DD152936A5 - Verfahren zur herstellung von neuen 4-aryl-5,6-7,8-tetrahydropyrazolo(3,4-b)diazepin-1h,4h-5,7-dionen und diese enthaltende arzneimittel - Google Patents

Verfahren zur herstellung von neuen 4-aryl-5,6-7,8-tetrahydropyrazolo(3,4-b)diazepin-1h,4h-5,7-dionen und diese enthaltende arzneimittel Download PDF

Info

Publication number: DD152936A5
Authority: DD; German Democratic Republic
Prior art keywords: group; dione; tetrahydropyrazolo; diazepine; atoms
Prior art date: 1979-08-14

Application number

DD80223270A

Other languages

German (de)

English (en)

Inventor

Gerhard Rackur

Irmgard Hoffmann

Original Assignee

Hoechst Ag

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.)

1979-08-14

Filing date

1980-08-12

Publication date

1981-12-16

1980-08-12 Application filed by Hoechst Ag filed Critical Hoechst Ag

1981-12-16 Publication of DD152936A5 publication Critical patent/DD152936A5/de

Links

239000003814 drug Substances 0.000 title abstract description 6
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 45
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
238000000034 method Methods 0.000 claims abstract description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
238000002360 preparation method Methods 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
229910052794 bromium Inorganic materials 0.000 claims abstract description 6
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
125000003118 aryl group Chemical group 0.000 claims abstract description 4
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
239000000460 chlorine Substances 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 2
-1 2-methylsulfonylethyl Chemical group 0.000 description 24
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 14
239000000243 solution Substances 0.000 description 14
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
125000001309 chloro group Chemical group Cl* 0.000 description 11
239000012442 inert solvent Substances 0.000 description 10
239000002904 solvent Substances 0.000 description 10
POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000000203 mixture Substances 0.000 description 7
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 6
230000000144 pharmacologic effect Effects 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
230000000949 anxiolytic effect Effects 0.000 description 5
125000004104 aryloxy group Chemical group 0.000 description 5
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000007858 starting material Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 4
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
239000000370 acceptor Substances 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
230000001476 alcoholic effect Effects 0.000 description 4
239000002249 anxiolytic agent Substances 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
125000004423 acyloxy group Chemical group 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000013078 crystal Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
230000001624 sedative effect Effects 0.000 description 3
239000011734 sodium Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 2
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 2
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
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 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000013543 active substance Substances 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
125000003282 alkyl amino group Chemical group 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
230000002082 anti-convulsion Effects 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
150000001502 aryl halides Chemical class 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
125000000751 azo group Chemical group [*]N=N[*] 0.000 description 2
229940049706 benzodiazepine Drugs 0.000 description 2
150000001557 benzodiazepines Chemical class 0.000 description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
GNEVIACKFGQMHB-UHFFFAOYSA-N carbon suboxide Chemical compound O=C=C=C=O GNEVIACKFGQMHB-UHFFFAOYSA-N 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
235000013601 eggs Nutrition 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
150000002690 malonic acid derivatives Chemical class 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
230000001777 nootropic effect Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
150000007530 organic bases Chemical group 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
229960004526 piracetam Drugs 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229920000137 polyphosphoric acid Polymers 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
235000011056 potassium acetate Nutrition 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
FSWUGFSHWYDKTO-UHFFFAOYSA-N 1-ethyl-3-methylpyrazole Chemical compound CCN1C=CC(C)=N1 FSWUGFSHWYDKTO-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
IEEHKTFVUIVORU-UHFFFAOYSA-N 2-methylpropanedioyl dichloride Chemical compound ClC(=O)C(C)C(Cl)=O IEEHKTFVUIVORU-UHFFFAOYSA-N 0.000 description 1
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
FJXXPBSXLGDGQI-UHFFFAOYSA-N 5,6-bis(2-chloroethylsulfanyl)-1h-benzimidazole-4,7-dione Chemical compound O=C1C(SCCCl)=C(SCCCl)C(=O)C2=C1N=CN2 FJXXPBSXLGDGQI-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
206010003497 Asphyxia Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
241000699800 Cricetinae Species 0.000 description 1
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
229920004449 Halon® Polymers 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
206010039897 Sedation Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
230000001741 anti-phlogistic effect Effects 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
230000037007 arousal Effects 0.000 description 1
238000006254 arylation reaction Methods 0.000 description 1
XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 1
239000002585 base Substances 0.000 description 1
CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical compound [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 description 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000007385 chemical modification Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
230000001419 dependent effect Effects 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
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
229960004279 formaldehyde Drugs 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
238000010438 heat treatment Methods 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
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
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
206010022437 insomnia Diseases 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000015110 jellies Nutrition 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
230000037023 motor activity Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229960005152 pentetrazol Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000006894 reductive elimination reaction Methods 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
231100000241 scar Toxicity 0.000 description 1
230000007017 scission Effects 0.000 description 1
230000036280 sedation Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000010998 test method Methods 0.000 description 1
125000003396 thiol group Chemical group [H]S* 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
125000001701 trimethoxybenzyl group Chemical group 0.000 description 1
VCBSMHZNRBWEIJ-UHFFFAOYSA-L trimethyl-[5-[5-(trimethylazaniumyl)pentoxy]pentyl]azanium;dichloride Chemical compound [Cl-].[Cl-].C[N+](C)(C)CCCCCOCCCCC[N+](C)(C)C VCBSMHZNRBWEIJ-UHFFFAOYSA-L 0.000 description 1
238000001665 trituration Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom
- 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)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Anesthesiology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biomedical Technology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DD80223270A 1979-08-14 1980-08-12 Verfahren zur herstellung von neuen 4-aryl-5,6-7,8-tetrahydropyrazolo(3,4-b)diazepin-1h,4h-5,7-dionen und diese enthaltende arzneimittel DD152936A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19792932835 DE2932835A1 (de)	1979-08-14	1979-08-14	Neue 4-aryl-5,6,7,8-tetrahydropyrazolo(3,4-b)diazepin-1h,4h-5,7-dione und verfahren zu ihrer darstellung

Publications (1)

Publication Number	Publication Date
DD152936A5 true DD152936A5 (de)	1981-12-16

Family

ID=6078398

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
DD80223270A DD152936A5 (de)	1979-08-14	1980-08-12	Verfahren zur herstellung von neuen 4-aryl-5,6-7,8-tetrahydropyrazolo(3,4-b)diazepin-1h,4h-5,7-dionen und diese enthaltende arzneimittel
DD80230827A DD159699A5 (de)	1979-08-14	1980-08-12	Verfahren zur herstellung von 4-aryl-5,6,7,7-tetrahydropyrazolo (3,4b) (1,5)-diazepin-1h,4h-5,7-dione enthaltenden arzneimitteln
DD81230731A DD159640A5 (de)	1979-08-14	1981-06-11	Verfahren zur herstellung von 5,6,7,8-tetrahydropyrazolo-(3,4 b)(1,5)-diazepin-1h,4h-5,7-dionen

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
DD80230827A DD159699A5 (de)	1979-08-14	1980-08-12	Verfahren zur herstellung von 4-aryl-5,6,7,7-tetrahydropyrazolo (3,4b) (1,5)-diazepin-1h,4h-5,7-dione enthaltenden arzneimitteln
DD81230731A DD159640A5 (de)	1979-08-14	1981-06-11	Verfahren zur herstellung von 5,6,7,8-tetrahydropyrazolo-(3,4 b)(1,5)-diazepin-1h,4h-5,7-dionen

Country Status (21)

Country	Link
US (1)	US4302468A (cs)
EP (2)	EP0050376B1 (cs)
JP (1)	JPS5630977A (cs)
AR (1)	AR226860A1 (cs)
AT (2)	ATE5536T1 (cs)
AU (1)	AU535884B2 (cs)
CA (1)	CA1151645A (cs)
CS (4)	CS223833B2 (cs)
DD (3)	DD152936A5 (cs)
DE (3)	DE2932835A1 (cs)
DK (1)	DK350180A (cs)
ES (4)	ES8103747A1 (cs)
FI (1)	FI802536A7 (cs)
GR (1)	GR69798B (cs)
HU (1)	HU180163B (cs)
IL (1)	IL60828A (cs)
NO (1)	NO802425L (cs)
NZ (1)	NZ194633A (cs)
PH (1)	PH18209A (cs)
PT (1)	PT71692B (cs)
ZA (1)	ZA804959B (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5198436A (en) *	1989-10-17	1993-03-30	Ellinwood Jr Everett H	Intraoral dosing method of administering trifluorobenzodiazepines

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3558605A (en) *	1969-05-14	1971-01-26	Parke Davis & Co	Pyrazolo(3,4-e)(1,4)diazepin-7-(1h)-one compounds
AT325052B (de) *	1972-12-07	1975-10-10	Degussa	Verfahren zur herstellung von neuen 6-azabenzo-1,5-diazepinen und ihren salzen

1979
- 1979-08-14 DE DE19792932835 patent/DE2932835A1/de not_active Withdrawn
1980
- 1980-08-07 DE DE8080104654T patent/DE3062746D1/de not_active Expired
- 1980-08-07 EP EP81110770A patent/EP0050376B1/de not_active Expired
- 1980-08-07 DE DE8181110770T patent/DE2966484D1/de not_active Expired
- 1980-08-07 EP EP80104654A patent/EP0024038B1/de not_active Expired
- 1980-08-07 AT AT81110770T patent/ATE5536T1/de not_active IP Right Cessation
- 1980-08-07 AT AT80104654T patent/ATE3040T1/de not_active IP Right Cessation
- 1980-08-08 ES ES494142A patent/ES8103747A1/es not_active Expired
- 1980-08-08 ES ES494143A patent/ES494143A0/es active Granted
- 1980-08-08 ES ES494141A patent/ES494141A0/es active Granted
- 1980-08-08 ES ES494144A patent/ES494144A0/es active Granted
- 1980-08-12 DD DD80223270A patent/DD152936A5/de unknown
- 1980-08-12 FI FI802536A patent/FI802536A7/fi not_active Application Discontinuation
- 1980-08-12 PH PH24435A patent/PH18209A/en unknown
- 1980-08-12 US US06/177,411 patent/US4302468A/en not_active Expired - Lifetime
- 1980-08-12 PT PT71692A patent/PT71692B/pt unknown
- 1980-08-12 GR GR62647A patent/GR69798B/el unknown
- 1980-08-12 AR AR282129A patent/AR226860A1/es active
- 1980-08-12 IL IL60828A patent/IL60828A/xx unknown
- 1980-08-12 DD DD80230827A patent/DD159699A5/de unknown
- 1980-08-12 NZ NZ194633A patent/NZ194633A/xx unknown
- 1980-08-13 NO NO802425A patent/NO802425L/no unknown
- 1980-08-13 CS CS805580A patent/CS223833B2/cs unknown
- 1980-08-13 DK DK350180A patent/DK350180A/da not_active Application Discontinuation
- 1980-08-13 ZA ZA00804959A patent/ZA804959B/xx unknown
- 1980-08-13 CA CA000358165A patent/CA1151645A/en not_active Expired
- 1980-08-13 CS CS817964A patent/CS223845B2/cs unknown
- 1980-08-13 CS CS817966A patent/CS223847B2/cs unknown
- 1980-08-13 AU AU61423/80A patent/AU535884B2/en not_active Ceased
- 1980-08-13 CS CS817965A patent/CS223846B2/cs unknown
- 1980-08-13 HU HU80802017A patent/HU180163B/hu unknown
- 1980-08-14 JP JP11225480A patent/JPS5630977A/ja active Pending
1981
- 1981-06-11 DD DD81230731A patent/DD159640A5/de unknown

Also Published As

Publication number	Publication date
CS223833B2 (en)	1983-11-25
CS223846B2 (en)	1983-11-25
EP0024038A3 (en)	1981-04-15
NO802425L (no)	1981-02-16
HU180163B (en)	1983-02-28
DD159640A5 (de)	1983-03-23
DE2966484D1 (en)	1984-01-12
IL60828A0 (en)	1980-10-26
DD159699A5 (de)	1983-03-30
ZA804959B (en)	1981-08-26
AU6142380A (en)	1981-02-19
AU535884B2 (en)	1984-04-12
JPS5630977A (en)	1981-03-28
FI802536A7 (fi)	1981-01-01
PT71692A (de)	1980-09-01
ES8103748A1 (es)	1981-03-16
DE3062746D1 (en)	1983-05-19
ES494142A0 (es)	1981-03-16
ES8103749A1 (es)	1981-03-16
DE2932835A1 (de)	1981-03-26
ES494143A0 (es)	1981-03-16
NZ194633A (en)	1982-03-23
DK350180A (da)	1981-02-15
ES8103746A1 (es)	1981-03-16
AR226860A1 (es)	1982-08-31
ES8103747A1 (es)	1981-03-16
CA1151645A (en)	1983-08-09
EP0050376B1 (de)	1983-12-07
CS223847B2 (en)	1983-11-25
GR69798B (cs)	1982-07-12
ES494144A0 (es)	1981-03-16
EP0050376A1 (de)	1982-04-28
CS223845B2 (en)	1983-11-25
EP0024038A2 (de)	1981-02-18
PH18209A (en)	1985-04-30
ES494141A0 (es)	1981-03-16
PT71692B (de)	1982-01-22
IL60828A (en)	1984-04-30
EP0024038B1 (de)	1983-04-13
US4302468A (en)	1981-11-24
ATE5536T1 (de)	1983-12-15
ATE3040T1 (de)	1983-04-15

Publication	Publication Date	Title
DE69603240T2 (de)	2000-01-05	Neue deazapurinderivate; eine neue klasse von crf1-spezifischen liganden
DE2609486C2 (cs)	1988-11-03
EP0059390A1 (de)	1982-09-08	Imidazodiazepine, Zwischenprodukte und Verfahren für ihre Herstellung, sowie diese enthaltende Arzneimittel
EP0022078A1 (de)	1981-01-07	Pyrazolochinoline, Verfahren zu ihrer Herstellung, und pharmazeutische Präparate enthaltend diese Verbindungen
EP0288431B1 (de)	1992-08-19	3H-1,2,3-Triazolo[4,5-d]pyrimidine
DD153692A5 (de)	1982-01-27	Verfahren zur herstellung von benzodiazepinverbindungen
EP0180115A2 (de)	1986-05-07	1,2,4-Triazolo-carbamate und ihre Säureadditionssalze, Verfahren zu ihrer Herstellung und Arzneimittel
NO126085B (cs)	1972-12-18
DD152936A5 (de)	1981-12-16	Verfahren zur herstellung von neuen 4-aryl-5,6-7,8-tetrahydropyrazolo(3,4-b)diazepin-1h,4h-5,7-dionen und diese enthaltende arzneimittel
EP0059388B1 (de)	1985-05-29	Imidazodiazepine, Verfahren und Zwischenprodukte zu deren Herstellung, sowie diese enthaltende Arzneimittel
DE2539114A1 (de)	1976-03-25	7-substituierte 3-(aminomethyl)- 3,5-dihydro-as-triazino eckige klammer auf 4,3-a eckige klammer zu eckige klammer auf 1,4 eckige klammer zu benzodiazepin-2-(1h)-one und ein verfahren zu deren herstellung
DE2242059A1 (de)	1973-03-15	2,4-dihydro-1h-s-triazolo eckige klammer auf 4,3-a eckige klammer zu eckige klammer auf 1,4 eckige klammer zu benzodiazepine und verfahren zu ihrer herstellung
DE2906401A1 (de)	1980-09-04	8-aryl-5,6-7,8-tetrahydropyrazolo (3,4-b)(1,5)diazepin-1h,4h-5,7-dione und verfahren zu ihrer darstellung
DE2233682A1 (de)	1973-10-11	2- eckige klammer auf 3-(subst. aminomethyl)-4-h-1,2,4-triazol-4-yl eckige klammer zu -benzophenone, ein verfahren zu ihrer herstellung sowie diese enthaltende arzneimittel
DE2308280A1 (de)	1973-09-06	Verfahren zur herstellung von neuen diazepinderivaten
DD201789A5 (de)	1983-08-10	Verfahren zur herstellung von 2-acylaminomethyl-1,4-benzodiazepinen
DE2446495A1 (de)	1975-04-10	Neue pyrazolo(3,4-b)thieno(2,3-d) pyridin-2-carboxylsaeuren und -saeureester
DE2410030C3 (de)	1982-11-11	8-Brom-6-phenyl-4H-s-triazolo[3,4-c]thieno[2,3-e]1,4-diazepine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
EP0195939B1 (de)	1991-06-12	Imidazodiazepin-Derivate
DE2700539A1 (de)	1977-08-11	Benzodiazepine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
DE2445430C3 (cs)	1979-01-18
DE2222068A1 (de)	1972-11-23	1,6-Disubstituierte 4H-s-Triazolo[4,3-a][1,4]-benzodiazepine,deren Saeureadditionssalze und N-Oxide,sowie Verfahren zu ihrer Herstellung
DE2460776C2 (de)	1982-12-09	1-substituierte 6-Aryl-4H-s-triazolo-(3,4c)-thieno-(2,3e)-1,4-diazepine, Verfahren zu ihrer Herstellung, diese enthaltende pharmazeutische Präparate sowie Zwischenprodukte und Verfahren zur Herstellung dieser Zwischenprodukte
KR840000991B1 (ko)	1984-07-13	이미다조 디아제핀 유도체의 제조방법
DE2257627A1 (de)	1973-07-12	4-(2-benzoylphenyl)-2,4-dihydro-5eckige klammer auf (alkylamino)-alkyl eckige klammer zu- 3h-1,2,4-triazol-3-one, deren saeureanlagerungssalze und verfahren zur herstellung dieser verbindungen