PL92135B1 - - Google Patents
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- Publication number
- PL92135B1 PL92135B1 PL1973178210A PL17821073A PL92135B1 PL 92135 B1 PL92135 B1 PL 92135B1 PL 1973178210 A PL1973178210 A PL 1973178210A PL 17821073 A PL17821073 A PL 17821073A PL 92135 B1 PL92135 B1 PL 92135B1
- Authority
- PL
- Poland
- Prior art keywords
- group
- methylene
- general formula
- benzodiazepin
- chlorophenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- -1 morpholino, thiomorpholino Chemical group 0.000 claims description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Chemical group 0.000 claims description 7
- 239000000460 chlorine Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 239000011630 iodine Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 4
- 229910052731 fluorine Inorganic materials 0.000 claims 4
- 239000011737 fluorine Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 239000004202 carbamide Substances 0.000 claims 2
- 235000013877 carbamide Nutrition 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 24
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 16
- 229910021529 ammonia Inorganic materials 0.000 description 12
- 239000006260 foam Substances 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 9
- 238000002329 infrared spectrum Methods 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
- 238000002211 ultraviolet spectrum Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 5
- TVCAWAUYNBFJEE-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-3-(dimethylaminomethylidene)-1H-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(=CN(C)C)N=C1C1=CC=CC=C1Cl TVCAWAUYNBFJEE-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- AAAYQZTZQYGHQF-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-3-(dimethylaminomethylidene)-1-methyl-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2N(C)C(=O)C(=CN(C)C)N=C1C1=CC=CC=C1Cl AAAYQZTZQYGHQF-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000001961 anticonvulsive agent Substances 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical compound O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 description 3
- IPTIQGWZJIRGAX-UHFFFAOYSA-N 7-bromo-5-(2-chlorophenyl)-3-(dimethylaminomethylidene)-1H-1,4-benzodiazepin-2-one Chemical compound C12=CC(Br)=CC=C2NC(=O)C(=CN(C)C)N=C1C1=CC=CC=C1Cl IPTIQGWZJIRGAX-UHFFFAOYSA-N 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 210000003205 muscle Anatomy 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000002040 relaxant effect Effects 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RIUPGPYCWKJQKQ-UHFFFAOYSA-N 3-(aminomethylidene)-7-bromo-5-(2-chlorophenyl)-1-methyl-1,4-benzodiazepin-2-one Chemical group N=1C(=CN)C(=O)N(C)C2=CC=C(Br)C=C2C=1C1=CC=CC=C1Cl RIUPGPYCWKJQKQ-UHFFFAOYSA-N 0.000 description 2
- DJRJECOUTOWTPU-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-fluoro-1-methyl-3-(morpholin-4-ylmethylidene)-1,4-benzodiazepin-2-one Chemical compound O=C1N(C)C2=CC=C(F)C=C2C(C=2C(=CC=CC=2)Cl)=NC1=CN1CCOCC1 DJRJECOUTOWTPU-UHFFFAOYSA-N 0.000 description 2
- XPLMCWVQQNNCKP-UHFFFAOYSA-N 7-bromo-5-(2-chlorophenyl)-3-(dimethylaminomethylidene)-1-methyl-1,4-benzodiazepin-2-one Chemical compound C12=CC(Br)=CC=C2N(C)C(=O)C(=CN(C)C)N=C1C1=CC=CC=C1Cl XPLMCWVQQNNCKP-UHFFFAOYSA-N 0.000 description 2
- DOIVOPCCTULFST-UHFFFAOYSA-N 7-chloro-3-(dimethylaminomethylidene)-1-methyl-5-phenyl-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2N(C)C(=O)C(=CN(C)C)N=C1C1=CC=CC=C1 DOIVOPCCTULFST-UHFFFAOYSA-N 0.000 description 2
- UYSURIQHGFXCMU-UHFFFAOYSA-N 7-chloro-3-(dimethylaminomethylidene)-5-phenyl-1H-1,4-benzodiazepin-2-one Chemical compound ClC=1C=CC2=C(C(=NC(C(N2)=O)=CN(C)C)C2=CC=CC=C2)C1 UYSURIQHGFXCMU-UHFFFAOYSA-N 0.000 description 2
- PMQCEFKZYNHZRW-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-3-[[cyclohexyl(methyl)amino]methylidene]-1H-1,4-benzodiazepin-2-one Chemical compound C1CCCCC1N(C)C=C(C(NC1=CC=C(Cl)C=C11)=O)N=C1C1=CC=CC=C1Cl PMQCEFKZYNHZRW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 229940125681 anticonvulsant agent Drugs 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 150000002169 ethanolamines Chemical class 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000003956 methylamines Chemical class 0.000 description 2
- 230000004899 motility Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 description 1
- YLRSPHVBGSAJJA-UHFFFAOYSA-N 1-methyl-3h-1,4-benzodiazepin-2-one Chemical compound C1=NCC(=O)N(C)C2=CC=CC=C21 YLRSPHVBGSAJJA-UHFFFAOYSA-N 0.000 description 1
- BHUKCEYZKFAGEY-UHFFFAOYSA-N 2-(methylamino)-1-morpholin-4-ylethanone Chemical compound CNCC(=O)N1CCOCC1 BHUKCEYZKFAGEY-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- YKAQLXPNVBRPFZ-UHFFFAOYSA-N 3-(aminomethylidene)-5-(2-chlorophenyl)-1-methyl-7-nitro-1,4-benzodiazepin-2-one Chemical compound N=1C(=CN)C(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1Cl YKAQLXPNVBRPFZ-UHFFFAOYSA-N 0.000 description 1
- ATMUGBIRXFNYLG-UHFFFAOYSA-N 3-(aminomethylidene)-5-(2-chlorophenyl)-7-fluoro-1-methyl-1,4-benzodiazepin-2-one Chemical compound N=1C(=CN)C(=O)N(C)C2=CC=C(F)C=C2C=1C1=CC=CC=C1Cl ATMUGBIRXFNYLG-UHFFFAOYSA-N 0.000 description 1
- ORBLZLQSJNMUFE-UHFFFAOYSA-N 3-(aminomethylidene)-5-(2-chlorophenyl)-7-fluoro-1H-1,4-benzodiazepin-2-one Chemical compound C12=CC(F)=CC=C2NC(=O)C(=CN)N=C1C1=CC=CC=C1Cl ORBLZLQSJNMUFE-UHFFFAOYSA-N 0.000 description 1
- UDCGANSTKILWIB-UHFFFAOYSA-N 3-(aminomethylidene)-7-bromo-5-(2-chlorophenyl)-1H-1,4-benzodiazepin-2-one Chemical compound NC=C1C(NC2=C(C(=N1)C1=C(C=CC=C1)Cl)C=C(C=C2)Br)=O UDCGANSTKILWIB-UHFFFAOYSA-N 0.000 description 1
- HWURBLVQTJHQJF-UHFFFAOYSA-N 3-(aminomethylidene)-7-chloro-1-methyl-5-phenyl-1,4-benzodiazepin-2-one Chemical compound NC=C1C(N(C2=C(C(=N1)C1=CC=CC=C1)C=C(C=C2)Cl)C)=O HWURBLVQTJHQJF-UHFFFAOYSA-N 0.000 description 1
- QQRHECNQDPTIIE-UHFFFAOYSA-N 3-(aminomethylidene)-7-chloro-5-(2-chlorophenyl)-1-methyl-1,4-benzodiazepin-2-one Chemical compound N=1C(=CN)C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl QQRHECNQDPTIIE-UHFFFAOYSA-N 0.000 description 1
- LHTXBAFRWUJAQV-UHFFFAOYSA-N 3-(aminomethylidene)-7-chloro-5-phenyl-1H-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(=CN)N=C1C1=CC=CC=C1 LHTXBAFRWUJAQV-UHFFFAOYSA-N 0.000 description 1
- VMOWOPLHSHGXRH-UHFFFAOYSA-N 3-(butylaminomethylidene)-5-(2-chlorophenyl)-1-methyl-7-nitro-1,4-benzodiazepin-2-one Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(C)C(=O)C(=CNCCCC)N=C1C1=CC=CC=C1Cl VMOWOPLHSHGXRH-UHFFFAOYSA-N 0.000 description 1
- XZTLRPIGSGBZSI-UHFFFAOYSA-N 3-(butylaminomethylidene)-5-(2-chlorophenyl)-7-nitro-1H-1,4-benzodiazepin-2-one Chemical compound C12=CC([N+]([O-])=O)=CC=C2NC(=O)C(=CNCCCC)N=C1C1=CC=CC=C1Cl XZTLRPIGSGBZSI-UHFFFAOYSA-N 0.000 description 1
- JGCXJFMPLBYJLB-UHFFFAOYSA-N 3-(butylaminomethylidene)-7-chloro-5-(2-chlorophenyl)-1-methyl-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2N(C)C(=O)C(=CNCCCC)N=C1C1=CC=CC=C1Cl JGCXJFMPLBYJLB-UHFFFAOYSA-N 0.000 description 1
- YHXYJVYUOVMQGC-UHFFFAOYSA-N 3-(butylaminomethylidene)-7-chloro-5-(2-chlorophenyl)-1H-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(=CNCCCC)N=C1C1=CC=CC=C1Cl YHXYJVYUOVMQGC-UHFFFAOYSA-N 0.000 description 1
- TUPARKCVWDQMDS-UHFFFAOYSA-N 3-(dimethylaminomethylidene)-5-(2-fluorophenyl)-1-methyl-7-nitro-1,4-benzodiazepin-2-one Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(C)C(=O)C(=CN(C)C)N=C1C1=CC=CC=C1F TUPARKCVWDQMDS-UHFFFAOYSA-N 0.000 description 1
- JCXCANVELQLSSL-UHFFFAOYSA-N 3-(dimethylaminomethylidene)-5-(2-fluorophenyl)-7-nitro-1H-1,4-benzodiazepin-2-one Chemical compound C12=CC([N+]([O-])=O)=CC=C2NC(=O)C(=CN(C)C)N=C1C1=CC=CC=C1F JCXCANVELQLSSL-UHFFFAOYSA-N 0.000 description 1
- AKTFOTBENHWMKZ-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(diethylaminomethylidene)-1-[2-(dimethylamino)ethyl]-7-nitro-1,4-benzodiazepin-2-one Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(CCN(C)C)C(=O)C(=CN(CC)CC)N=C1C1=CC=CC=C1Cl AKTFOTBENHWMKZ-UHFFFAOYSA-N 0.000 description 1
- KYYGSUQOHQJSCG-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(diethylaminomethylidene)-7-nitro-1H-1,4-benzodiazepin-2-one Chemical compound C12=CC([N+]([O-])=O)=CC=C2NC(=O)C(=CN(CC)CC)N=C1C1=CC=CC=C1Cl KYYGSUQOHQJSCG-UHFFFAOYSA-N 0.000 description 1
- OSEJOGGAQPGDDQ-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(dimethylaminomethylidene)-7-fluoro-1-methyl-1,4-benzodiazepin-2-one Chemical compound C12=CC(F)=CC=C2N(C)C(=O)C(=CN(C)C)N=C1C1=CC=CC=C1Cl OSEJOGGAQPGDDQ-UHFFFAOYSA-N 0.000 description 1
- OCUNQXJGXNHXIV-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(dimethylaminomethylidene)-7-fluoro-1H-1,4-benzodiazepin-2-one Chemical compound C12=CC(F)=CC=C2NC(=O)C(=CN(C)C)N=C1C1=CC=CC=C1Cl OCUNQXJGXNHXIV-UHFFFAOYSA-N 0.000 description 1
- YMVUBLFBIUCJES-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(ethylaminomethylidene)-7-iodo-1-methyl-1,4-benzodiazepin-2-one Chemical compound C12=CC(I)=CC=C2N(C)C(=O)C(=CNCC)N=C1C1=CC=CC=C1Cl YMVUBLFBIUCJES-UHFFFAOYSA-N 0.000 description 1
- SRRBNFWOYDYPKJ-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-(ethylaminomethylidene)-7-nitro-1H-1,4-benzodiazepin-2-one Chemical compound C(C)NC=C1C(NC2=C(C(=N1)C1=C(C=CC=C1)Cl)C=C(C=C2)[N+](=O)[O-])=O SRRBNFWOYDYPKJ-UHFFFAOYSA-N 0.000 description 1
- CBCIKUIHFSKQDH-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-fluoro-3-(morpholin-4-ylmethylidene)-1H-1,4-benzodiazepin-2-one Chemical compound N1=C(C=2C(=CC=CC=2)Cl)C2=CC(F)=CC=C2NC(=O)C1=CN1CCOCC1 CBCIKUIHFSKQDH-UHFFFAOYSA-N 0.000 description 1
- JPPGPYKLSRQYMM-UHFFFAOYSA-N 7-bromo-5-(2-chlorophenyl)-1-methyl-3-(methylaminomethylidene)-1,4-benzodiazepin-2-one Chemical compound C12=CC(Br)=CC=C2N(C)C(=O)C(=CNC)N=C1C1=CC=CC=C1Cl JPPGPYKLSRQYMM-UHFFFAOYSA-N 0.000 description 1
- YRHGJNLBSNSMHU-UHFFFAOYSA-N 7-bromo-5-(2-chlorophenyl)-3-(ethylaminomethylidene)-1-methyl-1,4-benzodiazepin-2-one Chemical compound C12=CC(Br)=CC=C2N(C)C(=O)C(=CNCC)N=C1C1=CC=CC=C1Cl YRHGJNLBSNSMHU-UHFFFAOYSA-N 0.000 description 1
- QVGYOOYIBMPZCA-UHFFFAOYSA-N 7-bromo-5-(2-chlorophenyl)-3-(ethylaminomethylidene)-1H-1,4-benzodiazepin-2-one Chemical compound C12=CC(Br)=CC=C2NC(=O)C(=CNCC)N=C1C1=CC=CC=C1Cl QVGYOOYIBMPZCA-UHFFFAOYSA-N 0.000 description 1
- MLZNSHHDYKUZRD-UHFFFAOYSA-N 7-chloro-3-(ethylaminomethylidene)-5-(2-fluorophenyl)-1-methyl-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2N(C)C(=O)C(=CNCC)N=C1C1=CC=CC=C1F MLZNSHHDYKUZRD-UHFFFAOYSA-N 0.000 description 1
- RCKYPJDRHVWZOK-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-1-(cyclopropylmethyl)-3-(dimethylaminomethylidene)-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2N(CC2CC2)C(=O)C(=CN(C)C)N=C1C1=CC=CC=C1Cl RCKYPJDRHVWZOK-UHFFFAOYSA-N 0.000 description 1
- BTGITORGBVFIHX-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-1-methyl-3-(morpholin-4-ylmethylidene)-1,4-benzodiazepin-2-one Chemical compound O=C1N(C)C2=CC=C(Cl)C=C2C(C=2C(=CC=CC=2)Cl)=NC1=CN1CCOCC1 BTGITORGBVFIHX-UHFFFAOYSA-N 0.000 description 1
- ORXONJDJQGCVLG-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-1-methyl-3-(propylaminomethylidene)-1,4-benzodiazepin-2-one Chemical compound ClC=1C=CC2=C(C(=NC(C(N2C)=O)=CNCCC)C2=C(C=CC=C2)Cl)C1 ORXONJDJQGCVLG-UHFFFAOYSA-N 0.000 description 1
- CBZIWDHPQJQHFI-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-3-(diethylaminomethylidene)-1H-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(=CN(CC)CC)N=C1C1=CC=CC=C1Cl CBZIWDHPQJQHFI-UHFFFAOYSA-N 0.000 description 1
- IKPVGRQCXGVQDM-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-3-(ethylaminomethylidene)-1-methyl-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2N(C)C(=O)C(=CNCC)N=C1C1=CC=CC=C1Cl IKPVGRQCXGVQDM-UHFFFAOYSA-N 0.000 description 1
- JTUAOBZTPSRBCS-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-3-(methylaminomethylidene)-1H-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(=CNC)N=C1C1=CC=CC=C1Cl JTUAOBZTPSRBCS-UHFFFAOYSA-N 0.000 description 1
- ZONXHQPSZQBVRT-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-3-(morpholin-4-ylmethylidene)-1H-1,4-benzodiazepin-2-one Chemical compound N1=C(C=2C(=CC=CC=2)Cl)C2=CC(Cl)=CC=C2NC(=O)C1=CN1CCOCC1 ZONXHQPSZQBVRT-UHFFFAOYSA-N 0.000 description 1
- VZFMGUYWFBXIJN-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-3-[(dibutylamino)methylidene]-1H-1,4-benzodiazepin-2-one Chemical compound C(CCC)N(CCCC)C=C1C(NC2=C(C(=N1)C1=C(C=CC=C1)Cl)C=C(C=C2)Cl)=O VZFMGUYWFBXIJN-UHFFFAOYSA-N 0.000 description 1
- ZTZFZHSIDDPPLU-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-3-[(dipropylamino)methylidene]-1H-1,4-benzodiazepin-2-one Chemical compound C(CC)N(CCC)C=C1C(NC2=C(C(=N1)C1=C(C=CC=C1)Cl)C=C(C=C2)Cl)=O ZTZFZHSIDDPPLU-UHFFFAOYSA-N 0.000 description 1
- XLTJDEOEVWDSMD-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-3-[[2-(diethylamino)ethylamino]methylidene]-1H-1,4-benzodiazepin-2-one Chemical compound ClC=1C=CC2=C(C(=NC(C(N2)=O)=CNCCN(CC)CC)C2=C(C=CC=C2)Cl)C1 XLTJDEOEVWDSMD-UHFFFAOYSA-N 0.000 description 1
- YPCORXAEDQEIQC-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-3-[[di(propan-2-yl)amino]methylidene]-1-methyl-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2N(C)C(=O)C(=CN(C(C)C)C(C)C)N=C1C1=CC=CC=C1Cl YPCORXAEDQEIQC-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical group C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- BEIUBAKCCUVQNA-UHFFFAOYSA-N CC(C)(C)NC=C1N=C(C(C=CC=C2)=C2Cl)C(C=C(C=C2)Cl)=C2NC1=O Chemical compound CC(C)(C)NC=C1N=C(C(C=CC=C2)=C2Cl)C(C=C(C=C2)Cl)=C2NC1=O BEIUBAKCCUVQNA-UHFFFAOYSA-N 0.000 description 1
- HXBYFEKRDIACCT-UHFFFAOYSA-N CCNC=C1C(=O)NC2=C(C=C(C=C2)I)C(=N1)C3=CC=CC=C3Cl Chemical compound CCNC=C1C(=O)NC2=C(C=C(C=C2)I)C(=N1)C3=CC=CC=C3Cl HXBYFEKRDIACCT-UHFFFAOYSA-N 0.000 description 1
- OJDWXULVQVIJHK-UHFFFAOYSA-N CN1C2=C(C=C(C=C2)Br)C(=NC(=CNC3CC3)C1=O)C4=CC=CC=C4Cl Chemical compound CN1C2=C(C=C(C=C2)Br)C(=NC(=CNC3CC3)C1=O)C4=CC=CC=C4Cl OJDWXULVQVIJHK-UHFFFAOYSA-N 0.000 description 1
- IWOBHYHFMCRLOJ-UHFFFAOYSA-N CNC=C1C(=O)NC2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3 Chemical compound CNC=C1C(=O)NC2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3 IWOBHYHFMCRLOJ-UHFFFAOYSA-N 0.000 description 1
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 238000011785 NMRI mouse Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- ZVTQWXCKQTUVPY-UHFFFAOYSA-N chloromethylcyclopropane Chemical compound ClCC1CC1 ZVTQWXCKQTUVPY-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000003941 n-butylamines Chemical class 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 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
- 230000001681 protective effect Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722234150 DE2234150A1 (de) | 1972-07-12 | 1972-07-12 | Neue 1,4-benzodiazepine |
| DE2324962A DE2324962A1 (de) | 1973-05-15 | 1973-05-15 | Neue 1,4-benzodiazepine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL92135B1 true PL92135B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-03-31 |
Family
ID=25763551
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1973178210A PL92135B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-07-12 | 1973-07-11 |
Country Status (9)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2502621B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1981-03-27 | 1983-10-28 | Roussel Uclaf |
-
1973
- 1973-07-05 US US376378A patent/US3872090A/en not_active Expired - Lifetime
- 1973-07-06 PH PH14798A patent/PH10572A/en unknown
- 1973-07-09 CH CH1370876A patent/CH590854A5/xx not_active IP Right Cessation
- 1973-07-10 BG BG26529A patent/BG20599A3/xx unknown
- 1973-07-11 PL PL1973178210A patent/PL92135B1/pl unknown
- 1973-07-11 NL NL7309651A patent/NL7309651A/xx unknown
- 1973-07-12 FR FR7325606A patent/FR2191906B1/fr not_active Expired
-
1974
- 1974-01-16 ES ES422319A patent/ES422319A1/es not_active Expired
- 1974-10-09 SU SU2065465A patent/SU559650A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| SU559650A3 (ru) | 1977-05-25 |
| US3872090A (en) | 1975-03-18 |
| ES422319A1 (es) | 1976-04-16 |
| FR2191906A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-02-08 |
| PH10572A (en) | 1977-06-30 |
| BG20599A3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-12-05 |
| FR2191906B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-08-13 |
| CH590854A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-08-31 |
| NL7309651A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-01-15 |
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