CA1058173A - Process for production of 8-bromothienotriazolo-1,4-diazepines - Google Patents
Process for production of 8-bromothienotriazolo-1,4-diazepinesInfo
- Publication number
- CA1058173A CA1058173A CA244,192A CA244192A CA1058173A CA 1058173 A CA1058173 A CA 1058173A CA 244192 A CA244192 A CA 244192A CA 1058173 A CA1058173 A CA 1058173A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- thieno
- triazolo
- diazepine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 27
- 230000008569 process Effects 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 42
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 11
- 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 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 10
- -1 thallium cation Chemical class 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052709 silver Inorganic materials 0.000 claims description 5
- 239000004332 silver Substances 0.000 claims description 5
- 229910052716 thallium Inorganic materials 0.000 claims description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910001961 silver nitrate Inorganic materials 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 150000005171 halobenzenes Chemical class 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 6
- FOIXSVOLVBLSDH-UHFFFAOYSA-N Silver ion Chemical group [Ag+] FOIXSVOLVBLSDH-UHFFFAOYSA-N 0.000 claims 2
- UMSGKTJDUHERQW-UHFFFAOYSA-N Brotizolam Chemical compound C1=2C=C(Br)SC=2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Cl UMSGKTJDUHERQW-UHFFFAOYSA-N 0.000 claims 1
- SCPDYXVPFQQFES-UHFFFAOYSA-N ClC1=CC=CC=C1C(C(N1C2)=NN2Br)=NCC2=C1[S+](C1CCCCC1)C=C2 Chemical compound ClC1=CC=CC=C1C(C(N1C2)=NN2Br)=NCC2=C1[S+](C1CCCCC1)C=C2 SCPDYXVPFQQFES-UHFFFAOYSA-N 0.000 claims 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical group [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- 229940054334 silver cation Drugs 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000003204 tranquilizing agent Substances 0.000 abstract description 2
- 230000002936 tranquilizing effect Effects 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 150000003475 thallium Chemical class 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
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000004911 1,4-diazepines Chemical class 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000002560 therapeutic procedure 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
- C07D495/12—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)
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 |
|---|---|
| CA1058173A true CA1058173A (en) | 1979-07-10 |
Family
ID=5937404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA244,192A Expired CA1058173A (en) | 1975-01-27 | 1976-01-26 | Process for production of 8-bromothienotriazolo-1,4-diazepines |
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) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2701752A1 (de) * | 1977-01-18 | 1978-07-20 | Boehringer Sohn Ingelheim | 8-jod-l-methyl-6-o-chlorphenyl-4h-s -triazolo eckige klammer auf 3,4c eckige klammer zu thieno eckige klammer auf 2,3e eckige klammer zu l,4-diazepin, verfahren zu seiner herstellung und seine verwendung in pharmazeutischen praeparaten |
| 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 |
| DE3502392A1 (de) * | 1985-01-25 | 1986-07-31 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue thieno-triazolo-1,4-diazepino-2- carbonsaeureamide, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen |
| DE3624779C2 (de) * | 1986-07-22 | 1996-03-07 | Boehringer Ingelheim Kg | Verfahren zur Herstellung von Thieno-triazolo-1,4-diazepino-2- carbonsäureamiden |
| EP0387613A1 (de) * | 1989-03-03 | 1990-09-19 | Boehringer Ingelheim Kg | Neue Thienodiazepine |
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| DE2503235A1 (de) | 1976-07-29 |
| ES444612A1 (es) | 1977-05-01 |
| SE7600847L (sv) | 1976-07-28 |
| FI753638A7 (enrdf_load_stackoverflow) | 1976-07-28 |
| 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 |
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