CH570403A5 - 4-H s-Triazolo (4,3-a) (1,4) benzodiazepins - CNS inhibitors psychosed-atives, and anticonvulsants - Google Patents
4-H s-Triazolo (4,3-a) (1,4) benzodiazepins - CNS inhibitors psychosed-atives, and anticonvulsantsInfo
- Publication number
- CH570403A5 CH570403A5 CH1170272A CH1170272A CH570403A5 CH 570403 A5 CH570403 A5 CH 570403A5 CH 1170272 A CH1170272 A CH 1170272A CH 1170272 A CH1170272 A CH 1170272A CH 570403 A5 CH570403 A5 CH 570403A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- substituted
- chlorine
- general formula
- ring
- Prior art date
Links
- 239000001961 anticonvulsive agent Substances 0.000 title description 2
- 229940125681 anticonvulsant agent Drugs 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 33
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 20
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 239000004312 hexamethylene tetramine Substances 0.000 claims abstract description 7
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- -1 polymethyleneimino Polymers 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 44
- 239000000460 chlorine Substances 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 20
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 19
- 239000011737 fluorine Substances 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 8
- 150000007522 mineralic acids Chemical class 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 229910052740 iodine Chemical group 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 235000005985 organic acids Nutrition 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000002576 diazepinyl group Chemical class N1N=C(C=CC=C1)* 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- HCEREIMHQSSOEB-UHFFFAOYSA-N 8-chloro-6-(2-fluorophenyl)-1-[(4-methoxyphenyl)methoxymethyl]-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C1=CC(OC)=CC=C1COCC1=NN=C2N1C1=CC=C(Cl)C=C1C(C=1C(=CC=CC=1)F)=NC2 HCEREIMHQSSOEB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 7
- 150000002431 hydrogen Chemical group 0.000 claims 7
- 239000011630 iodine Chemical group 0.000 claims 5
- 229940049706 benzodiazepine Drugs 0.000 claims 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims 1
- AMYOWKQRDBWPTM-UHFFFAOYSA-N 8-chloro-1-(ethoxymethyl)-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C12=CC(Cl)=CC=C2N2C(COCC)=NN=C2CN=C1C1=CC=CC=C1 AMYOWKQRDBWPTM-UHFFFAOYSA-N 0.000 claims 1
- ICBHFKOKXBUCCA-UHFFFAOYSA-N 8-chloro-1-(methoxymethyl)-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C12=CC(Cl)=CC=C2N2C(COC)=NN=C2CN=C1C1=CC=CC=C1 ICBHFKOKXBUCCA-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003513 alkali Substances 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 235000011114 ammonium hydroxide Nutrition 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 150000003949 imides Chemical class 0.000 abstract 1
- 229960004011 methenamine Drugs 0.000 abstract 1
- 238000006476 reductive cyclization reaction Methods 0.000 abstract 1
- 238000003797 solvolysis reaction Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WXILCXHXMMBIHC-UHFFFAOYSA-N 1,4-benzodiazepin-1-ylmethanol Chemical compound OCN1C=CN=CC2=CC=CC=C12 WXILCXHXMMBIHC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 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
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000002539 anti-aggressive effect Effects 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000002920 convulsive effect Effects 0.000 description 2
- 229930003836 cresol Natural products 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QWCFYWXKNDIGLW-UHFFFAOYSA-N 8-chloro-1-(2-ethoxyethyl)-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C12=CC(Cl)=CC=C2N2C(CCOCC)=NN=C2CN=C1C1=CC=CC=C1 QWCFYWXKNDIGLW-UHFFFAOYSA-N 0.000 description 1
- CDWFTGWLVQVFCH-UHFFFAOYSA-N 8-chloro-1-[(4-methoxyphenyl)methoxymethyl]-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C1=CC(OC)=CC=C1COCC1=NN=C2N1C1=CC=C(Cl)C=C1C(C=1C=CC=CC=1)=NC2 CDWFTGWLVQVFCH-UHFFFAOYSA-N 0.000 description 1
- CINUDEPRPAIRHL-UHFFFAOYSA-N 8-chloro-6-phenyl-1-(2-phenylmethoxyethyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C=1C(Cl)=CC=C(N23)C=1C(C=1C=CC=CC=1)=NCC3=NN=C2CCOCC1=CC=CC=C1 CINUDEPRPAIRHL-UHFFFAOYSA-N 0.000 description 1
- CNXMBTJLZMMNHE-UHFFFAOYSA-N 8-chloro-6-phenyl-1-(phenylmethoxymethyl)-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C=1C(Cl)=CC=C(N23)C=1C(C=1C=CC=CC=1)=NCC3=NN=C2COCC1=CC=CC=C1 CNXMBTJLZMMNHE-UHFFFAOYSA-N 0.000 description 1
- MXWGZZHBHTXJHO-UHFFFAOYSA-N C(C)OCCC1=NN=C(N1C1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)Cl)CCl Chemical compound C(C)OCCC1=NN=C(N1C1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)Cl)CCl MXWGZZHBHTXJHO-UHFFFAOYSA-N 0.000 description 1
- IJLVJNJDKBYHOD-UHFFFAOYSA-N COC1=CC=C(COCC2=NN=C(CCl)N2C2=C(C=C(Cl)C=C2)C(=O)C2=CC=CC=C2)C=C1 Chemical compound COC1=CC=C(COCC2=NN=C(CCl)N2C2=C(C=C(Cl)C=C2)C(=O)C2=CC=CC=C2)C=C1 IJLVJNJDKBYHOD-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 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 1
- 241001465754 Metazoa Species 0.000 description 1
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 241001279009 Strychnos toxifera Species 0.000 description 1
- 208000010513 Stupor Diseases 0.000 description 1
- WFAWYCLDZAVUFW-UHFFFAOYSA-N [5-chloro-2-[3-(chloromethyl)-5-(ethoxymethyl)-1,2,4-triazol-4-yl]phenyl]-phenylmethanone Chemical compound C(C)OCC1=NN=C(N1C1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)Cl)CCl WFAWYCLDZAVUFW-UHFFFAOYSA-N 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 125000001691 aryl alkyl amino group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1170272A CH570403A5 (en) | 1972-08-08 | 1972-08-08 | 4-H s-Triazolo (4,3-a) (1,4) benzodiazepins - CNS inhibitors psychosed-atives, and anticonvulsants |
| SE7309472A SE408059B (sv) | 1972-08-08 | 1973-07-05 | Forfarande for framstellning av s-triazolo(4,3-a)(1,4)besodiazepinderivat |
| CA177,764A CA992078A (en) | 1972-08-08 | 1973-07-31 | Process for the production of new triazolo-benzodiazepines |
| DD17272373A DD106385A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-08-08 | 1973-08-06 | |
| NL7310900A NL7310900A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-08-08 | 1973-08-07 | |
| AR24950373A AR201009A1 (es) | 1972-08-08 | 1973-08-08 | Procedimiento para la obtencion de derivados de diazepina |
| JP8995973A JPS4945097A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-08-08 | 1973-08-08 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1170272A CH570403A5 (en) | 1972-08-08 | 1972-08-08 | 4-H s-Triazolo (4,3-a) (1,4) benzodiazepins - CNS inhibitors psychosed-atives, and anticonvulsants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH570403A5 true CH570403A5 (en) | 1975-12-15 |
Family
ID=4376045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1170272A CH570403A5 (en) | 1972-08-08 | 1972-08-08 | 4-H s-Triazolo (4,3-a) (1,4) benzodiazepins - CNS inhibitors psychosed-atives, and anticonvulsants |
Country Status (7)
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU251571A (en) * | 1970-10-07 | 1979-12-31 | Takeda Chemical Industries Ltd | Process for preparing trazolobenzodiazepine derivatives |
-
1972
- 1972-08-08 CH CH1170272A patent/CH570403A5/de not_active IP Right Cessation
-
1973
- 1973-07-05 SE SE7309472A patent/SE408059B/xx unknown
- 1973-07-31 CA CA177,764A patent/CA992078A/en not_active Expired
- 1973-08-06 DD DD17272373A patent/DD106385A5/xx unknown
- 1973-08-07 NL NL7310900A patent/NL7310900A/xx not_active Application Discontinuation
- 1973-08-08 JP JP8995973A patent/JPS4945097A/ja active Pending
- 1973-08-08 AR AR24950373A patent/AR201009A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| DD106385A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-06-12 |
| CA992078A (en) | 1976-06-29 |
| JPS4945097A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-04-27 |
| SE408059B (sv) | 1979-05-14 |
| AR201009A1 (es) | 1975-02-06 |
| NL7310900A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-02-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2609486C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| CH619953A5 (en) | Process for the preparation of diazepine derivatives | |
| EP0059390A1 (de) | Imidazodiazepine, Zwischenprodukte und Verfahren für ihre Herstellung, sowie diese enthaltende Arzneimittel | |
| EP0075855B1 (de) | 7-Brom-5-(2-halogenphenyl)-1H-2,3-dihydro-1,4-benzodiazepin-Verbindungen sowie Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2156472A1 (de) | Verfahren zur Herstellung von neuen Diazepinderivaten | |
| EP0387618A1 (de) | 1,7-anellierte 1H-Indol-2-carbonsäure-N-(1,4-benzodiazepin-3-yl)amide | |
| US4342755A (en) | Tranquillo-sedative benzodiazepine derivatives | |
| US4587245A (en) | Method of treating neuropsychic disturbances by benzodiazepine derivatives and composition therefor | |
| DE2712309A1 (de) | As-triazinobenzodiazepin-1-one, benzodiazepine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel | |
| DE2215943A1 (de) | Neue 6-Phenyl-4H-s-triazolo eckige Klammer auf 1,5-a eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu benzodiazepin-2-carbonsäuren und ihre Ester, sowie Verfahren zu deren Herstellung | |
| DE2201210A1 (de) | Neue Diazepinderivate und Verfahren zu ihrer Herstellung | |
| DE2308280A1 (de) | Verfahren zur herstellung von neuen diazepinderivaten | |
| CH570403A5 (en) | 4-H s-Triazolo (4,3-a) (1,4) benzodiazepins - CNS inhibitors psychosed-atives, and anticonvulsants | |
| EP0054839B1 (de) | 2-Acylaminomethyl-1,4-benzodiazepine und deren Salze sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| AT330786B (de) | Verfahren zur herstellung von neuen diazepinderivaten | |
| DE2251291A1 (de) | Benzodiazepinderivate und verfahren zu ihrer herstellung | |
| AT330787B (de) | Verfahren zur herstellung von neuen diazepinderivaten und deren salzen | |
| DE69612413T2 (de) | 1-(Hetero)Arylvinyl-5H-2,3-benzodiazepinderivative verwendbar zur Behandlung von Erkrankungen des Zentralnervensystems, sowie Benzopyrylium Intermediate zu ihrer Herstellung | |
| CH567024A5 (en) | 1-Aminoalkyl-triazolo(4,3-a) (1,4) benzodiazepines - CNS depressants prepd. from corresp 1-phthalimidoalkyl cpds by treatment with hydrazine or acid | |
| CH561722A5 (en) | 1-(Substd. methyl)triazolo(4,3-a)(1,4)benzodiazepines - CNS depressants prepd. by reacting a hydrazide with 2-aminobenzodiazepines | |
| CH513190A (de) | Verfahren zur Herstellung von neuen Imidazolidinonderivaten | |
| CH574961A5 (en) | 4,5-dihydro-4h-s-triazolo (4,3-a) (1,4) benzodiazepine - cns depressants, anti-convulsants, anti-aggressives and somatic reflex in | |
| CH568319A5 (en) | 1-Dialkylaminoalkyl-4H-s-triazolo/4,3-A//1.4/benzodiazepines prepn - by reductive alkylation of 1-monoalkylamino or 1-primary amino cpds | |
| CH567023A5 (en) | 1-Aminoalkyl-triazolo(4,3-a) (1,4) benzodiazepines - CNS depressants prepd. by reducing corresp 1-azidoalkyl cpds | |
| AT317231B (de) | Verfahren zur Herstellung von neuen Diazepinderivaten sowie deren 5-Oxyden und deren Säureadditionssalzen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |