CA1055023A - Process for the production of 1-((dmethylamino) methyl)-6-phenyl-4h-triazolo (4,3-a) (1,4)-benzodiazepine - Google Patents
Process for the production of 1-((dmethylamino) methyl)-6-phenyl-4h-triazolo (4,3-a) (1,4)-benzodiazepineInfo
- Publication number
- CA1055023A CA1055023A CA261,702A CA261702A CA1055023A CA 1055023 A CA1055023 A CA 1055023A CA 261702 A CA261702 A CA 261702A CA 1055023 A CA1055023 A CA 1055023A
- Authority
- CA
- Canada
- Prior art keywords
- triazolo
- benzodiazepine
- methyl
- dimethylamino
- chloro
- 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
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 title abstract description 22
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims abstract description 30
- 150000001450 anions Chemical class 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 19
- 229940049706 benzodiazepine Drugs 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- GJSLOMWRLALDCT-UHFFFAOYSA-N adinazolam Chemical compound C12=CC(Cl)=CC=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=C1 GJSLOMWRLALDCT-UHFFFAOYSA-N 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- GTXINZZVQCXXQH-UHFFFAOYSA-N 8-bromo-6-pyridin-2-yl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C=1C(Br)=CC=C(N2C=NN=C2CN=2)C=1C=2C1=CC=CC=N1 GTXINZZVQCXXQH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- BDQFWTZESHZRGW-UHFFFAOYSA-N 8-chloro-6-(2-chlorophenyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C=1C(Cl)=CC=C(N2C=NN=C2CN=2)C=1C=2C1=CC=CC=C1Cl BDQFWTZESHZRGW-UHFFFAOYSA-N 0.000 claims 1
- 150000001557 benzodiazepines Chemical class 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 9
- 239000002253 acid Substances 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- 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 abstract 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 12
- FEQAUBVIUZJXKN-UHFFFAOYSA-N propan-2-imine;hydrochloride Chemical compound [Cl-].CC(C)=[NH2+] FEQAUBVIUZJXKN-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- -1 hydrochloric Chemical class 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- HOLLFLKWFBXREI-UHFFFAOYSA-N propan-2-ylideneazanium;iodide Chemical compound [I-].CC(C)=[NH2+] HOLLFLKWFBXREI-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- AZMZAJKQVSINMH-UHFFFAOYSA-N 8-chloro-6-pyridin-2-yl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C=1C(Cl)=CC=C(N2C=NN=C2CN=2)C=1C=2C1=CC=CC=N1 AZMZAJKQVSINMH-UHFFFAOYSA-N 0.000 description 2
- 238000006683 Mannich reaction Methods 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 150000002431 hydrogen Chemical group 0.000 description 2
- VGIVLIHKENZQHQ-UHFFFAOYSA-N n,n,n',n'-tetramethylmethanediamine Chemical compound CN(C)CN(C)C VGIVLIHKENZQHQ-UHFFFAOYSA-N 0.000 description 2
- LZTIRMBLYYPMNW-UHFFFAOYSA-N propan-2-ylideneazanium;bromide Chemical compound [Br-].CC(C)=[NH2+] LZTIRMBLYYPMNW-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JGOAAVOJJHOUPB-UHFFFAOYSA-N 1-(10-bromo-6-pyridin-2-yl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)-n,n-dimethylmethanamine Chemical compound C12=CC=CC(Br)=C2N2C(CN(C)C)=NN=C2CN=C1C1=CC=CC=N1 JGOAAVOJJHOUPB-UHFFFAOYSA-N 0.000 description 1
- NEKJHAZVABZDGB-UHFFFAOYSA-N 1-(7-bromo-3-methyl-6-pyridin-2-yl-3a,4-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)-n,n-dimethylmethanamine Chemical compound C12=C(Br)C=CC=C2N2C(CN(C)C)=NN(C)C2CN=C1C1=CC=CC=N1 NEKJHAZVABZDGB-UHFFFAOYSA-N 0.000 description 1
- RSQCZLCOJDBWFZ-UHFFFAOYSA-N 1-(7-bromo-4-methyl-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)-n,n-dimethylmethanamine Chemical compound C12=C(Br)C=CC=C2N2C(CN(C)C)=NN=C2C(C)N=C1C1=CC=CC=C1 RSQCZLCOJDBWFZ-UHFFFAOYSA-N 0.000 description 1
- HPMRAOUUNSIMDM-UHFFFAOYSA-N 1-(8-bromo-6-pyridin-2-yl-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=N1 HPMRAOUUNSIMDM-UHFFFAOYSA-N 0.000 description 1
- GXFGZTGUOACUBW-UHFFFAOYSA-N 1-(9-bromo-4-methyl-6-phenyl-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=C2C(C)N=C1C1=CC=CC=C1 GXFGZTGUOACUBW-UHFFFAOYSA-N 0.000 description 1
- DPMUBRJZLAYKMC-UHFFFAOYSA-N 1-[6-(2-chlorophenyl)-2,4-dimethyl-9-nitro-1,4-dihydro-[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)N(C)N=C2C(C)N=C1C1=CC=CC=C1Cl DPMUBRJZLAYKMC-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
- BZCVDSXWPIWIOS-UHFFFAOYSA-N 1-[8-bromo-6-(2-chlorophenyl)-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=C1Cl BZCVDSXWPIWIOS-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
- COMSVUTXEQMBSD-UHFFFAOYSA-N 4-[5-(4-bromophenyl)-1,7-dihydrotetrazolo[1,5-a]pyrimidin-7-yl]-n,n-dimethylaniline Chemical compound C1=CC(N(C)C)=CC=C1C1N2NN=NC2=NC(C=2C=CC(Br)=CC=2)=C1 COMSVUTXEQMBSD-UHFFFAOYSA-N 0.000 description 1
- BZIOPPKOOJWWFK-UHFFFAOYSA-N 6-(2-chlorophenyl)-8-(trifluoromethyl)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound FC(C=1C=CC2=C(C(=NCC=3N2C=NN3)C3=C(C=CC=C3)Cl)C1)(F)F BZIOPPKOOJWWFK-UHFFFAOYSA-N 0.000 description 1
- XRBLBGJPAHGGOZ-UHFFFAOYSA-N 6-(2-chlorophenyl)-8-fluoro-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C=1C(F)=CC=C(N2C=NN=C2CN=2)C=1C=2C1=CC=CC=C1Cl XRBLBGJPAHGGOZ-UHFFFAOYSA-N 0.000 description 1
- NOFZIRANIQMLHX-UHFFFAOYSA-N 6-(2-chlorophenyl)-8-nitro-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C=1C([N+](=O)[O-])=CC=C(N2C=NN=C2CN=2)C=1C=2C1=CC=CC=C1Cl NOFZIRANIQMLHX-UHFFFAOYSA-N 0.000 description 1
- GSIGZZKHXAAYOA-UHFFFAOYSA-N 6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C12=CC=CC=C2N2C=NN=C2CN=C1C1=CC=CC=C1 GSIGZZKHXAAYOA-UHFFFAOYSA-N 0.000 description 1
- NLIOYGQRRCHAGC-UHFFFAOYSA-N 6-pyridin-2-yl-8-(trifluoromethyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C=1C(C(F)(F)F)=CC=C(N2C=NN=C2CN=2)C=1C=2C1=CC=CC=N1 NLIOYGQRRCHAGC-UHFFFAOYSA-N 0.000 description 1
- BFNNDAQKGDMARG-UHFFFAOYSA-N 7-bromo-3-methyl-6-pyridin-2-yl-3a,4-dihydro-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound CN1N=CN(C2=CC=CC(Br)=C22)C1CN=C2C1=CC=CC=N1 BFNNDAQKGDMARG-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000004908 diazepines Chemical class 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- 230000000694 effects Effects 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
- DOSCWKGAAHEHBV-UHFFFAOYSA-N n,n-dimethyl-1-(6-pyridin-2-yl-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=N1 DOSCWKGAAHEHBV-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000063 preceeding effect Effects 0.000 description 1
- XDAGXZXKTKRFMT-UHFFFAOYSA-N propan-2-imine Chemical compound CC(C)=N XDAGXZXKTKRFMT-UHFFFAOYSA-N 0.000 description 1
- FDEFAULBNJJAKK-UHFFFAOYSA-N propan-2-ylideneazanium;2,2,2-trifluoroacetate Chemical compound CC(C)=[NH2+].[O-]C(=O)C(F)(F)F FDEFAULBNJJAKK-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
Classifications
-
- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/623,972 US4001262A (en) | 1975-10-20 | 1975-10-20 | Process for the production of 1-[(dimethylamino)methyl]-6-phenyl-4H-triazolo[4,3-a][1,4]-benzodiazepine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1055023A true CA1055023A (en) | 1979-05-22 |
Family
ID=24500089
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA261,702A Expired CA1055023A (en) | 1975-10-20 | 1976-09-21 | Process for the production of 1-((dmethylamino) methyl)-6-phenyl-4h-triazolo (4,3-a) (1,4)-benzodiazepine |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4001262A (en, 2012) |
| JP (1) | JPS6019311B2 (en, 2012) |
| BE (1) | BE847466A (en, 2012) |
| CA (1) | CA1055023A (en, 2012) |
| CH (1) | CH623314A5 (en, 2012) |
| DE (1) | DE2647177A1 (en, 2012) |
| FR (1) | FR2328708A1 (en, 2012) |
| GB (1) | GB1491667A (en, 2012) |
| MX (1) | MX3719E (en, 2012) |
| NL (1) | NL7610072A (en, 2012) |
| PL (1) | PL105275B1 (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4075221A (en) * | 1977-01-24 | 1978-02-21 | The Upjohn Company | Process for preparing triazolobenzodiazepines |
| US4472397A (en) * | 1983-02-18 | 1984-09-18 | The Upjohn Company | Use of certain 1-substituted-triazolo-benzodiazepines to treat psychoses |
| US4501698A (en) * | 1983-03-31 | 1985-02-26 | The Upjohn Company | Preparing 1-(hydroxymethyl)-triazolobenzodiazepines and 1-(aminomethyl)-triazolobenzodiazepines |
| 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 |
| JPH0631404U (ja) * | 1992-09-28 | 1994-04-26 | ヤンマー農機株式会社 | 農用トラクタの作業機横移動装置 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3842090A (en) | 1973-02-14 | 1974-10-15 | Upjohn Co | Certain 1-aminomethyl-6-phenyl 4h-s-triazolo(4,3-a)(1,4)benzodiazepines |
-
1975
- 1975-10-20 US US05/623,972 patent/US4001262A/en not_active Expired - Lifetime
-
1976
- 1976-09-02 MX MX764878U patent/MX3719E/es unknown
- 1976-09-10 NL NL7610072A patent/NL7610072A/xx not_active Application Discontinuation
- 1976-09-21 CA CA261,702A patent/CA1055023A/en not_active Expired
- 1976-09-29 GB GB40338/76A patent/GB1491667A/en not_active Expired
- 1976-10-18 CH CH1318676A patent/CH623314A5/de not_active IP Right Cessation
- 1976-10-19 PL PL1976193128A patent/PL105275B1/pl unknown
- 1976-10-19 FR FR7631427A patent/FR2328708A1/fr active Granted
- 1976-10-19 DE DE19762647177 patent/DE2647177A1/de not_active Withdrawn
- 1976-10-20 BE BE171657A patent/BE847466A/xx not_active IP Right Cessation
- 1976-10-20 JP JP51126018A patent/JPS6019311B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH623314A5 (en, 2012) | 1981-05-29 |
| US4001262A (en) | 1977-01-04 |
| FR2328708B3 (en, 2012) | 1980-11-07 |
| DE2647177A1 (de) | 1977-04-28 |
| BE847466A (fr) | 1977-04-20 |
| PL105275B1 (pl) | 1979-10-31 |
| FR2328708A1 (fr) | 1977-05-20 |
| JPS5251398A (en) | 1977-04-25 |
| NL7610072A (nl) | 1977-04-22 |
| MX3719E (es) | 1981-05-21 |
| JPS6019311B2 (ja) | 1985-05-15 |
| GB1491667A (en) | 1977-11-09 |
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