CH582183A5 - Benzodiazepine derivs useful as tranquillisers and - anti-depressants - Google Patents

Benzodiazepine derivs useful as tranquillisers and - anti-depressants

Info

Publication number: CH582183A5
Authority: CH; Switzerland
Prior art keywords: benzodiazepin; lower alkyl; phenyl; tetrahydro; group
Prior art date: 1968-08-31

Application number

CH1324469A

Other languages

German (de)

English (en)

Original Assignee

Sankyo Co

Priority date (The priority date 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 date listed.)

1968-08-31

Filing date

1969-09-01

Publication date

1976-11-30

1968-10-24 Priority claimed from JP43077503A external-priority patent/JPS4834755B1/ja

1969-09-01 Application filed by Sankyo Co filed Critical Sankyo Co

1976-11-30 Publication of CH582183A5 publication Critical patent/CH582183A5/de

Links

230000001430 anti-depressive effect Effects 0.000 title abstract description 4
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 title abstract 2
239000000935 antidepressant agent Substances 0.000 title abstract 2
229940005513 antidepressants Drugs 0.000 title abstract 2
229940049706 benzodiazepine Drugs 0.000 title abstract 2
125000000217 alkyl group Chemical group 0.000 claims abstract description 30
-1 polymethylene Polymers 0.000 claims abstract description 28
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
125000002252 acyl group Chemical group 0.000 claims abstract description 5
125000003118 aryl group Chemical group 0.000 claims abstract description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
125000004442 acylamino group Chemical group 0.000 claims abstract description 4
125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
150000003254 radicals Chemical class 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
150000002148 esters Chemical class 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 5
230000000694 effects Effects 0.000 abstract description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 abstract description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 abstract description 2
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 abstract 1
229910052736 halogen Inorganic materials 0.000 abstract 1
150000002367 halogens Chemical class 0.000 abstract 1
238000002844 melting Methods 0.000 description 58
230000008018 melting Effects 0.000 description 58
238000006243 chemical reaction Methods 0.000 description 33
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
239000002904 solvent Substances 0.000 description 20
239000013078 crystal Substances 0.000 description 19
239000000047 product Substances 0.000 description 17
150000001557 benzodiazepines Chemical class 0.000 description 15
239000000203 mixture Substances 0.000 description 15
229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 description 14
238000000354 decomposition reaction Methods 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
ROXAFEIDZVHGFX-UHFFFAOYSA-N 1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Chemical compound N1C(=O)CNCC2=CC=CC=C21 ROXAFEIDZVHGFX-UHFFFAOYSA-N 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 8
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 7
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000376 reactant Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 4
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
RFVXAEFIEWVAAF-UHFFFAOYSA-N 3-phenyl-1h-1,2-benzodiazepine Chemical class C1=CC2=CC=CC=C2NN=C1C1=CC=CC=C1 RFVXAEFIEWVAAF-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
239000004593 Epoxy Substances 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
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
238000004821 distillation Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
AKPLHCDWDRPJGD-UHFFFAOYSA-N nordazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 AKPLHCDWDRPJGD-UHFFFAOYSA-N 0.000 description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
238000003756 stirring Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
WEGOLYBUWCMMMY-UHFFFAOYSA-N 1-bromo-2-propanol Chemical compound CC(O)CBr WEGOLYBUWCMMMY-UHFFFAOYSA-N 0.000 description 2
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
SATGIBNNISQKBG-UHFFFAOYSA-N 7-chloro-3-methyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC=C2NC(=O)C(C)N=C1C1=CC=CC=C1 SATGIBNNISQKBG-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
230000002411 adverse Effects 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
230000001914 calming effect Effects 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
150000004292 cyclic ethers Chemical class 0.000 description 2
239000000284 extract Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 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
239000003960 organic solvent Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
JCERKCRUSDOWLT-UHFFFAOYSA-N 1-bromopropan-1-ol Chemical compound CCC(O)Br JCERKCRUSDOWLT-UHFFFAOYSA-N 0.000 description 1
PMHHCLXJMNLEIE-UHFFFAOYSA-N 1-iodopropan-2-ol Chemical compound CC(O)CI PMHHCLXJMNLEIE-UHFFFAOYSA-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
RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 1
SREVNOABLVPRHG-UHFFFAOYSA-N 5-phenyl-1,3,4,5-tetrahydro-1,4-benzodiazepin-2-one Chemical class C12=CC=CC=C2NC(=O)CNC1C1=CC=CC=C1 SREVNOABLVPRHG-UHFFFAOYSA-N 0.000 description 1
ZMXLAUDJKIBNLG-UHFFFAOYSA-N 7,9-dimethyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(C)=CC(C)=C2NC(=O)CN=C1C1=CC=CC=C1 ZMXLAUDJKIBNLG-UHFFFAOYSA-N 0.000 description 1
GAONFNHSQRTFJA-UHFFFAOYSA-N 7-bromo-3-methyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(Br)=CC=C2NC(=O)C(C)N=C1C1=CC=CC=C1 GAONFNHSQRTFJA-UHFFFAOYSA-N 0.000 description 1
ATCCWKYKHCKDGT-UHFFFAOYSA-N 7-bromo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(Br)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 ATCCWKYKHCKDGT-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229940072049 amyl acetate Drugs 0.000 description 1
PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 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
238000009835 boiling Methods 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
UVCOILFBWYKHHB-UHFFFAOYSA-N desalkylflurazepam Chemical compound FC1=CC=CC=C1C1=NCC(=O)NC2=CC=C(Cl)C=C12 UVCOILFBWYKHHB-UHFFFAOYSA-N 0.000 description 1
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 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000006125 ethylsulfonyl group Chemical group 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
KJONHKAYOJNZEC-UHFFFAOYSA-N nitrazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1 KJONHKAYOJNZEC-UHFFFAOYSA-N 0.000 description 1
150000003014 phosphoric acid esters Chemical class 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical group C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
239000008096 xylene Substances 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1324469A 1968-08-31 1969-09-01 Benzodiazepine derivs useful as tranquillisers and - anti-depressants CH582183A5 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP6270168		1968-08-31
JP43077503A JPS4834755B1 (es)	1968-10-24	1968-10-24

Publications (1)

Publication Number	Publication Date
CH582183A5 true CH582183A5 (en)	1976-11-30

Family

ID=26403749

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1324469A CH582183A5 (en)	1968-08-31	1969-09-01	Benzodiazepine derivs useful as tranquillisers and - anti-depressants

Country Status (5)

Country	Link
CA (1)	CA1038868A (es)
CH (1)	CH582183A5 (es)
ES (1)	ES370842A1 (es)
NL (1)	NL172658C (es)
SE (2)	SE365801B (es)

1969
- 1969-08-19 SE SE1148369A patent/SE365801B/xx unknown
- 1969-08-19 SE SE1083072A patent/SE397091B/xx unknown
- 1969-08-21 CA CA060,169A patent/CA1038868A/en not_active Expired
- 1969-08-25 ES ES370842A patent/ES370842A1/es not_active Expired
- 1969-08-29 NL NL6913216A patent/NL172658C/xx not_active IP Right Cessation
- 1969-09-01 CH CH1324469A patent/CH582183A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
NL172658B (nl)	1983-05-02
NL172658C (nl)	1983-10-03
SE365801B (es)	1974-04-01
NL6913216A (es)	1970-03-03
CA1038868A (en)	1978-09-19
ES370842A1 (es)	1971-08-01
SE397091B (sv)	1977-10-17

Legal Events

Date	Code	Title	Description
1989-11-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2265371C3 (de)	1980-12-11	N-(3-Benzoylaminopropyl)-aniline
DE2166657C2 (es)	1988-10-20
CH532065A (de)	1972-12-31	Verfahren zur Herstellung von Benzodiazepinderivaten
CH518302A (de)	1972-01-31	Verfahren zur Herstellung von Benzodiazepinderivaten
CH582183A5 (en)	1976-11-30	Benzodiazepine derivs useful as tranquillisers and - anti-depressants
CH510681A (de)	1971-07-31	Neues Verfahren zur Herstellung von 1,4-Benzodiazepinonen und deren Salzen
DE1955349C2 (de)	1982-01-28	s-Triazolo [4,3-a] [1,4] benzodiazepine
DE1290143B (de)	1969-03-06	2-Oxo-1, 2-dihydro-3H-1, 4-benzodiazepinderivate
DE2265242C2 (de)	1983-03-10	Verfahren zur Herstellung von tautomeren 4-Phenyl-1,3-dihydro-2H-1,5-benzodiazepin-2-thionen
AT274815B (de)	1969-10-10	Verfahren zur Herstellung von 1,4-Benzodiazepinen
AT237614B (de)	1964-12-28	Verfahren zur Herstellung von neuen Imidazol-Derivaten
DE1811831C3 (de)	1978-02-02	Verfahren zur Herstellung von 5-Phenyl-13-dihydro-2H-l,4-benzodiazepin-2-on-derivaten
AT256112B (de)	1967-08-10	Verfahren zur Herstellung von Benzodiazepin-Derivaten
AT311978B (de)	1973-12-10	Verfahren zur Herstellung von Benzodiazepinen bzw. von Salzen hievon
AT251588B (de)	1967-01-10	Verfahren zur Herstellung von Chinazolin-Derivaten
AT242706B (de)	1965-10-11	Verfahren zur Herstellung von neuen Benzodiazepin-Derivaten
AT276401B (de)	1969-11-25	Verfahren zur Herstellung von Benzodiazepin-Derivaten
AT239969B (de)	1965-05-10	Verfahren zur Herstellung von neuen Estern der Nicotinsäure
DE1445892C3 (de)	1976-01-22	vate
AT332876B (de)	1976-10-25	Verfahren zur herstellung von neuen benzodiazepin-derivaten
AT215996B (de)	1961-07-10	Verfahren zur Herstellung von neuen Pyridinderivaten
AT247356B (de)	1966-06-10	Verfahren zur Herstellung von neuen Benzodiazepin-Derivaten
AT264724B (de)	1968-09-10	Verfahren zur Herstellung von neuen desacetylierten mehrkernigen Indolen
AT246161B (de)	1966-04-12	Verfahren zur Herstellung von neuen Benzodiazepinderivaten
CH550810A (de)	1974-06-28	Verfahren zur herstellung von heterocyclischen verbindungen.