C(C)=C21 KHACSSPBQCTDQM-UHFFFAOYSA-N 0.000 description 1
RYWOCTUTCWLZPL-UHFFFAOYSA-N ethyl 11-methyl-9-nitro-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OCC)CCC2=NC3=CC=C([N+]([O-])=O)C=C3C(C)=C21 RYWOCTUTCWLZPL-UHFFFAOYSA-N 0.000 description 1
LLPGWJYWNJOSHE-UHFFFAOYSA-N ethyl 11-oxo-3,4,5,6-tetrahydro-1h-azepino[4,3-b]quinoline-2-carboxylate Chemical compound C1N(C(=O)OCC)CCCC2=NC3=CC=CC=C3C(O)=C21 LLPGWJYWNJOSHE-UHFFFAOYSA-N 0.000 description 1
QJHWATHJNRHJMD-UHFFFAOYSA-N ethyl 11-phenoxy-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C=12CCN(C(=O)OCC)CCC2=NC2=CC=CC=C2C=1OC1=CC=CC=C1 QJHWATHJNRHJMD-UHFFFAOYSA-N 0.000 description 1
MBVBVGWPHKVFHX-UHFFFAOYSA-N ethyl 11-propyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OCC)CCC2=NC3=CC=CC=C3C(CCC)=C21 MBVBVGWPHKVFHX-UHFFFAOYSA-N 0.000 description 1
CMZYWUPPMFTGOH-UHFFFAOYSA-N ethyl 11-pyrrolidin-1-yl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C=12CCN(C(=O)OCC)CCC2=NC2=CC=CC=C2C=1N1CCCC1 CMZYWUPPMFTGOH-UHFFFAOYSA-N 0.000 description 1
OCPBURJFUBWCDL-UHFFFAOYSA-N ethyl 2-(11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinolin-3-yl)acetate Chemical compound C1CN(CC(=O)OCC)CCC2=NC3=CC=CC=C3C(C)=C21 OCPBURJFUBWCDL-UHFFFAOYSA-N 0.000 description 1
IBYMDUNNUIZOOH-UHFFFAOYSA-N ethyl 3-(11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinolin-3-yl)propanoate Chemical compound C1CN(CCC(=O)OCC)CCC2=NC3=CC=CC=C3C(C)=C21 IBYMDUNNUIZOOH-UHFFFAOYSA-N 0.000 description 1
YZWMBQJLLAPKDF-UHFFFAOYSA-N ethyl 3-(11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinolin-3-yl)propanoate;dihydrochloride Chemical compound Cl.Cl.C1CN(CCC(=O)OCC)CCC2=NC3=CC=CC=C3C(C)=C21 YZWMBQJLLAPKDF-UHFFFAOYSA-N 0.000 description 1
VZUMBPRFDOGPGO-UHFFFAOYSA-N ethyl 4-ethoxy-2,3,6,7-tetrahydroazepine-1-carboxylate Chemical compound CCOC(=O)N1CCC=C(OCC)CC1 VZUMBPRFDOGPGO-UHFFFAOYSA-N 0.000 description 1
ZKVSNWAQTMIHBI-UHFFFAOYSA-N ethyl 5,11-dimethyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.CC1CN(C(=O)OCC)CCC2=C(C)C3=CC=CC=C3N=C21 ZKVSNWAQTMIHBI-UHFFFAOYSA-N 0.000 description 1
PZKWMJABGMSBLV-UHFFFAOYSA-N ethyl 5-(dimethylamino)-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;dihydrochloride Chemical compound Cl.Cl.CN(C)C1CN(C(=O)OCC)CCC2=C(C)C3=CC=CC=C3N=C21 PZKWMJABGMSBLV-UHFFFAOYSA-N 0.000 description 1
UCBVZXLFHFAKOB-UHFFFAOYSA-N ethyl 5-acetyloxy-11-methyl-6-oxido-1,2,4,5-tetrahydroazepino[4,5-b]quinolin-6-ium-3-carboxylate Chemical compound CC(=O)OC1CN(C(=O)OCC)CCC2=C(C)C3=CC=CC=C3[N+]([O-])=C21 UCBVZXLFHFAKOB-UHFFFAOYSA-N 0.000 description 1
GIKGAPMXIOCFPE-UHFFFAOYSA-N ethyl 5-ethoxycarbonyloxy-1,3,4,5-tetrahydroazepino[4,3-b]quinoline-2-carboxylate Chemical compound CCOC(=O)OC1CCN(C(=O)OCC)CC2=CC3=CC=CC=C3N=C12 GIKGAPMXIOCFPE-UHFFFAOYSA-N 0.000 description 1
HFJOORBFXJFLCY-UHFFFAOYSA-N ethyl 5-hydroxy-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.OC1CN(C(=O)OCC)CCC2=C(C)C3=CC=CC=C3N=C21 HFJOORBFXJFLCY-UHFFFAOYSA-N 0.000 description 1
TWUOJXDZYFEAQF-UHFFFAOYSA-N ethyl 5-hydroxy-11-methyl-6-oxido-1,2,4,5-tetrahydroazepino[4,5-b]quinolin-6-ium-3-carboxylate Chemical compound OC1CN(C(=O)OCC)CCC2=C(C)C3=CC=CC=C3[N+]([O-])=C21 TWUOJXDZYFEAQF-UHFFFAOYSA-N 0.000 description 1
CWYGNFPCACGWMN-UHFFFAOYSA-N ethyl 5-methoxy-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound COC1CN(C(=O)OCC)CCC2=C(C)C3=CC=CC=C3N=C21 CWYGNFPCACGWMN-UHFFFAOYSA-N 0.000 description 1
TYCHUJNZELIAKL-UHFFFAOYSA-N ethyl 7-amino-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCC2=NC3=C(N)C=CC=C3C(C)=C21 TYCHUJNZELIAKL-UHFFFAOYSA-N 0.000 description 1
AGMCUJWVDVCVHG-UHFFFAOYSA-N ethyl 7-amino-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OCC)CCC2=NC3=C(N)C=CC=C3C(C)=C21 AGMCUJWVDVCVHG-UHFFFAOYSA-N 0.000 description 1
CNAFQDOBMJSPBS-UHFFFAOYSA-N ethyl 7-chloro-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCC2=NC3=C(Cl)C=CC=C3C(C)=C21 CNAFQDOBMJSPBS-UHFFFAOYSA-N 0.000 description 1
SLVZZQFDADVSOI-UHFFFAOYSA-N ethyl 7-cyano-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OCC)CCC2=NC3=C(C#N)C=CC=C3C(C)=C21 SLVZZQFDADVSOI-UHFFFAOYSA-N 0.000 description 1
RIRFVKTVAGSKNQ-UHFFFAOYSA-N ethyl 7-hydroxy-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCC2=NC3=C(O)C=CC=C3C(C)=C21 RIRFVKTVAGSKNQ-UHFFFAOYSA-N 0.000 description 1
CKVJLUPQCIZOFY-UHFFFAOYSA-N ethyl 7-hydroxy-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OCC)CCC2=NC3=C(O)C=CC=C3C(C)=C21 CKVJLUPQCIZOFY-UHFFFAOYSA-N 0.000 description 1
BJFVGDXEBXJNNY-UHFFFAOYSA-N ethyl 8,11-dimethyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCC2=NC3=CC(C)=CC=C3C(C)=C21 BJFVGDXEBXJNNY-UHFFFAOYSA-N 0.000 description 1
PWHKKJVKABZIHB-UHFFFAOYSA-N ethyl 8-chloro-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OCC)CCC2=NC3=CC(Cl)=CC=C3C(C)=C21 PWHKKJVKABZIHB-UHFFFAOYSA-N 0.000 description 1
KNSODPBMYHRVTO-UHFFFAOYSA-N ethyl 8-hydroxy-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C1CN(C(=O)OCC)CCC2=NC3=CC(O)=CC=C3C(C)=C21 KNSODPBMYHRVTO-UHFFFAOYSA-N 0.000 description 1
GGWOINWYIFLKDP-UHFFFAOYSA-N ethyl 9-acetyl-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OCC)CCC2=NC3=CC=C(C(C)=O)C=C3C(C)=C21 GGWOINWYIFLKDP-UHFFFAOYSA-N 0.000 description 1
HPYKDMSYDAGEIW-UHFFFAOYSA-N ethyl 9-bromo-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OCC)CCC2=NC3=CC=C(Br)C=C3C(C)=C21 HPYKDMSYDAGEIW-UHFFFAOYSA-N 0.000 description 1
QTUALQRNNQWBGA-UHFFFAOYSA-N ethyl 9-chloro-11-phenyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C=12CCN(C(=O)OCC)CCC2=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 QTUALQRNNQWBGA-UHFFFAOYSA-N 0.000 description 1
DSXNFUUTCOHNQX-UHFFFAOYSA-N ethyl 9-hydroxy-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OCC)CCC2=NC3=CC=C(O)C=C3C(C)=C21 DSXNFUUTCOHNQX-UHFFFAOYSA-N 0.000 description 1
SRLSEDZDGNSQGB-UHFFFAOYSA-N ethyl 9-methoxy-11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OCC)CCC2=NC3=CC=C(OC)C=C3C(C)=C21 SRLSEDZDGNSQGB-UHFFFAOYSA-N 0.000 description 1
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
PWOYTBYNBYNZCO-UHFFFAOYSA-N ethyl quinoline-2-carboxylate Chemical compound C1=CC=CC2=NC(C(=O)OCC)=CC=C21 PWOYTBYNBYNZCO-UHFFFAOYSA-N 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000036039 immunity Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
238000004811 liquid chromatography Methods 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 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
239000000463 material Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
KOFCCHYEFONYMY-UHFFFAOYSA-N methyl 11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C1CN(C(=O)OC)CCC2=NC3=CC=CC=C3C(C)=C21 KOFCCHYEFONYMY-UHFFFAOYSA-N 0.000 description 1
ANVRPQCKKYTTDV-UHFFFAOYSA-N methyl 11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate;hydrochloride Chemical compound Cl.C1CN(C(=O)OC)CCC2=NC3=CC=CC=C3C(C)=C21 ANVRPQCKKYTTDV-UHFFFAOYSA-N 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
230000037023 motor activity Effects 0.000 description 1
VYSJWRTVXLVIBC-UHFFFAOYSA-N n,n-dimethyl-2-(11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinolin-3-yl)acetamide;dihydrochloride Chemical compound Cl.Cl.C1CN(CC(=O)N(C)C)CCC2=NC3=CC=CC=C3C(C)=C21 VYSJWRTVXLVIBC-UHFFFAOYSA-N 0.000 description 1
JPXVBYAZFAKTKT-UHFFFAOYSA-N n,n-dimethyl-3-(11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinolin-3-yl)propanamide;dihydrochloride Chemical compound Cl.Cl.C1CN(CCC(=O)N(C)C)CCC2=NC3=CC=CC=C3C(C)=C21 JPXVBYAZFAKTKT-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
CVXGFPPAIUELDV-UHFFFAOYSA-N phenacylazanium;chloride Chemical compound [Cl-].[NH3+]CC(=O)C1=CC=CC=C1 CVXGFPPAIUELDV-UHFFFAOYSA-N 0.000 description 1
WLGAHQJNOLLWFZ-UHFFFAOYSA-N phenyl 11-chloro-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C1CC2=NC3=CC=CC=C3C(Cl)=C2CCN1C(=O)OC1=CC=CC=C1 WLGAHQJNOLLWFZ-UHFFFAOYSA-N 0.000 description 1
YYHQSHMSHWBROX-UHFFFAOYSA-N phenyl 11-chloro-1,3,4,5-tetrahydroazepino[4,3-b]quinoline-2-carboxylate Chemical compound C1CCC2=NC3=CC=CC=C3C(Cl)=C2CN1C(=O)OC1=CC=CC=C1 YYHQSHMSHWBROX-UHFFFAOYSA-N 0.000 description 1
PKCLBNHNWDLKSF-UHFFFAOYSA-N phenyl 11-methyl-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C1CC2=NC3=CC=CC=C3C(C)=C2CCN1C(=O)OC1=CC=CC=C1 PKCLBNHNWDLKSF-UHFFFAOYSA-N 0.000 description 1
FBOXHQPNBXJHQD-UHFFFAOYSA-N phenyl 11-oxo-3,4,5,6-tetrahydro-1h-azepino[4,3-b]quinoline-2-carboxylate Chemical compound C1CCC2=NC3=CC=CC=C3C(O)=C2CN1C(=O)OC1=CC=CC=C1 FBOXHQPNBXJHQD-UHFFFAOYSA-N 0.000 description 1
IRBWDSPQZVGDOH-UHFFFAOYSA-N phenyl 11-phenoxycarbonyloxy-1,2,4,5-tetrahydroazepino[4,5-b]quinoline-3-carboxylate Chemical compound C=12CCN(C(=O)OC=3C=CC=CC=3)CCC2=NC2=CC=CC=C2C=1OC(=O)OC1=CC=CC=C1 IRBWDSPQZVGDOH-UHFFFAOYSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 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
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
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IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
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230000008707 rearrangement Effects 0.000 description 1
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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
239000011734 sodium Substances 0.000 description 1
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235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
235000000891 standard diet Nutrition 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
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UJJDEOLXODWCGK-UHFFFAOYSA-N tert-butyl carbonochloridate Chemical compound CC(C)(C)OC(Cl)=O UJJDEOLXODWCGK-UHFFFAOYSA-N 0.000 description 1
IRFHMTUHTBSEBK-QGZVFWFLSA-N tert-butyl n-[(2s)-2-(2,5-difluorophenyl)-3-quinolin-3-ylpropyl]carbamate Chemical compound C1([C@H](CC=2C=C3C=CC=CC3=NC=2)CNC(=O)OC(C)(C)C)=CC(F)=CC=C1F IRFHMTUHTBSEBK-QGZVFWFLSA-N 0.000 description 1
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
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