DE1445412B - - Google Patents
Info
- Publication number
- DE1445412B DE1445412B DE1445412B DE 1445412 B DE1445412 B DE 1445412B DE 1445412 B DE1445412 B DE 1445412B
- Authority
- DE
- Germany
- Prior art keywords
- radical
- benzodiazepin
- dihydro
- general formula
- phenyl
- 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.)
- Pending
Links
- 239000000460 chlorine Substances 0.000 claims description 15
- -1 methoxy, methyl Chemical group 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004946 alkenylalkyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000004458 analytical method Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 4
- 239000007787 solid Substances 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
- MDPJHNGFYGSHME-UHFFFAOYSA-N 5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine Chemical compound C12=CC=CC=C2NCCN=C1C1=CC=CC=C1 MDPJHNGFYGSHME-UHFFFAOYSA-N 0.000 description 2
- GGRWZBVSUZZMKS-UHFFFAOYSA-N Demoxepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C[N+]([O-])=C1C1=CC=CC=C1 GGRWZBVSUZZMKS-UHFFFAOYSA-N 0.000 description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000001145 hydrido group Chemical group *[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-N (2E)-3-phenylprop-2-enoic acid Chemical group OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- QQUIWIVTEWQHKA-UHFFFAOYSA-N 3H-1,4-benzodiazepine Chemical compound C1=NCC=NC2=CC=CC=C21 QQUIWIVTEWQHKA-UHFFFAOYSA-N 0.000 description 1
- IVUAAOBNUNMJQC-UHFFFAOYSA-N 5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC=CC=C2NC(=O)CN=C1C1=CC=CC=C1 IVUAAOBNUNMJQC-UHFFFAOYSA-N 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- IIMORJBKKQKUHH-UHFFFAOYSA-N BrC=1C=CC2=C(C(=[N+](CC(N2)=O)[O-])C2=CC=C(C=C2)Cl)C1 Chemical compound BrC=1C=CC2=C(C(=[N+](CC(N2)=O)[O-])C2=CC=C(C=C2)Cl)C1 IIMORJBKKQKUHH-UHFFFAOYSA-N 0.000 description 1
- UJHVWWYDSASWAY-UHFFFAOYSA-N CHEMBL60665 Chemical compound C12=CC=CC=C2NC(=O)C[N+]([O-])=C1C1=CC=CC=C1 UJHVWWYDSASWAY-UHFFFAOYSA-N 0.000 description 1
- 210000003169 Central Nervous System Anatomy 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 210000003205 Muscles Anatomy 0.000 description 1
- NKYPEFVUOPDNPU-UHFFFAOYSA-N [7-bromo-5-(4-chlorophenyl)-2-oxo-1,3-dihydro-1,4-benzodiazepin-3-yl] acetate Chemical compound C12=CC(Br)=CC=C2NC(=O)C(OC(=O)C)N=C1C1=CC=C(Cl)C=C1 NKYPEFVUOPDNPU-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000001773 anti-convulsant Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000001624 sedative Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 230000002936 tranquilizing Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
Description
Die Erfindung betrifft ein Verfahren zur Herstellung von S-Acyloxy-SH-UI-dihydro-l^-benzodiazepin-2-on-derivaten der allgemeinen Formel IThe invention relates to a process for the preparation of S-acyloxy-SH-UI-dihydro-l ^ -benzodiazepin-2-one derivatives of the general formula I.
N-CO-N-CO-
CH-OR' ICH-OR 'I
ArAr
in der X und Y Wasserstoff-^Chlör- oder-Bromatome, die Nitro-, Trifluormethyl^oder Methylsulfonylgruppe, R ein. Wasserstoffatom, einen niedermolekularen Alkylrest, z. B. Methyl, Äthyl oder Propyl, Alkenylrest, wie Allyl oder Methallyl, oder Aralkylrest, z. B. Benzyl oder Phenäthyl, R' einen Acyl- oder Halogenacylrest und Ar einen unsubstituierten oder durch ein Chloroder Fluoratom oder durch eine Methoxy^ Methyloder Trifiuormethylgruppe substituierten Phenylrest oder einen Thienylrest bedeutet.in which X and Y hydrogen, chlorine or bromine atoms, the nitro, trifluoromethyl ^ or methylsulfonyl group, Pure. Hydrogen atom, a low molecular weight alkyl radical, e.g. B. methyl, ethyl or propyl, alkenyl radical, such as allyl or methallyl, or aralkyl radical, e.g. B. benzyl or phenethyl, R 'is an acyl or haloacyl radical and Ar is an unsubstituted or by a chlorine or fluorine atom or by a methoxy ^ methyl or Trifluoromethyl group-substituted phenyl radical or a thienyl radical.
Als Acylreste können z. B. genannt werden Acetyl, Propionyl, Caproyl, Benzoyl, Toluyl, Phenylacetyl, /3-Phenylpropionyl und Cinnamoyl, oder Halogencarbonsäure-acylreste wie Chloracetyl, Chlorbenzoyl oder Brombenzoyl.As acyl radicals, for. B. acetyl, propionyl, caproyl, benzoyl, toluyl, phenylacetyl, / 3-phenylpropionyl and cinnamoyl, or halocarboxylic acid acyl radicals such as chloroacetyl, chlorobenzoyl or bromobenzoyl.
Die erfindungsgemäß hergestellten Verbindungen zeigen im allgemeinen eine wertvolle Aktivität auf das Zentralnervensystem wie antikonvulsive, sedative, Tranquilizer oder muskelentspannende Wirkung, wie in pharmakologischen Standardversuchen an Versuchstieren gezeigt werden konnte. Sie stellen außerdem nützliche Zwischenprodukte zur Herstellung anderer 3 H-ljl-Dihydro-l^-benzodiazepin-I-on-derivate dar, insbesondere zur Herstellung von 3-Hydroxyverbindungen. The compounds prepared according to the invention generally show a valuable activity on the Central nervous system such as anticonvulsant, sedative, tranquilizer or muscle relaxing effect, such as could be shown in standard pharmacological experiments on laboratory animals. They also pose useful intermediates for the preparation of other 3 H-ljl-dihydro-l ^ -benzodiazepin-I-one derivatives represent, in particular for the production of 3-hydroxy compounds.
überraschenderweise wurde gefunden, daß die Herstellung der Verbindungen der allgemeinen Formel I erfindungsgemäß in hohen Ausbeuten dadurch gelingt, daß man SH-l^-Dihydro-l^benzodiazepin-2-on-4-oxyd-derivat der allgemeinen Formel II 150 ecm Acetanhydrid wurde unter Umrühren lange auf dem Dampfbad erwärmt, bis sich a Feststoff aufgelöst hatte. Nach dem Abkühlen wurc 9,8 g kristallines, analytisch reines 3-Acetoxy-7-ch! 1,2 - dihydro - 5 - phenyl - 3 H -1.4 - benzodiazepin - 2 Schmp. 242 bis 243° C, abfiltriert.Surprisingly, it has been found that the preparation of the compounds of the general formula I according to the invention succeeds in high yields by using SH-l ^ -dihydro-l ^ benzodiazepin-2-one-4-oxide derivative of the general formula II 150 ecm acetic anhydride was added with stirring Long warmed on the steam bath until a solid had dissolved. After cooling, worc 9.8 g of crystalline, analytically pure 3-acetoxy-7-ch! 1,2 - dihydro - 5 - phenyl - 3 H -1.4 - benzodiazepine - 2 m.p. 242 to 243 ° C, filtered off.
Analyse: Q7H13ClN2O3.Analysis: Q 7 H 13 ClN 2 O 3 .
Berechnet ... C 62,09, H 3,98, N 8,52%; gefunden ... C 62,06, H 4,13, N 8,30%.Calculated ... C 62.09, H 3.98, N 8.52%; Found ... C 62.06, H 4.13, N 8.30%.
... B e i s ρ i e 1 2... B e i s ρ i e 1 2
3,2 g 7 - Chlor - 3 - (α - chloracetoxy) -1,2 - dihyci 5-phenyl-3H-l,4-benzodiazepin-2-on wurde du. Umsetzen von Chloracetylchlorid mit 5,0 g '7-Chl 1,2 - dihydro - 5 - phenyl - 3 H -1,4 - benzodiazepin - 2 - · 4-oxyd hergestellt.3.2 g of 7-chloro-3 - (α-chloroacetoxy) -1,2-dihyci 5-phenyl-3H-1,4-benzodiazepin-2-one was du. Reaction of chloroacetyl chloride with 5.0 g of '7-Chl 1,2 - dihydro - 5 - phenyl - 3 H -1,4 - benzodiazepine - 2 - · 4-oxide produced.
Analyse: C17H12Cl2N2O3.Analysis: C 17 H 12 Cl 2 N 2 O 3 .
Berechnet ... C 56,06, H 3,32, N 7,70, Cl 19,47 gefunden ... C 56,08, H 3,42, N 7,43, Cl 19,40Calculated ... C 56.06, H 3.32, N 7.70, Cl 19.47 found ... C 56.08, H 3.42, N 7.43, Cl 19.40
CH,CH,
IIII
in der X, Y, R und Ar die oben angegebene Bedeutung besitzen, mit einem Carbonsäureanhydrid oder Car-..bonsäurehalogenid der allgemeinen Formel Z — R', in der Z den Rest O —R' oder ein Halogenatom bedeutet und R' die oben angegebene Bedeutung hat, gelinde erwärmt.in which X, Y, R and Ar have the meaning given above, with a carboxylic acid anhydride or carboxylic acid halide of the general formula Z - R ', in which Z is the radical O - R' or a halogen atom means and R 'has the meaning given above, heated gently.
Wenn das angewandte Reagens ein Carbonsäurehalogenid darstellt, besteht das Reaktionsprodukt gewöhnlich aus einem Gemisch aus vorwiegend einem hdMbdiiIf the reagent employed is a carboxylic acid halide, the reaction product will exist usually from a mixture of predominantly one hdMbdii
derivat und einer geringeren Menge eines 3-HaIogen-3 H -1,2 - dihydro -1,4 - benzodiazepin - 2 - on - derivats.derivative and a smaller amount of a 3-halogen-3 H -1,2-dihydro -1,4-benzodiazepin-2-one derivative.
Die folgenden Beispiele erläutern die Erfindung.The following examples illustrate the invention.
Eine Suspension von 10 g 7-Chlor-l,2-dihydro-5 - phenyl - 3 H -1,4 - benzodiazepin - 2 - on - 4 - oxyd inA suspension of 10 g of 7-chloro-1,2-dihydro-5-phenyl-3 H-1,4-benzodiazepine-2-one-4-oxide in
B e i s ρ i el 3B e i s ρ i el 3
Eine Suspension von 5,0 g 7-Chlor-1.2-dihyd 5 - phenyl - 3 H -1,4 - benzodiazepin - 2 - on - 4 - oxyd 20 ecm Benzoylchlorid wurde so lange erwärmt, sich aller Feststoff aufgelöst hatte. Auf Zugabe \ Cyclohexan fiel ein fester Niederschlag aus, der warmem Äthanol suspendiert wurde. Daraus wurc 1,8 g weißes kristallines 3-Benzoxy-7-chlor-l,2-di dro-5-phenyl-3H-l,4-benzodiazepin-2-on, Schmp.. bis 252° C, gewonnen.A suspension of 5.0 g of 7-chloro-1,2-dihyd 5-phenyl-3 H-1,4-benzodiazepine-2-one-4-oxide 20 ecm of benzoyl chloride was heated for so long all solids had dissolved. On the addition of cyclohexane, a solid precipitate separated out warm ethanol was suspended. This gave 1.8 g of white crystalline 3-benzoxy-7-chloro-1,2-di dro-5-phenyl-3H-1,4-benzodiazepin-2-one, m.p. to 252 ° C., obtained.
Analyse: C22H15ClN2O3.Analysis: C 22 H 15 ClN 2 O 3 .
Berechnet ... C 67,63, H 3,87, N 7,17, Cl 9,07 gefunden ... C 67,57, H 4,05, N 6,93, Cl 9,05Calculated ... C 67.63, H 3.87, N 7.17, Cl 9.07 found ... C 67.57, H 4.05, N 6.93, Cl 9.05
1,3 g 3-Acetoxy-7-chlor-5-(o-chlorphenyl)-l,2-1.3 g of 3-acetoxy-7-chloro-5- (o-chlorophenyl) -l, 2-
hydro - 3 H -1,4 - benzodiazepin - 2 - on, Schmp. 262 264° C, wurde nach dem Verfahren gemäß Beispn aus 2,6 g -7-Chlor-5-(o-chlorphenyl)- 1,2-dihyd 3 H - 1,4 - benzodiazepin - 2 - on - 4 - oxyd hergestchydro - 3 H -1,4 - benzodiazepin - 2 - one, melting point 262 264 ° C, was prepared from 2.6 g -7-chloro-5- (o-chlorophenyl) -1,2- by the method according to Example dihyd 3 H - 1,4 - benzodiazepine - 2 - one - 4 - oxide produced
' Analyse: C17H12Cl2N2O3.Analysis: C 17 H 12 Cl 2 N 2 O 3 .
Berechnet... C 56,21, H 3,33, N 7,71%; gefunden ... C 56,21, H 3,54, N 7,40%.Calculated ... C 56.21, H 3.33, N 7.71%; found ... C 56.21, H 3.54, N 7.40%.
1 g 3-Acetoxy-l,2-dihydro-5-phenyI-3H-1.4-ber.
diazepin-2-on vom Schmelzpunkt 229 bis 23 Γ C wu aus 1,5g l,2-Dihydro-5-phenyl-3H-l,4-ber.
diazepin-2-on-4-oxyd gemäß dem Beispiel 1 besen benen Verfahren hergestellt.
Analyse: C17H14.N->03.
C 69,39, H 4,80, N 9,51%;1 g of 3-acetoxy-1,2-dihydro-5-phenyI-3H-1.4-ber. diazepin-2-one with a melting point of 229 to 23 ° C was obtained from 1.5g of 1,2-dihydro-5-phenyl-3H-1,4-ber. diazepin-2-one-4-oxide prepared according to Example 1 besen surrounded process.
Analysis: C 17 H 14 .N-> 0 3 .
C 69.39, H 4.80, N 9.51%;
Berechnet
gefundenCalculated
found
C 69,30, H 4,91, N 9,64%.C 69.30, H 4.91, N 9.64%.
1,1 g 3-Acetoxy-7-chlor-1.2-dihydro-l-meti 5-phenyl-3H-l,4-'benzodiazepin-2-on vom Schm punkt 262 bis 263° C wurde aus 1.0 g 7-Chlor-U1.1 g of 3-acetoxy-7-chloro-1,2-dihydro-l-meti 5-phenyl-3H-1,4-'benzodiazepin-2-one from Schm point 262 to 263 ° C, 1.0 g of 7-chloro-U
j hydro -1 - methyl - 5 - phenyl - 3 H -1,4 - benzodiazepin-j hydro -1 - methyl - 5 - phenyl - 3 H -1,4 - benzodiazepine
2-on-4-oxyd gemäß dem im Beispiel 1 beschriebenen2-on-4-oxide according to that described in Example 1
j Verfahren hergestellt.j procedure produced.
Analyse: C18H15ClN2O3.Analysis: C 18 H 15 ClN 2 O 3 .
Berechnet ... C 63,07, H 4,41, N 8,17, Cl 10,34%;Calculated ... C 63.07, H 4.41, N 8.17, Cl 10.34%;
: gefunden ... C 63,16, H 4,57, N 8,22, Cl 10,25%.: found ... C 63.16, H 4.57, N 8.22, Cl 10.25%.
0,3 g 3-Acetoxy-7-brom-5-(p-chlorphenyl)-l,2-dihydro-3H-l,4-benzodiazepin-2-on vom Schmelzpunkt 256 bis 257° C wurde aus 0,5 g 7-Brom-5-(p-chlorphenyl) -1,2 - dihydro - 3 H -1,4 - benzodiazepin - 2 - on-4-oxyd gemäß dem im Beispiel 1 beschriebenen Verfahren hergestellt.0.3 g of 3-acetoxy-7-bromo-5- (p-chlorophenyl) -1, 2-dihydro-3H-1,4-benzodiazepin-2-one with a melting point of 256 to 257 ° C, 0.5 g of 7-bromo-5- (p-chlorophenyl) -1,2 - dihydro - 3 H -1,4 - benzodiazepine - 2 - one-4-oxide prepared according to the method described in Example 1.
Analyse: C17H12BrClN2O3.Analysis: C 17 H 12 BrClN 2 O 3 .
Berechnet:Calculated:
C 50,07, H 2,97, N 6,86, Cl 8,70, Br 19,60%;
gefunden:C 50.07, H 2.97, N 6.86, Cl 8.70, Br 19.60%;
found:
C 50,08, H 3,08, N 6,77, Cl 8,51, Br 19,18%.C 50.08, H 3.08, N 6.77, Cl 8.51, Br 19.18%.
4 g 7-Chlor-3-(a-chloracetoxy)-l,2-dihydro-5-phenyl-3H-l',4-benzodiazepin-2-on vom Schmelzpunkt 230 bis 23 Γ C wurde aus 5 g 7-Chlor-l,2-dihydro-5 - phenyl - 3 H -1,4 - benzodiazepin - 2 - on - 4 - oxyd und a-Chloressigsäureanhydrid gemäß dem im Beispiel 1 beschriebenen Verfahren hergestellt.4 g of 7-chloro-3- (a-chloroacetoxy) -l, 2-dihydro-5-phenyl-3H-l ', 4-benzodiazepin-2-one with a melting point of 230 to 23 ° C., 5 g of 7-chloro-1,2-dihydro-5 - phenyl - 3 H -1,4 - benzodiazepine - 2 - one - 4 - oxide and α-Chloroacetic anhydride prepared according to the method described in Example 1.
Analyse: C17H12Cl2N2O3.Analysis: C 17 H 12 Cl 2 N 2 O 3 .
Berechnet ... .C 56,06, H 3,32, N 7,70, Cl 19,47%; gefunden ... C 56,08, H 3,42, N 7,43, Cl 19,40%.Calculated .... C 56.06, H 3.32, N 7.70, Cl 19.47%; Found ... C 56.08, H 3.42, N 7.43, Cl 19.40%.
Claims (1)
Family
ID=
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2519318A1 (en) * | 1974-04-30 | 1975-11-06 | Ferrer Labor | 1,4-BENZODIAZEPINE, METHOD OF MANUFACTURING AND MEDICINAL PRODUCTS CONTAINING IT |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2519318A1 (en) * | 1974-04-30 | 1975-11-06 | Ferrer Labor | 1,4-BENZODIAZEPINE, METHOD OF MANUFACTURING AND MEDICINAL PRODUCTS CONTAINING IT |
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