DK141726B - Fremgangsmåde til fremstilling af s-triazolo(4,3-a)(1,4)-benzodiazepinderivater. - Google Patents
Fremgangsmåde til fremstilling af s-triazolo(4,3-a)(1,4)-benzodiazepinderivater. Download PDFInfo
- Publication number
- DK141726B DK141726B DK520370A DK520370A DK141726B DK 141726 B DK141726 B DK 141726B DK 520370 A DK520370 A DK 520370A DK 520370 A DK520370 A DK 520370A DK 141726 B DK141726 B DK 141726B
- Authority
- DK
- Denmark
- Prior art keywords
- parts
- benzodiazepine
- phenyl
- chloro
- weight
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- 238000002360 preparation method Methods 0.000 title claims description 7
- LGNWUMGEJQAWQD-UHFFFAOYSA-N 1h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical class N1=CC2=CC=CC=C2N2CN=NC2=C1 LGNWUMGEJQAWQD-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- IEGKHNXXLDCDTE-UHFFFAOYSA-N 1,2-benzodiazepin-2-amine Chemical class NN1C=CC=C2C=CC=CC2=N1 IEGKHNXXLDCDTE-UHFFFAOYSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 239000013078 crystal Substances 0.000 description 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000001953 recrystallisation Methods 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
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- UMBZDAJGYNJMGS-UHFFFAOYSA-N 7-chloro-5-phenyl-3h-1,4-benzodiazepin-2-amine Chemical compound N=1CC(N)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 UMBZDAJGYNJMGS-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 5
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- KQQZXSHUXDNCNR-UHFFFAOYSA-N n'-(7-chloro-5-phenyl-3h-1,4-benzodiazepin-2-yl)benzohydrazide Chemical compound C12=CC(Cl)=CC=C2N=C(NNC(=O)C=2C=CC=CC=2)CN=C1C1=CC=CC=C1 KQQZXSHUXDNCNR-UHFFFAOYSA-N 0.000 description 3
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- HPQLMQCOAKIPLL-UHFFFAOYSA-N n-[(7-chloro-5-phenyl-3h-1,4-benzodiazepin-2-yl)amino]formamide Chemical compound C12=CC(Cl)=CC=C2N=C(NNC=O)CN=C1C1=CC=CC=C1 HPQLMQCOAKIPLL-UHFFFAOYSA-N 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- DWPZNZAUIXWVRE-UHFFFAOYSA-N 1-benzyl-8-chloro-6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C=1C(Cl)=CC=C(N23)C=1C(C=1C=CC=CC=1)=NCC3=NN=C2CC1=CC=CC=C1 DWPZNZAUIXWVRE-UHFFFAOYSA-N 0.000 description 1
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- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/20—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8487069A JPS4927880B1 (enrdf_load_stackoverflow) | 1969-10-23 | 1969-10-23 | |
| JP8487069 | 1969-10-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DK141726B true DK141726B (da) | 1980-06-02 |
| DK141726C DK141726C (enrdf_load_stackoverflow) | 1980-10-27 |
Family
ID=13842822
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK520370A DK141726B (da) | 1969-10-23 | 1970-10-14 | Fremgangsmåde til fremstilling af s-triazolo(4,3-a)(1,4)-benzodiazepinderivater. |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4927880B1 (enrdf_load_stackoverflow) |
| AT (1) | AT299958B (enrdf_load_stackoverflow) |
| CH (1) | CH550810A (enrdf_load_stackoverflow) |
| DK (1) | DK141726B (enrdf_load_stackoverflow) |
| ES (2) | ES384814A1 (enrdf_load_stackoverflow) |
| FI (1) | FI51699C (enrdf_load_stackoverflow) |
| NL (1) | NL7015430A (enrdf_load_stackoverflow) |
| SE (1) | SE383348B (enrdf_load_stackoverflow) |
| YU (1) | YU34881B (enrdf_load_stackoverflow) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3879406A (en) * | 1972-07-13 | 1975-04-22 | Hoffmann La Roche | Preparation of triazolobenzodiazepines |
| US4155913A (en) * | 1973-02-08 | 1979-05-22 | Hoffmann-La Roche Inc. | Thienotriazolodiazepine derivatives |
-
1969
- 1969-10-23 JP JP8487069A patent/JPS4927880B1/ja active Pending
-
1970
- 1970-10-14 DK DK520370A patent/DK141726B/da not_active IP Right Cessation
- 1970-10-21 NL NL7015430A patent/NL7015430A/xx unknown
- 1970-10-21 YU YU257470A patent/YU34881B/xx unknown
- 1970-10-22 FI FI285070A patent/FI51699C/fi active
- 1970-10-22 ES ES384814A patent/ES384814A1/es not_active Expired
- 1970-10-22 SE SE1428570A patent/SE383348B/xx unknown
- 1970-10-23 CH CH1571270A patent/CH550810A/de not_active IP Right Cessation
- 1970-10-23 AT AT957570A patent/AT299958B/de not_active IP Right Cessation
-
1973
- 1973-03-31 ES ES413244A patent/ES413244A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT299958B (de) | 1972-07-10 |
| NL7015430A (enrdf_load_stackoverflow) | 1971-04-27 |
| JPS4927880B1 (enrdf_load_stackoverflow) | 1974-07-22 |
| SE383348B (sv) | 1976-03-08 |
| FI51699C (fi) | 1977-03-10 |
| FI51699B (enrdf_load_stackoverflow) | 1976-11-30 |
| CH550810A (de) | 1974-06-28 |
| YU257470A (en) | 1979-10-31 |
| ES413244A1 (es) | 1976-01-01 |
| DK141726C (enrdf_load_stackoverflow) | 1980-10-27 |
| ES384814A1 (es) | 1973-09-01 |
| YU34881B (en) | 1980-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUP | Patent expired |