JPS6242910B2 - - Google Patents
Info
- Publication number
- JPS6242910B2 JPS6242910B2 JP6769775A JP6769775A JPS6242910B2 JP S6242910 B2 JPS6242910 B2 JP S6242910B2 JP 6769775 A JP6769775 A JP 6769775A JP 6769775 A JP6769775 A JP 6769775A JP S6242910 B2 JPS6242910 B2 JP S6242910B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- chloro
- phthalimidomethyl
- benzophenone
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 67
- -1 pyrrolidino, piperidino, 4-methylpiperazino Chemical group 0.000 claims description 43
- 125000001153 fluoro group Chemical group F* 0.000 claims description 24
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 22
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000003960 organic solvent Substances 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 13
- 125000001246 bromo group Chemical group Br* 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims 3
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- 239000012965 benzophenone Substances 0.000 description 43
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 37
- 238000000034 method Methods 0.000 description 37
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- PAUAJOABXCGLCN-UHFFFAOYSA-N n-(1,3-dioxo-2-benzofuran-4-yl)acetamide Chemical compound CC(=O)NC1=CC=CC2=C1C(=O)OC2=O PAUAJOABXCGLCN-UHFFFAOYSA-N 0.000 description 31
- 239000000725 suspension Substances 0.000 description 29
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 20
- 239000001257 hydrogen Substances 0.000 description 20
- 229910052739 hydrogen Inorganic materials 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 15
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 15
- 239000012346 acetyl chloride Substances 0.000 description 15
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 15
- 150000002431 hydrogen Chemical class 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- FEQAUBVIUZJXKN-UHFFFAOYSA-N propan-2-imine;hydrochloride Chemical compound [Cl-].CC(C)=[NH2+] FEQAUBVIUZJXKN-UHFFFAOYSA-N 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 229940049706 benzodiazepine Drugs 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 7
- 150000001557 benzodiazepines Chemical class 0.000 description 7
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- IFGZUICJFWRSDO-UHFFFAOYSA-N 2-[[4-(2-benzoylphenyl)-5-[(dimethylamino)methyl]-1,2,4-triazol-3-yl]methyl]isoindole-1,3-dione Chemical compound CN(C)CC1=NN=C(CN2C(C3=CC=CC=C3C2=O)=O)N1C1=CC=CC=C1C(=O)C1=CC=CC=C1 IFGZUICJFWRSDO-UHFFFAOYSA-N 0.000 description 4
- LKRNZLYYWVHIFZ-UHFFFAOYSA-N 4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical class C1N=CC2=CC=CC=C2N2C=NN=C12 LKRNZLYYWVHIFZ-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- LVCXDKYVLLYQIH-UHFFFAOYSA-N 1-[8-chloro-6-(2-chlorophenyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]-n,n-dimethylmethanamine Chemical compound C12=CC(Cl)=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1Cl LVCXDKYVLLYQIH-UHFFFAOYSA-N 0.000 description 3
- HSQFDWYDHVWQKZ-UHFFFAOYSA-N 2-[[4-[4-chloro-2-(2-chlorobenzoyl)phenyl]-5-[(dimethylamino)methyl]-1,2,4-triazol-3-yl]methyl]isoindole-1,3-dione Chemical compound CN(C)CC1=NN=C(CN2C(C3=CC=CC=C3C2=O)=O)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl HSQFDWYDHVWQKZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- LGNWUMGEJQAWQD-UHFFFAOYSA-N 1h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound N1=CC2=CC=CC=C2N2CN=NC2=C1 LGNWUMGEJQAWQD-UHFFFAOYSA-N 0.000 description 2
- KROXYHVGFUWTKP-UHFFFAOYSA-N 2-(2-chlorophenyl)quinazoline Chemical compound ClC1=CC=CC=C1C1=NC=C(C=CC=C2)C2=N1 KROXYHVGFUWTKP-UHFFFAOYSA-N 0.000 description 2
- PEKIJLFAGGYWKY-UHFFFAOYSA-N 2-[[4-(2-benzoyl-4-chlorophenyl)-1,2,4-triazol-3-yl]methyl]isoindole-1,3-dione Chemical compound C=1C(Cl)=CC=C(N2C(=NN=C2)CN2C(C3=CC=CC=C3C2=O)=O)C=1C(=O)C1=CC=CC=C1 PEKIJLFAGGYWKY-UHFFFAOYSA-N 0.000 description 2
- KXXARNCTHSKODN-UHFFFAOYSA-N 2-[[4-(2-benzoylphenyl)-1,2,4-triazol-3-yl]methyl]isoindole-1,3-dione Chemical class C=1C=CC=C(N2C(=NN=C2)CN2C(C3=CC=CC=C3C2=O)=O)C=1C(=O)C1=CC=CC=C1 KXXARNCTHSKODN-UHFFFAOYSA-N 0.000 description 2
- JWBVUHHLOMZGOY-UHFFFAOYSA-N 2-[[4-[2-(2-chlorobenzoyl)-4-fluorophenyl]-5-[(dimethylamino)methyl]-1,2,4-triazol-3-yl]methyl]isoindole-1,3-dione Chemical compound CN(C)CC1=NN=C(CN2C(C3=CC=CC=C3C2=O)=O)N1C1=CC=C(F)C=C1C(=O)C1=CC=CC=C1Cl JWBVUHHLOMZGOY-UHFFFAOYSA-N 0.000 description 2
- VOSWLRFZRNIKEJ-UHFFFAOYSA-N 2-[[4-[2-(2-chlorobenzoyl)-4-nitrophenyl]-5-[(dimethylamino)methyl]-1,2,4-triazol-3-yl]methyl]isoindole-1,3-dione Chemical compound CN(C)CC1=NN=C(CN2C(C3=CC=CC=C3C2=O)=O)N1C1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1Cl VOSWLRFZRNIKEJ-UHFFFAOYSA-N 0.000 description 2
- JNAKGWMCGUIQCA-UHFFFAOYSA-N 2-[[4-[4-chloro-2-(2-chlorobenzoyl)phenyl]-5-[[di(propan-2-yl)amino]methyl]-1,2,4-triazol-3-yl]methyl]isoindole-1,3-dione Chemical compound CC(C)N(C(C)C)CC1=NN=C(CN2C(C3=CC=CC=C3C2=O)=O)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl JNAKGWMCGUIQCA-UHFFFAOYSA-N 0.000 description 2
- LXKHUPSNFJCLOL-UHFFFAOYSA-N 2-[[4-[4-chloro-2-(2-chlorobenzoyl)phenyl]-5-[[ethyl(methyl)amino]methyl]-1,2,4-triazol-3-yl]methyl]isoindole-1,3-dione Chemical compound CCN(C)CC1=NN=C(CN2C(C3=CC=CC=C3C2=O)=O)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl LXKHUPSNFJCLOL-UHFFFAOYSA-N 0.000 description 2
- BXBSDHSVTCGOFC-UHFFFAOYSA-N 3-amino-4-phenylquinazolin-4-ol Chemical compound NN1C=NC2=CC=CC=C2C1(O)C1=CC=CC=C1 BXBSDHSVTCGOFC-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000538 analytical sample Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- QHYNXXQYSDCYJU-UHFFFAOYSA-N (6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)methanamine Chemical class C12=CC=CC=C2N2C(CN)=NN=C2CN=C1C1=CC=CC=C1 QHYNXXQYSDCYJU-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 1
- KZFYOVBBOIVHNC-UHFFFAOYSA-N 1-(8-bromo-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)-n,n-dimethylmethanamine Chemical compound C12=CC(Br)=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1 KZFYOVBBOIVHNC-UHFFFAOYSA-N 0.000 description 1
- WHKXZGLZSWIZSS-UHFFFAOYSA-N 1-(8-fluoro-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)-n,n-dimethylmethanamine Chemical compound C12=CC(F)=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1 WHKXZGLZSWIZSS-UHFFFAOYSA-N 0.000 description 1
- LRKYLKBLUJXTFL-UHFFFAOYSA-N 1-(piperidin-1-ylmethyl)piperidine Chemical compound C1CCCCN1CN1CCCCC1 LRKYLKBLUJXTFL-UHFFFAOYSA-N 0.000 description 1
- OUIPTZRCCVRRNA-UHFFFAOYSA-N 1-[10-chloro-6-(2-chlorophenyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]-n,n-dimethylmethanamine Chemical compound C12=CC=CC(Cl)=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1Cl OUIPTZRCCVRRNA-UHFFFAOYSA-N 0.000 description 1
- DMYPPBJCBRLQEE-UHFFFAOYSA-N 1-[6-(2-bromophenyl)-9-nitro-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]-n,n-dimethylmethanamine Chemical compound C12=CC=C([N+]([O-])=O)C=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1Br DMYPPBJCBRLQEE-UHFFFAOYSA-N 0.000 description 1
- RXCBJYLIJODACT-UHFFFAOYSA-N 1-[6-(2-chlorophenyl)-8-(trifluoromethyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]-n,n-dimethylmethanamine Chemical compound C12=CC(C(F)(F)F)=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1Cl RXCBJYLIJODACT-UHFFFAOYSA-N 0.000 description 1
- NFKBEJFYDAYBSB-UHFFFAOYSA-N 1-[6-(2-chlorophenyl)-8-fluoro-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]-n,n-dimethylmethanamine Chemical compound C12=CC(F)=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1Cl NFKBEJFYDAYBSB-UHFFFAOYSA-N 0.000 description 1
- DIPFASDTUQPOIP-UHFFFAOYSA-N 1-[6-(2-chlorophenyl)-8-nitro-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]-n,n-dimethylmethanamine Chemical compound C12=CC([N+]([O-])=O)=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1Cl DIPFASDTUQPOIP-UHFFFAOYSA-N 0.000 description 1
- UCASETBNKRDYRL-UHFFFAOYSA-N 1-[6-(2-chlorophenyl)-9-(trifluoromethyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]-n,n-dimethylmethanamine Chemical compound C12=CC=C(C(F)(F)F)C=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1Cl UCASETBNKRDYRL-UHFFFAOYSA-N 0.000 description 1
- YQYKFUGDIWZIRL-UHFFFAOYSA-N 1-[6-(4-bromophenyl)-10-fluoro-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]-n,n-dimethylmethanamine Chemical compound C12=CC=CC(F)=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=C(Br)C=C1 YQYKFUGDIWZIRL-UHFFFAOYSA-N 0.000 description 1
- LDEVTRGHPZJFDV-UHFFFAOYSA-N 1-[7-fluoro-6-(3-fluorophenyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]-n,n-dimethylmethanamine Chemical compound C12=C(F)C=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC(F)=C1 LDEVTRGHPZJFDV-UHFFFAOYSA-N 0.000 description 1
- RTRYDCCPKISLAY-UHFFFAOYSA-N 1-[9-bromo-6-(2,6-difluorophenyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]-n,n-dimethylmethanamine Chemical compound C12=CC=C(Br)C=C2N2C(CN(C)C)=NN=C2CN=C1C1=C(F)C=CC=C1F RTRYDCCPKISLAY-UHFFFAOYSA-N 0.000 description 1
- ZMBGDHSFLFMTPQ-UHFFFAOYSA-N 1-methyl-4-[(4-methylpiperazin-1-yl)methyl]piperazine Chemical compound C1CN(C)CCN1CN1CCN(C)CC1 ZMBGDHSFLFMTPQ-UHFFFAOYSA-N 0.000 description 1
- UKTYEBXAHDYZSU-UHFFFAOYSA-M 1-methyl-4-methylidenepiperazin-4-ium;chloride Chemical compound [Cl-].CN1CC[N+](=C)CC1 UKTYEBXAHDYZSU-UHFFFAOYSA-M 0.000 description 1
- SVUMJBMMPVDJQA-UHFFFAOYSA-M 1-methylidenepiperidin-1-ium;chloride Chemical compound [Cl-].C=[N+]1CCCCC1 SVUMJBMMPVDJQA-UHFFFAOYSA-M 0.000 description 1
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- 239000002178 crystalline material Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- KSWZQIKAXKUXJM-UHFFFAOYSA-M di(propylidene)azanium;chloride Chemical compound [Cl-].CCC=[N+]=CCC KSWZQIKAXKUXJM-UHFFFAOYSA-M 0.000 description 1
- 229960005215 dichloroacetic acid Drugs 0.000 description 1
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LDRXRPMOZCMADG-UHFFFAOYSA-N ethyl(methylidene)azanium chloride Chemical compound [Cl-].C(C)[NH+]=C LDRXRPMOZCMADG-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- UNEXJVCWJSHFNN-UHFFFAOYSA-N n,n,n',n'-tetraethylmethanediamine Chemical compound CCN(CC)CN(CC)CC UNEXJVCWJSHFNN-UHFFFAOYSA-N 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- OUGDNLWJKYDPDQ-UHFFFAOYSA-N n,n-dimethyl-1-(6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)methanamine Chemical compound C12=CC=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1 OUGDNLWJKYDPDQ-UHFFFAOYSA-N 0.000 description 1
- OOWSGSAZXWEDCA-UHFFFAOYSA-N n,n-dimethyl-1-(7-nitro-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)methanamine Chemical compound C1=CC=C([N+]([O-])=O)C2=C1N1C(CN(C)C)=NN=C1CN=C2C1=CC=CC=C1 OOWSGSAZXWEDCA-UHFFFAOYSA-N 0.000 description 1
- LQXZYQVIANZLKS-UHFFFAOYSA-N n,n-dimethyl-1-(8-nitro-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)methanamine Chemical compound C12=CC([N+]([O-])=O)=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1 LQXZYQVIANZLKS-UHFFFAOYSA-N 0.000 description 1
- RQHUKNYXQSLRQB-UHFFFAOYSA-N n,n-dimethyl-1-[6-phenyl-8-(trifluoromethyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]methanamine Chemical compound C12=CC(C(F)(F)F)=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1 RQHUKNYXQSLRQB-UHFFFAOYSA-N 0.000 description 1
- NUSHELRLSJLWBO-UHFFFAOYSA-N n-[(8-chloro-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)methyl]-n-ethylethanamine Chemical compound C12=CC(Cl)=CC=C2N2C(CN(CC)CC)=NN=C2CN=C1C1=CC=CC=C1 NUSHELRLSJLWBO-UHFFFAOYSA-N 0.000 description 1
- JNBYRVLXSKRMQG-UHFFFAOYSA-N n-[(9-nitro-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)methyl]-n-propan-2-ylpropan-2-amine Chemical compound C12=CC=C([N+]([O-])=O)C=C2N2C(CN(C(C)C)C(C)C)=NN=C2CN=C1C1=CC=CC=C1 JNBYRVLXSKRMQG-UHFFFAOYSA-N 0.000 description 1
- HPVUTFZVVTXQGB-UHFFFAOYSA-N n-[[6-(2-chlorophenyl)-8-nitro-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]methyl]-n-methylethanamine Chemical compound C12=CC([N+]([O-])=O)=CC=C2N2C(CN(C)CC)=NN=C2CN=C1C1=CC=CC=C1Cl HPVUTFZVVTXQGB-UHFFFAOYSA-N 0.000 description 1
- LBIJNKHDFNJCBY-UHFFFAOYSA-N n-[[7-chloro-6-(2-fluorophenyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]methyl]-n-ethylethanamine Chemical compound C12=C(Cl)C=CC=C2N2C(CN(CC)CC)=NN=C2CN=C1C1=CC=CC=C1F LBIJNKHDFNJCBY-UHFFFAOYSA-N 0.000 description 1
- NKVHZWNOAKPLMJ-UHFFFAOYSA-N n-[[8-chloro-6-(2-chlorophenyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]methyl]-n-methylethanamine Chemical compound C12=CC(Cl)=CC=C2N2C(CN(C)CC)=NN=C2CN=C1C1=CC=CC=C1Cl NKVHZWNOAKPLMJ-UHFFFAOYSA-N 0.000 description 1
- QJJXKGKSFWBILZ-UHFFFAOYSA-N n-[[8-chloro-6-(2-chlorophenyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]methyl]-n-propan-2-ylpropan-2-amine Chemical compound C12=CC(Cl)=CC=C2N2C(CN(C(C)C)C(C)C)=NN=C2CN=C1C1=CC=CC=C1Cl QJJXKGKSFWBILZ-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/480,979 US3957761A (en) | 1973-02-14 | 1974-06-19 | Process for the production of 1-aminomethyl-6-phenyl-4h-s-triazolo-[4,3-a][1]benzodiazepines and intermediates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5116695A JPS5116695A (ja) | 1976-02-10 |
| JPS6242910B2 true JPS6242910B2 (enrdf_load_stackoverflow) | 1987-09-10 |
Family
ID=23910093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6769775A Granted JPS5116695A (ja) | 1974-06-19 | 1975-06-06 | Jukikagobutsutoseiho |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5116695A (enrdf_load_stackoverflow) |
| BE (1) | BE830430A (enrdf_load_stackoverflow) |
| CA (1) | CA1055490A (enrdf_load_stackoverflow) |
| CH (1) | CH613206A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2526380A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2275467A1 (enrdf_load_stackoverflow) |
| GB (2) | GB1475459A (enrdf_load_stackoverflow) |
| NL (1) | NL7507295A (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4194049A (en) * | 1979-03-29 | 1980-03-18 | Hoffmann-La Roche Inc. | 2-[[2-Methyl-1-[2-benzoyl(or benzyl)phenyl]-1H-imidazol-5-yl]methyl]-1H-isoindole-1,3(2H)-diones |
| US4474699A (en) * | 1983-05-25 | 1984-10-02 | The Upjohn Company | Preparing 1-aminomethyl-6-substituted-4H-s-triazolo[4,3-a][1,4]benzodiazepines in improved procedures |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT283368B (de) * | 1966-09-12 | 1970-08-10 | Dresden Arzneimittel | Verfahren zur herstellung von 1,4-benzodiazepinen |
| JPS4932874B1 (enrdf_load_stackoverflow) * | 1970-12-11 | 1974-09-03 |
-
1975
- 1975-05-22 CA CA227,597A patent/CA1055490A/en not_active Expired
- 1975-06-06 JP JP6769775A patent/JPS5116695A/ja active Granted
- 1975-06-09 CH CH743375A patent/CH613206A5/xx not_active IP Right Cessation
- 1975-06-10 GB GB2474075A patent/GB1475459A/en not_active Expired
- 1975-06-10 GB GB4891776A patent/GB1475460A/en not_active Expired
- 1975-06-13 DE DE19752526380 patent/DE2526380A1/de active Granted
- 1975-06-18 FR FR7519139A patent/FR2275467A1/fr active Granted
- 1975-06-19 BE BE157498A patent/BE830430A/xx not_active IP Right Cessation
- 1975-06-19 NL NL7507295A patent/NL7507295A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AU8156575A (en) | 1976-12-02 |
| DE2526380A1 (de) | 1976-01-08 |
| CH613206A5 (en) | 1979-09-14 |
| BE830430A (fr) | 1975-12-19 |
| FR2275467B1 (enrdf_load_stackoverflow) | 1978-09-22 |
| CA1055490A (en) | 1979-05-29 |
| JPS5116695A (ja) | 1976-02-10 |
| GB1475459A (en) | 1977-06-01 |
| GB1475460A (en) | 1977-06-01 |
| FR2275467A1 (fr) | 1976-01-16 |
| NL7507295A (nl) | 1975-12-23 |
| DE2526380C2 (enrdf_load_stackoverflow) | 1987-12-17 |
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