DE1913536C2 - 1-Phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one und Verfahren zu deren Herstellung - Google Patents
1-Phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one und Verfahren zu deren HerstellungInfo
- Publication number
- DE1913536C2 DE1913536C2 DE19691913536 DE1913536A DE1913536C2 DE 1913536 C2 DE1913536 C2 DE 1913536C2 DE 19691913536 DE19691913536 DE 19691913536 DE 1913536 A DE1913536 A DE 1913536A DE 1913536 C2 DE1913536 C2 DE 1913536C2
- Authority
- DE
- Germany
- Prior art keywords
- tetrahydro
- benzodiazepin
- phenyl
- chloro
- ones
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- JQQNQRYTUIVTJG-UHFFFAOYSA-N 5-phenyl-2,3-dihydro-1h-1,5-benzodiazepin-4-one Chemical class O=C1CCNC2=CC=CC=C2N1C1=CC=CC=C1 JQQNQRYTUIVTJG-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000002936 tranquilizing effect Effects 0.000 description 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 description 3
- 239000012433 hydrogen halide Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 206010002091 Anaesthesia Diseases 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000037005 anaesthesia Effects 0.000 description 2
- 229960004782 chlordiazepoxide Drugs 0.000 description 2
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 229960003529 diazepam Drugs 0.000 description 2
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- ADIMAYPTOBDMTL-UHFFFAOYSA-N oxazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(O)N=C1C1=CC=CC=C1 ADIMAYPTOBDMTL-UHFFFAOYSA-N 0.000 description 2
- 229960004535 oxazepam Drugs 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003204 tranquilizing agent Substances 0.000 description 2
- HCDXLUKTYFLIEM-UHFFFAOYSA-N 1,2-benzodiazepin-5-one Chemical compound O=C1C=CN=NC2=CC=CC=C12 HCDXLUKTYFLIEM-UHFFFAOYSA-N 0.000 description 1
- ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical class N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 description 1
- -1 3 - chloropropionylamino Chemical group 0.000 description 1
- INUNLMUAPJVRME-UHFFFAOYSA-N 3-chloropropanoyl chloride Chemical compound ClCCC(Cl)=O INUNLMUAPJVRME-UHFFFAOYSA-N 0.000 description 1
- QNFJZHLDPYFIMJ-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-1-methyl-2,3-dihydro-1,5-benzodiazepin-4-one Chemical compound C12=CC(Cl)=CC=C2N(C)CCC(=O)N1C1=CC=CC=C1Cl QNFJZHLDPYFIMJ-UHFFFAOYSA-N 0.000 description 1
- IWQVRMPFEMZTAK-UHFFFAOYSA-N 7-chloro-5-(4-chlorophenyl)-2,3-dihydro-1h-1,5-benzodiazepin-4-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)CCNC2=CC=C(Cl)C=C21 IWQVRMPFEMZTAK-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 206010021118 Hypotonia 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
- 241000699673 Mesocricetus auratus Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000036640 muscle relaxation Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000028527 righting reflex Effects 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229940125725 tranquilizer Drugs 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
- C07D243/12—1,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
R2 | LD50 | 7νλ) | Tran. | 1,3 | III | Musk. | 48 | Pent. | Hexob. | VII | VIII | |
mg/kg | 2300 | ED50 | 21 | (1:11) | EOn | 108 | ED«, | EDj-fech | (IV: V) | (VI: V) | ||
p.o. | >5000 | mg/kg | 31,6 | 590 | mg/kg | >640 | mg/kg | mg/kg | 8 | 10,8 | ||
I | 1500 | p.o. | 14,3 | 109 | p.o. | >640 | p.o. | p.o. | 39 | 11 | ||
2000 | II | 1,6 | > 160 | IV | 64 | V | VI | 32 | 4,3 | |||
5300 | 9,3 | 105 | . >640 | >53 | 6,7 | |||||||
H | 3500 | 2,8 | 1250 | 350 | 6,0 | 65 | 7,7 | 5,4 | ||||
2-Cl | >5000 | 9,5 | 570 | 350 | 2,8 | 30 | > 103 | 10,5 | ||||
3-Cl | >5000 | 15,6 | 1150 | >640 | 20 | 85 | 64 | 2,7 | ||||
4-Cl | 2100 | 7,6 | >53O | 26 | 12 | 80 | 54 | 11,5 | ||||
R1 | H | 780 | 7,3 | >320 | 33 | 8,3 | 45 | >80 | 4,4 | |||
' 2-CI | 140C | 276 | 1,5 | 6,2 | 65 | 11 | 3,1 | |||||
2-Cl | >5000 | 107 | 3,0 | 5,5 | 15 | 6,6 | 2,0 | |||||
H | 6,5 | 75 | 2,5 | 1,6 | ||||||||
2-Cl | 8,0 | 35 | 1,7 | 1,1 | ||||||||
H | 8,0 | 25 | ||||||||||
H | 5,0 | 10 | ||||||||||
H | 0,6 | 1,0 | ||||||||||
H | 1,8 | 2,0 | ||||||||||
H | ||||||||||||
I CH3 | ||||||||||||
I C2H5 | ||||||||||||
I C3H7 | ||||||||||||
I CHj-CH = CH2 | ||||||||||||
A CHj-CH = CH2 | ||||||||||||
I CH2-C-CH | ||||||||||||
Β Chlordiazepoxid | ||||||||||||
§ Diazepam | ||||||||||||
Oxazepam |
Fp = 183 -184° C (aus Methanol)
Claims (2)
Priority Applications (23)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19691913536 DE1913536C2 (de) | 1969-03-18 | 1969-03-18 | 1-Phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one und Verfahren zu deren Herstellung |
GB01080/70A GB1279915A (en) | 1969-03-18 | 1970-03-09 | 0-aryl-2,3,4,5-tetrahydro-1h-1,5-benzodiazepine-2-ones and a process for their preparation |
IL34044A IL34044A (en) | 1969-03-18 | 1970-03-10 | 1-phenyl-2,3,4,5-tetrahydro-1h-1,5-benzodiazepin-2-one derivatives,process for their preparation and pharmaceutical compositions containing them |
CS1650A CS161871B2 (de) | 1969-03-18 | 1970-03-12 | |
FR7009086A FR2038904A5 (de) | 1969-03-18 | 1970-03-13 | |
IE335/70A IE33750B1 (en) | 1969-03-18 | 1970-03-13 | 1-aryl-2,3,4,5-tetrahydro-1h-1,5-benzodiazepine-2-ones and a process for their preparation |
AT243970A AT296994B (de) | 1969-03-18 | 1970-03-16 | Verfahren zur Herstellung von neuen 1-Aryl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-onen |
SU1415068A SU400100A1 (ru) | 1970-03-16 | Способ получения производных бензодиазепина | |
BE747400D BE747400A (fr) | 1969-03-18 | 1970-03-16 | Derives de benzodiazepine |
CH387470A CH533629A (de) | 1969-03-18 | 1970-03-16 | Verfahren zur Herstellung von Benzodiazepinderivaten |
BR21747470A BR7017474D0 (pt) | 1969-03-18 | 1970-03-16 | Processo para obtencao de derivados de benzodiazepina |
ES377621A ES377621A1 (es) | 1969-03-18 | 1970-03-17 | Procedimiento para la obtencion de derivados de benzodiace-pina. |
NO0968/70A NO125314B (de) | 1969-03-18 | 1970-03-17 | |
DK132070AA DK127784B (da) | 1969-03-18 | 1970-03-17 | Fremgangsmåde til fremstilling af 1-aryl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-oner. |
FI700738A FI49964C (fi) | 1969-03-18 | 1970-03-17 | Tapa valmistaa terapeuttisesti käytettäviä substituoituja 1-fenyyli-2, 3,4,5-tetrahydro-1H-1,5-bensodiatsepiini-2-oneja. |
BG014206A BG17601A3 (bg) | 1969-03-18 | 1970-03-17 | Метод за получаане на нови бензодиазепанови производни |
YU662/70A YU33790B (en) | 1969-03-18 | 1970-03-17 | Process for preparing 1-phenyl-2,3,4,5-tetrahydro-1h-1,5-benzodiazepine-2-ones |
SE03653/70A SE357366B (de) | 1969-03-18 | 1970-03-18 | |
NL7003883.A NL166935C (nl) | 1969-03-18 | 1970-03-18 | Werkwijze voor het bereiden van kalmerend werkzame benzodiazepinonen, alsmede werkwijze ter bereiding van farmaceutische preparaten met daarin de aldus bereide verbindingen. |
PH11246A PH10103A (en) | 1969-03-18 | 1970-03-18 | 1)aryl-2,3,4,5-tetrahydro-1h-1,5-benzodiazepin 2-ones derivatives,its pharmaceutical composition and process of preparation |
US05/765,696 US4108852A (en) | 1969-03-18 | 1977-02-04 | Process for preparing 1,5-benzodiazepine-2-ones |
US05/911,831 US4239684A (en) | 1969-03-18 | 1978-06-02 | 1,5'-Benzodiazepine-2-ones, pharmaceutical compositions thereof and method of use thereof |
US06/031,589 USRE30293E (en) | 1969-03-18 | 1979-04-19 | Process for preparing 1,5-benzodiazepine-2-ones |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19691913536 DE1913536C2 (de) | 1969-03-18 | 1969-03-18 | 1-Phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one und Verfahren zu deren Herstellung |
Publications (2)
Publication Number | Publication Date |
---|---|
DE1913536A1 DE1913536A1 (de) | 1970-10-01 |
DE1913536C2 true DE1913536C2 (de) | 1983-05-11 |
Family
ID=5728408
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19691913536 Expired DE1913536C2 (de) | 1969-03-18 | 1969-03-18 | 1-Phenyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one und Verfahren zu deren Herstellung |
Country Status (2)
Country | Link |
---|---|
BR (1) | BR7017474D0 (de) |
DE (1) | DE1913536C2 (de) |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1670190A1 (de) * | 1967-02-07 | 1970-12-03 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von 1,5-Dihydro-5-phenyl-3H-1,5-benzodiazepin-2,4-dionen |
-
1969
- 1969-03-18 DE DE19691913536 patent/DE1913536C2/de not_active Expired
-
1970
- 1970-03-16 BR BR21747470A patent/BR7017474D0/pt unknown
Also Published As
Publication number | Publication date |
---|---|
DE1913536A1 (de) | 1970-10-01 |
BR7017474D0 (pt) | 1973-02-13 |
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