CH627181A5 - Process for the preparation of substituted 6-aryl-4H-s-triazolo[3,4-c]thieno[2,3-e]-1,4-diazepines - Google Patents

Process for the preparation of substituted 6-aryl-4H-s-triazolo[3,4-c]thieno[2,3-e]-1,4-diazepines Download PDF

Info

Publication number: CH627181A5
Authority: CH; Switzerland
Prior art keywords: formula; compound; vii; hydrogen; halogen
Prior art date: 1975-07-16

Application number

CH901976A

Other languages

German (de)

English (en)

Inventor

Karl-Heinz Dr Weber

Adolf Dr Bauer

Adolf Dr Langbein

Original Assignee

Boehringer Sohn Ingelheim

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.)

1975-07-16

Filing date

1976-07-14

Publication date

1981-12-31

1975-07-16 Priority claimed from DE19752531677 external-priority patent/DE2531677A1/de

1975-07-16 Priority claimed from DE2531678A external-priority patent/DE2531678C3/de

1975-07-16 Priority claimed from DE19752531679 external-priority patent/DE2531679A1/de

1975-07-30 Priority claimed from DE2533924A external-priority patent/DE2533924C3/de

1976-07-14 Application filed by Boehringer Sohn Ingelheim filed Critical Boehringer Sohn Ingelheim

1981-12-31 Publication of CH627181A5 publication Critical patent/CH627181A5/de

Links

238000000034 method Methods 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 27
239000000460 chlorine Substances 0.000 claims description 17
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
-1 sulfur halide Chemical class 0.000 claims description 7
229910021529 ammonia Inorganic materials 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
238000006356 dehydrogenation reaction Methods 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
229910052804 chromium Inorganic materials 0.000 claims description 4
239000011651 chromium Substances 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
230000003647 oxidation Effects 0.000 claims description 4
238000007254 oxidation reaction Methods 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
239000011574 phosphorus Substances 0.000 claims description 3
239000000126 substance Substances 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical group O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
239000003513 alkali Substances 0.000 claims 4
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims 2
125000002947 alkylene group Chemical group 0.000 claims 2
229910052748 manganese Inorganic materials 0.000 claims 2
239000011572 manganese Substances 0.000 claims 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
125000003585 oxepinyl group Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
ONOBXDPYDHTSBQ-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1h-diazepine Chemical compound C1CC=CCNN1 ONOBXDPYDHTSBQ-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000001773 anti-convulsant effect Effects 0.000 description 2
239000002249 anxiolytic agent Substances 0.000 description 2
230000000949 anxiolytic effect Effects 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000005457 ice water Substances 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
150000007530 organic bases Chemical group 0.000 description 2
239000012286 potassium permanganate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
KIEOKOFEPABQKJ-UHFFFAOYSA-N sodium dichromate Chemical compound [Na+].[Na+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KIEOKOFEPABQKJ-UHFFFAOYSA-N 0.000 description 2
238000003756 stirring Methods 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
CSDWGIAYTPKLRV-UHFFFAOYSA-N ClC1=CC=CC=C1C(C(N1C2)=NN2Br)=NCC(C=C2)=C1[S+]2Br Chemical compound ClC1=CC=CC=C1C(C(N1C2)=NN2Br)=NCC(C=C2)=C1[S+]2Br CSDWGIAYTPKLRV-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229910004298 SiO 2 Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
235000021050 feed intake Nutrition 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
235000010299 hexamethylene tetramine Nutrition 0.000 description 1
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
150000002697 manganese compounds Chemical class 0.000 description 1
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000000047 product Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000004575 stone Substances 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000010998 test method Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

CH901976A 1975-07-16 1976-07-14 Process for the preparation of substituted 6-aryl-4H-s-triazolo[3,4-c]thieno[2,3-e]-1,4-diazepines CH627181A5 (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE19752531677 DE2531677A1 (de)	1975-07-16	1975-07-16	Neue thieno-4,1-oxazepine und verfahren zu ihrer herstellung
DE2531678A DE2531678C3 (de)	1975-07-16	1975-07-16	Thieno [2,3e] triazole [3,4c] 5,6-dihydro-l,4diazepine und Verfahren zu ihrer Herstellung
DE19752531679 DE2531679A1 (de)	1975-07-16	1975-07-16	Neue thieno- eckige klammer auf 2,3-e eckige klammer zu -triazolo- eckige klammer auf 3,4-c eckige klammer zu -4,1-oxazepine und verfahren zu ihrer herstellung
DE2533924A DE2533924C3 (de)	1975-07-30	1975-07-30	Verfahren zur Herstellung von 6- Aryl-4H-striazolo [3,4-c] thieno [2,3-e] 1,4-diazepinen

Publications (1)

Publication Number	Publication Date
CH627181A5 true CH627181A5 (en)	1981-12-31

Family

ID=27432000

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH901976A CH627181A5 (en)	1975-07-16	1976-07-14	Process for the preparation of substituted 6-aryl-4H-s-triazolo[3,4-c]thieno[2,3-e]-1,4-diazepines
CH327381A CH630630A5 (en)	1975-07-16	1981-05-19	Processes for preparing substituted 6-aryl-4H-s-triazolo-(3,4-c)-thieno-(2,3-e)-1,4-diazepines.

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH327381A CH630630A5 (en)	1975-07-16	1981-05-19	Processes for preparing substituted 6-aryl-4H-s-triazolo-(3,4-c)-thieno-(2,3-e)-1,4-diazepines.

Country Status (17)

Country	Link
AU (1)	AU506140B2 (fr)
BG (1)	BG25227A3 (fr)
CA (1)	CA1077475A (fr)
CH (2)	CH627181A5 (fr)
DD (1)	DD126744A5 (fr)
ES (1)	ES449849A1 (fr)
FR (1)	FR2318165A1 (fr)
GR (1)	GR60819B (fr)
HU (1)	HU172620B (fr)
IE (1)	IE43694B1 (fr)
IL (1)	IL50032A (fr)
LU (1)	LU75384A1 (fr)
MX (1)	MX4246E (fr)
NL (1)	NL186008C (fr)
PT (1)	PT65374B (fr)
RO (1)	RO76083A (fr)
YU (1)	YU40458B (fr)

1976
- 1976-07-09 RO RO7686908A patent/RO76083A/fr unknown
- 1976-07-10 GR GR51234A patent/GR60819B/el unknown
- 1976-07-13 IL IL50032A patent/IL50032A/xx unknown
- 1976-07-14 LU LU75384A patent/LU75384A1/xx unknown
- 1976-07-14 DD DD193857A patent/DD126744A5/xx unknown
- 1976-07-14 CH CH901976A patent/CH627181A5/de not_active IP Right Cessation
- 1976-07-14 BG BG033745A patent/BG25227A3/xx unknown
- 1976-07-15 CA CA257,092A patent/CA1077475A/fr not_active Expired
- 1976-07-15 YU YU1753/76A patent/YU40458B/xx unknown
- 1976-07-15 AU AU15913/76A patent/AU506140B2/en not_active Expired
- 1976-07-15 NL NLAANVRAGE7607871,A patent/NL186008C/xx not_active IP Right Cessation
- 1976-07-15 ES ES449849A patent/ES449849A1/es not_active Expired
- 1976-07-15 MX MX761774U patent/MX4246E/es unknown
- 1976-07-15 PT PT65374A patent/PT65374B/pt unknown
- 1976-07-16 HU HU70CA00000291A patent/HU172620B/hu unknown
- 1976-07-16 IE IE1583/76A patent/IE43694B1/en unknown
- 1976-07-16 FR FR7621836A patent/FR2318165A1/fr active Granted
1981
- 1981-05-19 CH CH327381A patent/CH630630A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
BG25227A3 (en)	1978-08-10
AU506140B2 (en)	1979-12-13
AU1591376A (en)	1978-01-19
YU40458B (en)	1986-02-28
DD126744A5 (fr)	1977-08-10
LU75384A1 (fr)	1977-07-27
MX4246E (es)	1982-03-02
IE43694L (en)	1977-01-16
NL186008C (nl)	1990-09-03
RO76083A (fr)	1981-06-22
PT65374B (de)	1978-06-08
GR60819B (en)	1978-08-30
FR2318165B1 (fr)	1980-02-01
IE43694B1 (en)	1981-05-06
NL7607871A (nl)	1977-01-18
NL186008B (nl)	1990-04-02
CA1077475A (fr)	1980-05-13
YU175376A (en)	1982-06-30
IL50032A0 (en)	1976-09-30
HU172620B (hu)	1978-11-28
ES449849A1 (es)	1977-08-16
IL50032A (en)	1981-03-31
CH630630A5 (en)	1982-06-30
FR2318165A1 (fr)	1977-02-11
PT65374A (de)	1976-08-01

Legal Events

Date	Code	Title	Description
1996-04-15	SPCF	Supplementary protection certificate filed	Free format text: IKS 44637/830517
1996-06-14	SPCF	Supplementary protection certificate filed	Free format text: IKS 44637/830517, 960117
1996-06-28	SPCG	Supplementary protection certificate granted	Free format text: IKS 44637/830517, 960117, EXPIRES:19980517
1998-06-15	PL	Patent ceased

Publication	Publication Date	Title
DE2265617C3 (de)	1982-05-06	5-Chlor-2- [3-(aminomethyl)-5-methyl-4H-1.2.4-triazol-4-yl]-benzophenone
DE2614406A1 (de)	1976-10-14	Tetracyclische verbindungen, verfahren zu deren herstellung und arzneimittel, enthaltend diese verbindungen
DE3724164A1 (de)	1988-01-28	Neue 1,4-benzodiazepine, ihre herstellung und verwendung
DE2025248A1 (fr)	1970-12-03
CH630912A5 (de)	1982-07-15	Verfahren zur herstellung von 1,2-dihydronaphthalinderivaten.
CH630381A5 (de)	1982-06-15	Verfahren zur herstellung von diazepinderivaten.
DE1670772A1 (de)	1970-07-16	Verfahren zur Herstellung von Benzoxazin-Derivaten
DE2323149A1 (de)	1973-11-22	Thienopyrimidine, verfahren zu deren herstellung und diese verbindungen enthaltende arzneipraeparate
EP0255028A2 (fr)	1988-02-03	1,4-Benzodiazépines, leur préparation et utilisation comme antagonistes PAF
DE3115552A1 (de)	1982-02-18	4,1-benzoxazepine und diese verbindungen enthaltende arzneimittel
DE2533924C3 (de)	1979-05-03	Verfahren zur Herstellung von 6- Aryl-4H-striazolo [3,4-c] thieno [2,3-e] 1,4-diazepinen
CH627181A5 (en)	1981-12-31	Process for the preparation of substituted 6-aryl-4H-s-triazolo[3,4-c]thieno[2,3-e]-1,4-diazepines
CH630902A5 (en)	1982-07-15	Process for preparing novel derivatives of 1,2,3,4,4a,10b-hexahydrobenzo(f)isoquinoline.
DE2346466A1 (de)	1974-04-11	Neue pyrazolopyridobenzodiazepinone mit ihren salzen
EP0084155B1 (fr)	1987-03-25	1,4-Benzodiazépines (1,2) anellés ainsi qu'un procédé pour leur préparation et médicaments contenant ces composés
DE2042758A1 (de)	1971-03-11	Verfahren zur Herstellung von Benzodiazepinderivaten
DE1038047B (de)	1958-09-04	Verfahren zur Herstellung von N-aminoalkylierten Iminodibenzylen und deren Salzen
DE2940737C2 (fr)	1988-12-15
AT330786B (de)	1976-07-26	Verfahren zur herstellung von neuen diazepinderivaten
EP0094668B1 (fr)	1987-07-08	Dérivés de pyrrolo-(3,4-d)(2)benzazépine
DE1954065C3 (de)	1979-09-13	Verfahren zur Herstellung von kondensierten 1,4-Benzodiazepinderivaten
CH633555A5 (de)	1982-12-15	Verfahren zur herstellung von 1-(2-(dialkylamino)aethyl)-6-aryl-4h-s-triazolo(4,3-a)(1,4)benzodiazepinen.
CH642374A5 (de)	1984-04-13	Substituierte 1-piperazinyl-triazolo-thieno-1,4-diazepine.
AT343667B (de)	1978-06-12	Verfahren zur herstellung von neuen piperazinderivaten
AT307426B (de)	1973-05-25	Verfahren zur Herstellung von neuen tricyclischen Benzodiazepinen