PL80171B1 - - Google Patents
Download PDFInfo
- Publication number
- PL80171B1 PL80171B1 PL13474369A PL13474369A PL80171B1 PL 80171 B1 PL80171 B1 PL 80171B1 PL 13474369 A PL13474369 A PL 13474369A PL 13474369 A PL13474369 A PL 13474369A PL 80171 B1 PL80171 B1 PL 80171B1
- Authority
- PL
- Poland
- Prior art keywords
- pattern
- methyl
- formula
- dione
- benzodiazepine
- Prior art date
Links
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 48
- -1 alkyl radical Chemical class 0.000 claims description 38
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000003254 radicals Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000002367 halogens Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000001879 copper Chemical class 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 150000002825 nitriles Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229910001868 water Inorganic materials 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 101100231508 Caenorhabditis elegans ceh-5 gene Proteins 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001502 aryl halides Chemical class 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- UNFHOAZOCIELCW-UHFFFAOYSA-N 1,5-dihydro-1,5-benzodiazepine-2,4-dione Chemical class N1C(=O)CC(=O)NC2=CC=CC=C21 UNFHOAZOCIELCW-UHFFFAOYSA-N 0.000 description 1
- NZZYMDHMGHIKLN-UHFFFAOYSA-N 1-methyl-5-phenyl-1,5-benzodiazepine-2,4-dione Chemical compound O=C1CC(=O)N(C)C2=CC=CC=C2N1C1=CC=CC=C1 NZZYMDHMGHIKLN-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- NBKNFNAHFNVUOW-UHFFFAOYSA-N 3-ethoxy-3-oxopropanoic acid;hydrochloride Chemical compound Cl.CCOC(=O)CC(O)=O NBKNFNAHFNVUOW-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- LUTBHMSHJATKIS-UHFFFAOYSA-N 4-chloro-n-methyl-2-nitroaniline Chemical compound CNC1=CC=C(Cl)C=C1[N+]([O-])=O LUTBHMSHJATKIS-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- SWNNXMVVKBMLIN-UHFFFAOYSA-N 7-bromo-1-methyl-5-phenyl-1,5-benzodiazepine-2,4-dione Chemical compound O=C1CC(=O)N(C)C2=CC=C(Br)C=C2N1C1=CC=CC=C1 SWNNXMVVKBMLIN-UHFFFAOYSA-N 0.000 description 1
- BHUVEGOQFYWSKR-UHFFFAOYSA-N C1CCC([Rh])CC1 Chemical compound C1CCC([Rh])CC1 BHUVEGOQFYWSKR-UHFFFAOYSA-N 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- 101100275770 Caenorhabditis elegans cri-3 gene Proteins 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 108010093488 His-His-His-His-His-His Proteins 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 description 1
- 101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
- CXOXHMZGEKVPMT-UHFFFAOYSA-N clobazam Chemical compound O=C1CC(=O)N(C)C2=CC=C(Cl)C=C2N1C1=CC=CC=C1 CXOXHMZGEKVPMT-UHFFFAOYSA-N 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-AHCXROLUSA-N copper-60 Chemical compound [60Cu] RYGMFSIKBFXOCR-AHCXROLUSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT677768A AT286302B (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer 5-Aryl-1H-1,5-benzodiazepin-2,4-3H,5H-dione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL80171B1 true PL80171B1 (enrdf_load_stackoverflow) | 1975-08-30 |
Family
ID=3589652
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL13474369A PL80171B1 (enrdf_load_stackoverflow) | 1968-07-12 | 1969-07-11 |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT286302B (enrdf_load_stackoverflow) |
| BG (1) | BG15690A3 (enrdf_load_stackoverflow) |
| BR (1) | BR6910669D0 (enrdf_load_stackoverflow) |
| DK (1) | DK126942B (enrdf_load_stackoverflow) |
| ES (1) | ES369347A1 (enrdf_load_stackoverflow) |
| FI (1) | FI49410C (enrdf_load_stackoverflow) |
| PL (1) | PL80171B1 (enrdf_load_stackoverflow) |
| SU (1) | SU374825A3 (enrdf_load_stackoverflow) |
-
1968
- 1968-07-12 AT AT677768A patent/AT286302B/de not_active IP Right Cessation
-
1969
- 1969-07-07 SU SU1345273A patent/SU374825A3/ru active
- 1969-07-10 BG BG012625A patent/BG15690A3/bg unknown
- 1969-07-10 ES ES369347A patent/ES369347A1/es not_active Expired
- 1969-07-10 FI FI204969A patent/FI49410C/fi active
- 1969-07-11 PL PL13474369A patent/PL80171B1/pl unknown
- 1969-07-11 DK DK377669A patent/DK126942B/da unknown
- 1969-07-13 BR BR21066969A patent/BR6910669D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK126942B (da) | 1973-09-03 |
| BR6910669D0 (pt) | 1973-02-15 |
| BG15690A3 (bg) | 1976-06-21 |
| AT286302B (de) | 1970-12-10 |
| SU374825A3 (enrdf_load_stackoverflow) | 1973-03-20 |
| FI49410C (fi) | 1975-06-10 |
| FI49410B (enrdf_load_stackoverflow) | 1975-02-28 |
| ES369347A1 (es) | 1971-06-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3100770A (en) | 5-pyridyl-1,4-benzodiazepine compounds | |
| CA1134362A (en) | Benzimidazoles, their preparation and their use as pharmaceutical compositions | |
| PL124063B1 (en) | Process for preparing novel derivatives of 5h-2,3-benzodiazepine | |
| FI63234B (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara 6-enyl-4h-imidazo(1,5-a)(1,4)diazepinfoereningar | |
| SK279902B6 (sk) | Triazolpyrimidínové deriváty, farmaceutický prostr | |
| FI59099C (fi) | Foerfarande foer framstaellning av terapeutiskt vaerdefulla substituerade 6-fenyl-4h-s-triazolo-/3,4c/-tieno-/2,3e/-1,4-diazepiner | |
| US4118386A (en) | Synthesis of imidazo[1,5-a]diazepine-3-carboxylates | |
| EP0126970A2 (en) | Anxiolytic and anti-depressant thienopyridine derivatives | |
| PL97040B1 (pl) | Sposob wytwarzania 3-fluorobenzodwuazepin-2-onow | |
| PL93127B1 (enrdf_load_stackoverflow) | ||
| US4183932A (en) | Fused quinazolinones and preparation thereof | |
| PL80171B1 (enrdf_load_stackoverflow) | ||
| US3485841A (en) | Azirino(1,2-a) quinazoline 2-oxide and preparation thereof | |
| PL88788B1 (en) | Triazolo-isoindole and triazolo-isoquinoline derivatives and their manufacture and uses[gb1477302a] | |
| US3849405A (en) | Thieno-(2,3-e)(1,4)diazepin-2-ones | |
| NO126799B (enrdf_load_stackoverflow) | ||
| US3398139A (en) | Process for preparing 2-amino-benzodiazepines | |
| PL78769B1 (enrdf_load_stackoverflow) | ||
| US3819627A (en) | 1-substituted-3,4-dihydro-2(1h)-quinazolinones | |
| PL174330B1 (pl) | Nowe pochodne 3-oksadiazolilo-5,6,7,8-tetrahydro-1,6-naftyrydyny, nowe pochodne 5,6,7,8-tetrahydro-1,6-naftyrydyny oraz sposób otrzymywania pochodnych 1,6-naftyrydyny | |
| US4333944A (en) | 8-Halo-6-phenyl-4H-s-triazolo (3,4-c) thieno 1,4-diazepin-1-ones | |
| US3625959A (en) | Preparation of 2,3,4,5-tetrahydro-5-phenyl-1h-1, 4-benzodiazepin-4-ols | |
| Sasaki et al. | The synthesis of novel polycyclic heterocyclic ring systems via photocyclization. 8.[1] Benzothieno [2, 3‐c] naphtho [1, 2‐h] quinoline and [1] benzothieno [2, 3‐c] naphtho [1, 2‐h][1, 2, 4] triazolo [4, 3‐a] quinoline | |
| PL106837B1 (pl) | Sposob wytwarzania imidazo 1,5-a1,4 diazepin | |
| DE1934607A1 (de) | Verfahren zur Herstellung neuer 5-Aryl-1H-1,5-benzodiazepin-2,4-dione |