GB1299151A - 7-phenylpyrimido-benzodiazepine derivatives - Google Patents
7-phenylpyrimido-benzodiazepine derivativesInfo
- Publication number
- GB1299151A GB1299151A GB07986/71A GB1798671A GB1299151A GB 1299151 A GB1299151 A GB 1299151A GB 07986/71 A GB07986/71 A GB 07986/71A GB 1798671 A GB1798671 A GB 1798671A GB 1299151 A GB1299151 A GB 1299151A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloro
- alkyl
- reaction
- reacting
- hydrogen
- 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 238000006243 chemical reaction Methods 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- -1 sulphonamido Chemical group 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- 229910021529 ammonia Inorganic materials 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- 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 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 2
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 abstract 2
- UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 abstract 1
- 150000004911 1,4-diazepines Chemical class 0.000 abstract 1
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 abstract 1
- UXMVQZIDRMBYRK-UHFFFAOYSA-N 6-chloro-2-methyl-3,1-benzoxazin-4-one Chemical compound C1=C(Cl)C=C2C(=O)OC(C)=NC2=C1 UXMVQZIDRMBYRK-UHFFFAOYSA-N 0.000 abstract 1
- YDJDZKBEEQKDMA-UHFFFAOYSA-N 7-phenyl-1H-pyrimido[4,5-i][1,2]benzodiazepine Chemical class C1(=CC=CC=C1)C=1C2=C(C3=C(C=CC=NN3)C1)C=NC=N2 YDJDZKBEEQKDMA-UHFFFAOYSA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229960001413 acetanilide Drugs 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000002921 anti-spasmodic effect Effects 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 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 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 abstract 1
- 239000003158 myorelaxant agent Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 229960000380 propiolactone Drugs 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4760270A | 1970-06-18 | 1970-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1299151A true GB1299151A (en) | 1972-12-06 |
Family
ID=21949903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB07986/71A Expired GB1299151A (en) | 1970-06-18 | 1971-05-28 | 7-phenylpyrimido-benzodiazepine derivatives |
Country Status (17)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE790356A (fr) * | 1971-10-21 | 1973-04-20 | Takeda Chemical Industries Ltd | Derives de benzodiazepine |
| BE790839A (fr) * | 1971-11-02 | 1973-04-30 | Upjohn Co | Nouvelles benzodiazepines, leur procede de preparation et medicament les contenant |
| BE793118A (fr) * | 1971-12-24 | 1973-06-21 | Takeda Chemical Industries Ltd | Derives de benzodiazocine |
| US3842080A (en) * | 1973-01-15 | 1974-10-15 | Upjohn Co | 7-phenylpyrimido(1,2-a)(1,4)benzodiazepin-1(5h)-ones |
| GB1402810A (en) * | 1973-01-15 | 1975-08-13 | Upjohn Co | Pyrimidobenzodiazepines |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1545214A (fr) * | 1966-11-23 | 1968-11-08 | Hoffmann La Roche | Procédé pour la préparation de dérivés de benzodiazépine |
| BE755139A (fr) * | 1969-08-21 | 1971-02-22 | Upjohn Co | Derives de benzodiazepinones, leurs intermediaires, et leur preparatio |
| BE759099A (fr) * | 1969-11-18 | 1971-04-30 | Takeda Chemical Industries Ltd | Procede de fabrication de composes heterocycliques |
-
1971
- 1971-05-25 ZA ZA713364A patent/ZA713364B/xx unknown
- 1971-05-28 IL IL36948A patent/IL36948A/en unknown
- 1971-05-28 GB GB07986/71A patent/GB1299151A/en not_active Expired
- 1971-06-04 DE DE2127812A patent/DE2127812C2/de not_active Expired
- 1971-06-07 CH CH1638474A patent/CH569017A5/xx not_active IP Right Cessation
- 1971-06-07 CH CH830171A patent/CH560217A5/xx not_active IP Right Cessation
- 1971-06-10 PH PH12532A patent/PH9777A/en unknown
- 1971-06-11 YU YU01514/71A patent/YU151471A/xx unknown
- 1971-06-16 HU HUUO70A patent/HU163364B/hu unknown
- 1971-06-16 SE SE7107817A patent/SE370238B/xx unknown
- 1971-06-17 FR FR7122104A patent/FR2100782B1/fr not_active Expired
- 1971-06-17 NL NL7108319.A patent/NL167433C/xx not_active IP Right Cessation
- 1971-06-17 ES ES392364A patent/ES392364A1/es not_active Expired
- 1971-06-17 OA OA54273A patent/OA03874A/xx unknown
- 1971-06-18 SU SU1677616A patent/SU406358A3/ru active
- 1971-06-18 BE BE768702A patent/BE768702A/xx not_active IP Right Cessation
- 1971-06-18 JP JP4338871A patent/JPS5425040B1/ja active Pending
-
1972
- 1972-04-28 AR AR241713A patent/AR201546A1/es active
- 1972-04-28 AR AR241712A patent/AR199278A1/es active
- 1972-04-28 AR AR241710A patent/AR198784A1/es active
- 1972-04-28 AR AR241711A patent/AR200111A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| AR198784A1 (es) | 1974-07-24 |
| CH569017A5 (enrdf_load_stackoverflow) | 1975-11-14 |
| BE768702A (fr) | 1971-12-20 |
| DE2127812C2 (de) | 1982-12-02 |
| AR201546A1 (es) | 1975-03-31 |
| SU406358A3 (enrdf_load_stackoverflow) | 1973-11-05 |
| NL167433C (nl) | 1981-12-16 |
| PH9777A (en) | 1976-03-17 |
| NL167433B (nl) | 1981-07-16 |
| ZA713364B (en) | 1972-01-26 |
| IL36948A0 (en) | 1971-07-28 |
| IL36948A (en) | 1974-11-29 |
| SE370238B (enrdf_load_stackoverflow) | 1974-10-07 |
| AR199278A1 (es) | 1974-08-23 |
| JPS5425040B1 (enrdf_load_stackoverflow) | 1979-08-24 |
| FR2100782B1 (enrdf_load_stackoverflow) | 1975-01-17 |
| AR200111A1 (es) | 1974-10-24 |
| ES392364A1 (es) | 1973-10-01 |
| DE2127812A1 (de) | 1971-12-23 |
| OA03874A (fr) | 1971-12-24 |
| FR2100782A1 (enrdf_load_stackoverflow) | 1972-03-24 |
| CH560217A5 (enrdf_load_stackoverflow) | 1975-03-27 |
| NL7108319A (enrdf_load_stackoverflow) | 1971-12-21 |
| HU163364B (enrdf_load_stackoverflow) | 1973-07-28 |
| YU151471A (en) | 1979-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |