DE2503235A1 - Neues verfahren zur herstellung von 8-brom-thieno-triazolo-1,4-diazepinen - Google Patents
Neues verfahren zur herstellung von 8-brom-thieno-triazolo-1,4-diazepinenInfo
- Publication number
- DE2503235A1 DE2503235A1 DE19752503235 DE2503235A DE2503235A1 DE 2503235 A1 DE2503235 A1 DE 2503235A1 DE 19752503235 DE19752503235 DE 19752503235 DE 2503235 A DE2503235 A DE 2503235A DE 2503235 A1 DE2503235 A1 DE 2503235A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- compounds
- bromine
- silver
- meanings
- 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.)
- Withdrawn
Links
- 229910052794 bromium Inorganic materials 0.000 title claims abstract description 8
- 229910052709 silver Inorganic materials 0.000 title claims abstract description 6
- 239000004332 silver Substances 0.000 title claims abstract description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 title claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 title claims description 6
- 150000003475 thallium Chemical class 0.000 title description 2
- 125000001246 bromo group Chemical group Br* 0.000 title 1
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 229910052716 thallium Inorganic materials 0.000 claims abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 20
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- -1 thallium cation Chemical class 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- BBBFJLBPOGFECG-VJVYQDLKSA-N calcitonin Chemical group N([C@H](C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H]([C@@H](C)O)C(=O)N1[C@@H](CCC1)C(N)=O)C(C)C)C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1 BBBFJLBPOGFECG-VJVYQDLKSA-N 0.000 claims 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003204 tranquilizing agent Substances 0.000 abstract description 2
- 230000002936 tranquilizing effect Effects 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 229910001961 silver nitrate Inorganic materials 0.000 description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- ZJRCIQAMTAINCB-UHFFFAOYSA-N benzoylacetonitrile Chemical class N#CCC(=O)C1=CC=CC=C1 ZJRCIQAMTAINCB-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 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
- C07D495/12—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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752503235 DE2503235A1 (de) | 1975-01-27 | 1975-01-27 | Neues verfahren zur herstellung von 8-brom-thieno-triazolo-1,4-diazepinen |
| LU74028A LU74028A1 (enrdf_load_stackoverflow) | 1975-01-27 | 1975-12-16 | |
| FI753638A FI753638A7 (enrdf_load_stackoverflow) | 1975-01-27 | 1975-12-23 | |
| ES444612A ES444612A1 (es) | 1975-01-27 | 1976-01-26 | Procedimiento para la preparacion de 8-bromo-tieno-triazol- 1,4-diazepinas. |
| NO760240A NO760240L (enrdf_load_stackoverflow) | 1975-01-27 | 1976-01-26 | |
| CA244,192A CA1058173A (en) | 1975-01-27 | 1976-01-26 | Process for production of 8-bromothienotriazolo-1,4-diazepines |
| DK29276*#A DK29276A (da) | 1975-01-27 | 1976-01-26 | Fremgangsmade til fremstilling af 8-bromothieno-triazolo-1,4-diazepiner |
| JP51007401A JPS51100096A (enrdf_load_stackoverflow) | 1975-01-27 | 1976-01-26 | |
| SE7600847A SE7600847L (sv) | 1975-01-27 | 1976-01-27 | Nytt forfarande for framstellning av 8-bromtienotriazolo-1,4-diazepiner |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752503235 DE2503235A1 (de) | 1975-01-27 | 1975-01-27 | Neues verfahren zur herstellung von 8-brom-thieno-triazolo-1,4-diazepinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2503235A1 true DE2503235A1 (de) | 1976-07-29 |
Family
ID=5937404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752503235 Withdrawn DE2503235A1 (de) | 1975-01-27 | 1975-01-27 | Neues verfahren zur herstellung von 8-brom-thieno-triazolo-1,4-diazepinen |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS51100096A (enrdf_load_stackoverflow) |
| CA (1) | CA1058173A (enrdf_load_stackoverflow) |
| DE (1) | DE2503235A1 (enrdf_load_stackoverflow) |
| DK (1) | DK29276A (enrdf_load_stackoverflow) |
| ES (1) | ES444612A1 (enrdf_load_stackoverflow) |
| FI (1) | FI753638A7 (enrdf_load_stackoverflow) |
| LU (1) | LU74028A1 (enrdf_load_stackoverflow) |
| NO (1) | NO760240L (enrdf_load_stackoverflow) |
| SE (1) | SE7600847L (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2377407A1 (fr) * | 1977-01-18 | 1978-08-11 | Boehringer Sohn Ingelheim | 8-iodo-1-methyl-6-o-chlorophenyl-4h-s-triazolo (3,4c) thieno (2,3e), 1,4-diazepine, procedes pour sa preparation et son utilisation dans des preparations pharmaceutiques |
| DE3624779A1 (de) * | 1986-07-22 | 1988-01-28 | Boehringer Ingelheim Kg | Verfahren zur herstellung von thieno-triazolo-1,4-diazepino-2- carbonsaeureamiden |
| EP0387613A1 (de) * | 1989-03-03 | 1990-09-19 | Boehringer Ingelheim Kg | Neue Thienodiazepine |
| US4968794A (en) * | 1985-01-25 | 1990-11-06 | Boehringer Ingelheim Kg | Thieno-traizolo-1,4-diazepino-2-carboxylic acid amides |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI63033C (fi) * | 1977-07-21 | 1983-04-11 | Boehringer Sohn Ingelheim | Foerfarande foer framstaellning av anxiolytiska tranquilliserande sedativa och/eller neuroleptiska substituerade 1-piperazinyl-4h-s-triazolo(3,4-c)tieno(2,3-e)-1,4-diazepiner |
-
1975
- 1975-01-27 DE DE19752503235 patent/DE2503235A1/de not_active Withdrawn
- 1975-12-16 LU LU74028A patent/LU74028A1/xx unknown
- 1975-12-23 FI FI753638A patent/FI753638A7/fi not_active Application Discontinuation
-
1976
- 1976-01-26 JP JP51007401A patent/JPS51100096A/ja active Pending
- 1976-01-26 NO NO760240A patent/NO760240L/no unknown
- 1976-01-26 ES ES444612A patent/ES444612A1/es not_active Expired
- 1976-01-26 CA CA244,192A patent/CA1058173A/en not_active Expired
- 1976-01-26 DK DK29276*#A patent/DK29276A/da unknown
- 1976-01-27 SE SE7600847A patent/SE7600847L/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2377407A1 (fr) * | 1977-01-18 | 1978-08-11 | Boehringer Sohn Ingelheim | 8-iodo-1-methyl-6-o-chlorophenyl-4h-s-triazolo (3,4c) thieno (2,3e), 1,4-diazepine, procedes pour sa preparation et son utilisation dans des preparations pharmaceutiques |
| US4968794A (en) * | 1985-01-25 | 1990-11-06 | Boehringer Ingelheim Kg | Thieno-traizolo-1,4-diazepino-2-carboxylic acid amides |
| US5082839A (en) * | 1985-01-25 | 1992-01-21 | Boehringer Ingelheim Gmbh | Thieno-triazolo-1,4-diazepino-2-carboxylic acid amides |
| DE3624779A1 (de) * | 1986-07-22 | 1988-01-28 | Boehringer Ingelheim Kg | Verfahren zur herstellung von thieno-triazolo-1,4-diazepino-2- carbonsaeureamiden |
| EP0387613A1 (de) * | 1989-03-03 | 1990-09-19 | Boehringer Ingelheim Kg | Neue Thienodiazepine |
Also Published As
| Publication number | Publication date |
|---|---|
| ES444612A1 (es) | 1977-05-01 |
| SE7600847L (sv) | 1976-07-28 |
| FI753638A7 (enrdf_load_stackoverflow) | 1976-07-28 |
| CA1058173A (en) | 1979-07-10 |
| DK29276A (da) | 1976-07-28 |
| JPS51100096A (enrdf_load_stackoverflow) | 1976-09-03 |
| LU74028A1 (enrdf_load_stackoverflow) | 1977-02-15 |
| NO760240L (enrdf_load_stackoverflow) | 1976-07-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3918979A1 (de) | Verfahren zur herstellung von pyrazol und dessen derivaten | |
| EP0040356B1 (de) | Verfahren zur Herstellung von Trimethylsilylcyanid | |
| DE1620694B2 (de) | Verfahren zur Herstellung von 5-Methyl-7-diäthylamino-s-triazolo [1,5-a] pyrimidin und seinen Salzen mit Säuren | |
| DE2147023A1 (de) | Verfahren zur herstellung von 1htetrazol-verbindungen | |
| DE2503235A1 (de) | Neues verfahren zur herstellung von 8-brom-thieno-triazolo-1,4-diazepinen | |
| DE2741386C3 (de) | Verfahren zur Isomerisierung von cis,cis- und cis, trans-Isomeren des Di-(p-aminocyclohexyl)-methans und dabei als Zwischenprodukte gebildete Bis-benzaldimine | |
| DE2635624A1 (de) | Verfahren zur herstellung von hydrazinen | |
| DE2533924B2 (de) | Verfahren zur Herstellung von 6- Aryl-4H-striazolo [3,4-c] thieno [23-e] 1,4-diazepinen | |
| DE2503736A1 (de) | Verfahren zur herstellung von 2-oxo- 1,2-dihydro-chinazolinen | |
| DE2642608A1 (de) | 4-hydroxymethyl-2-pyrrolidinone und verfahren zu ihrer herstellung | |
| DE2601399C2 (de) | Cis-β-[Trimethylammonium]-acrylnitriltosylat, Verfahren zu dessen Herstellung und dessen Verwendung zur Herstellung von Cyclocytidintosylat | |
| DE3434553C2 (enrdf_load_stackoverflow) | ||
| DE3150918C1 (de) | Verfahren zur Herstellung von Aniliden in der Ergolinreihe | |
| DE1695199A1 (de) | Verfahren zur Herstellung von Isoxazol-Verbindungen | |
| EP0173153B1 (de) | Neue benzokondensierte, fluorierte, heterocyclische Verbindungen, ein Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE2534811A1 (de) | Verfahren zur herstellung von cephalosporinen | |
| DE969813C (de) | Verfahren zur Herstellung von Aminsulfenhalogeniden | |
| AT334379B (de) | Verfahren zur herstellung von neuen 6-aza-3h-1,4-benzodiazepinen und deren salzen | |
| DE2521895A1 (de) | Alpha-amino-2-adamantylessigsaeure und verfahren zu ihrer herstellung | |
| DE2428180A1 (de) | Verfahren zur herstellung von substituierten chlorbenzolderivaten aus benzolsulfochloriden | |
| DE1445659C (de) | Pyndylphosphorverbindungen und Verfahren zu ihrer Herstellung | |
| DE2944953C2 (de) | Verfahren zur Herstellung von N,N'-1,1-Dimethyltrimethylen-bis-benzamid | |
| DE1768531C3 (de) | Verfahren zur Herstellung fluorierter organischer Verbindungen | |
| EP1046632A1 (de) | Verfahren zur Herstellung von 1-substituierten 2,4-Dinitrobenzolen | |
| DE965490C (de) | Verfahren zur Herstellung von aromatischen Sulfoniumverbindungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |