CA1055490A - Process for preparing triazolobenzodiazepines - Google Patents
Process for preparing triazolobenzodiazepinesInfo
- Publication number
- CA1055490A CA1055490A CA227,597A CA227597A CA1055490A CA 1055490 A CA1055490 A CA 1055490A CA 227597 A CA227597 A CA 227597A CA 1055490 A CA1055490 A CA 1055490A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- methyl
- chloro
- triazol
- benzophenone
- 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
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 238000000034 method Methods 0.000 claims abstract description 25
- -1 pyrrolidino, piperidino Chemical group 0.000 claims abstract description 21
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- FEQAUBVIUZJXKN-UHFFFAOYSA-N propan-2-imine;hydrochloride Chemical group [Cl-].CC(C)=[NH2+] FEQAUBVIUZJXKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 229910052736 halogen Chemical group 0.000 claims 4
- 150000002367 halogens Chemical group 0.000 claims 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 229940125904 compound 1 Drugs 0.000 claims 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims 1
- 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 claims 1
- ZAXFFQSOWYVGER-UHFFFAOYSA-N 3-amino-6-chloro-4-phenylquinazolin-4-ol Chemical compound NN1C=NC2=CC=C(Cl)C=C2C1(O)C1=CC=CC=C1 ZAXFFQSOWYVGER-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 239000012965 benzophenone Substances 0.000 abstract description 86
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract description 79
- 239000002253 acid Substances 0.000 abstract description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract description 11
- 125000001309 chloro group Chemical group Cl* 0.000 abstract description 6
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 6
- 239000000543 intermediate Substances 0.000 abstract description 6
- 125000001246 bromo group Chemical group Br* 0.000 abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract description 2
- GVNKOMOSYDQGIC-UHFFFAOYSA-N 2h-triazolo[4,5-i][1,2]benzodiazepin-1-ylmethanamine Chemical class C1=CN=NC2=C3N(CN)NN=C3C=CC2=C1 GVNKOMOSYDQGIC-UHFFFAOYSA-N 0.000 abstract 1
- 208000019901 Anxiety disease Diseases 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- 230000036506 anxiety Effects 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229940024874 benzophenone Drugs 0.000 description 83
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 description 26
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 25
- 239000000725 suspension Substances 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 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 12
- 229940049706 benzodiazepine Drugs 0.000 description 12
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 12
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 11
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 11
- 239000012346 acetyl chloride Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 125000001401 1,2,4-triazol-4-yl group Chemical group N=1N=C([H])N([*])C=1[H] 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 4
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- LKRNZLYYWVHIFZ-UHFFFAOYSA-N 4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C1N=CC2=CC=CC=C2N2C=NN=C12 LKRNZLYYWVHIFZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 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 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
- 239000000538 analytical sample Substances 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 2
- 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
- WQINSVOOIJDOLJ-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)acetic acid Chemical compound C1=CC=C2C(=O)N(CC(=O)O)C(=O)C2=C1 WQINSVOOIJDOLJ-UHFFFAOYSA-N 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 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
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- WVRIJHGUJNXDRZ-UHFFFAOYSA-N ethane-1,1-diamine Chemical compound CC(N)N WVRIJHGUJNXDRZ-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- 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
- 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
- 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 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
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- ZYKYVZPUUGVMFE-UHFFFAOYSA-N 2-(2,3-dihydroindol-1-yl)acetic acid Chemical compound C1=CC=C2N(CC(=O)O)CCC2=C1 ZYKYVZPUUGVMFE-UHFFFAOYSA-N 0.000 description 1
- LPZOCVVDSHQFST-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-ethylpyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CC LPZOCVVDSHQFST-UHFFFAOYSA-N 0.000 description 1
- NMLSQGQMTQVIDO-UHFFFAOYSA-N 2-[[4-(2-benzoyl-4-bromophenyl)-1,2,4-triazol-3-yl]methyl]isoindole-1,3-dione Chemical compound C=1C(Br)=CC=C(N2C(=NN=C2)CN2C(C3=CC=CC=C3C2=O)=O)C=1C(=O)C1=CC=CC=C1 NMLSQGQMTQVIDO-UHFFFAOYSA-N 0.000 description 1
- ZXWVENBEIRWQLQ-UHFFFAOYSA-N 2-[[4-(2-benzoyl-4-chlorophenyl)-5-[(dipropylamino)methyl]-1,2,4-triazol-3-yl]methyl]isoindole-1,3-dione Chemical compound CCCN(CCC)CC1=NN=C(CN2C(C3=CC=CC=C3C2=O)=O)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZXWVENBEIRWQLQ-UHFFFAOYSA-N 0.000 description 1
- PUUTXNWTPZOHLO-UHFFFAOYSA-N 2-[[4-[2-(2-chlorobenzoyl)-4-nitrophenyl]-1,2,4-triazol-3-yl]methyl]isoindole-1,3-dione Chemical compound C=1C([N+](=O)[O-])=CC=C(N2C(=NN=C2)CN2C(C3=CC=CC=C3C2=O)=O)C=1C(=O)C1=CC=CC=C1Cl PUUTXNWTPZOHLO-UHFFFAOYSA-N 0.000 description 1
- BJDXONGYRRYVSV-UHFFFAOYSA-N 2-[[4-[2-(4-bromobenzoyl)-6-fluorophenyl]-1,2,4-triazol-3-yl]methyl]isoindole-1,3-dione Chemical compound C1=NN=C(CN2C(C3=CC=CC=C3C2=O)=O)N1C=1C(F)=CC=CC=1C(=O)C1=CC=C(Br)C=C1 BJDXONGYRRYVSV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- KYTDHERQCOHXDQ-UHFFFAOYSA-N 2-[[5-(aminomethyl)-4-(2-benzoylphenyl)-1,2,4-triazol-3-yl]methyl]isoindole-1,3-dione Chemical class NCC1=NN=C(CN2C(C3=CC=CC=C3C2=O)=O)N1C1=CC=CC=C1C(=O)C1=CC=CC=C1 KYTDHERQCOHXDQ-UHFFFAOYSA-N 0.000 description 1
- MMYJPMPKQAAMFR-UHFFFAOYSA-N 4-[[8-chloro-6-(2-chlorophenyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl]methyl]morpholine Chemical compound C=1C(Cl)=CC=C(N23)C=1C(C=1C(=CC=CC=1)Cl)=NCC3=NN=C2CN1CCOCC1 MMYJPMPKQAAMFR-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- XYEGHAIFYJPHBQ-UHFFFAOYSA-M 4-methylidenemorpholin-4-ium;chloride Chemical compound [Cl-].C=[N+]1CCOCC1 XYEGHAIFYJPHBQ-UHFFFAOYSA-M 0.000 description 1
- WTHWPBIXDSCTPM-UHFFFAOYSA-N 6-(2-chlorophenyl)-8-fluoro-1-(pyrrolidin-1-ylmethyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C=1C(F)=CC=C(N23)C=1C(C=1C(=CC=CC=1)Cl)=NCC3=NN=C2CN1CCCC1 WTHWPBIXDSCTPM-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000861718 Chloris <Aves> Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- UQONAEXHTGDOIH-AWEZNQCLSA-N O=C(N1CC[C@@H](C1)N1CCCC1=O)C1=CC2=C(NC3(CC3)CCO2)N=C1 Chemical compound O=C(N1CC[C@@H](C1)N1CCCC1=O)C1=CC2=C(NC3(CC3)CCO2)N=C1 UQONAEXHTGDOIH-AWEZNQCLSA-N 0.000 description 1
- 241000199911 Peridinium Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- XBIPSSUMUYALFF-UHFFFAOYSA-M [Cl-].C(CC)C=[N+]=CCCC Chemical compound [Cl-].C(CC)C=[N+]=CCCC XBIPSSUMUYALFF-UHFFFAOYSA-M 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical compound COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- KSWZQIKAXKUXJM-UHFFFAOYSA-M di(propylidene)azanium;chloride Chemical compound [Cl-].CCC=[N+]=CCC KSWZQIKAXKUXJM-UHFFFAOYSA-M 0.000 description 1
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- YVXVCPIGIIATBS-UHFFFAOYSA-N ethyl-methyl-methylideneazanium Chemical compound CC[N+](C)=C YVXVCPIGIIATBS-UHFFFAOYSA-N 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)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
- 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
- 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
- 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
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- XDAGXZXKTKRFMT-UHFFFAOYSA-N propan-2-imine Chemical compound CC(C)=N XDAGXZXKTKRFMT-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA310,228A CA1051905A (en) | 1974-06-19 | 1978-08-29 | 1,3-dioxo-2-isoindolineacetic acid, [[n-(2-benzoyl-phenyl)-1, 3-dioxo-2-isoindolineacetamido] methylene] hydrazides |
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 (1)
| Publication Number | Publication Date |
|---|---|
| CA1055490A true CA1055490A (en) | 1979-05-29 |
Family
ID=23910093
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA227,597A Expired CA1055490A (en) | 1974-06-19 | 1975-05-22 | Process for preparing triazolobenzodiazepines |
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 NL NL7507295A patent/NL7507295A/xx not_active Application Discontinuation
- 1975-06-19 BE BE157498A patent/BE830430A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH613206A5 (en) | 1979-09-14 |
| DE2526380C2 (enrdf_load_stackoverflow) | 1987-12-17 |
| NL7507295A (nl) | 1975-12-23 |
| FR2275467B1 (enrdf_load_stackoverflow) | 1978-09-22 |
| BE830430A (fr) | 1975-12-19 |
| JPS6242910B2 (enrdf_load_stackoverflow) | 1987-09-10 |
| AU8156575A (en) | 1976-12-02 |
| GB1475460A (en) | 1977-06-01 |
| DE2526380A1 (de) | 1976-01-08 |
| GB1475459A (en) | 1977-06-01 |
| JPS5116695A (ja) | 1976-02-10 |
| FR2275467A1 (fr) | 1976-01-16 |
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