DE2114844A1 - Neues Verfahren zur Herstellung von l-Acyl-S-phenyl-lH-l^-benzodiazepin^^-(3H,5H)-dionen - Google Patents
Neues Verfahren zur Herstellung von l-Acyl-S-phenyl-lH-l^-benzodiazepin^^-(3H,5H)-dionenInfo
- Publication number
- DE2114844A1 DE2114844A1 DE19712114844 DE2114844A DE2114844A1 DE 2114844 A1 DE2114844 A1 DE 2114844A1 DE 19712114844 DE19712114844 DE 19712114844 DE 2114844 A DE2114844 A DE 2114844A DE 2114844 A1 DE2114844 A1 DE 2114844A1
- Authority
- DE
- Germany
- Prior art keywords
- phenyl
- benzodiazepine
- radical
- acyl
- dione
- 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.)
- Pending
Links
- 229940125681 anticonvulsant agent Drugs 0.000 title 1
- 239000001961 anticonvulsive agent Substances 0.000 title 1
- 229940035363 muscle relaxants Drugs 0.000 title 1
- 239000003158 myorelaxant agent Substances 0.000 title 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- -1 alkyl radical Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 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
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000004970 halomethyl group Chemical group 0.000 abstract 1
- 125000005504 styryl group Chemical group 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001266 acyl halides Chemical class 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZBFPPOKYYPQMBZ-UHFFFAOYSA-N 1-acetyl-7-chloro-5-phenyl-1,5-benzodiazepine-2,4-dione Chemical compound O=C1CC(=O)N(C(=O)C)C2=CC=C(Cl)C=C2N1C1=CC=CC=C1 ZBFPPOKYYPQMBZ-UHFFFAOYSA-N 0.000 description 1
- GQFDPYJUUFYOFM-UHFFFAOYSA-N 1-benzoyl-7-bromo-5-phenyl-1,5-benzodiazepine-2,4-dione Chemical compound O=C1CC(=O)N(C=2C=CC=CC=2)C2=CC(Br)=CC=C2N1C(=O)C1=CC=CC=C1 GQFDPYJUUFYOFM-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- FVNSAGQEFPPDKP-UHFFFAOYSA-N 7-chloro-5-phenyl-1-propanoyl-1,5-benzodiazepine-2,4-dione Chemical compound O=C1CC(=O)N(C(=O)CC)C2=CC=C(Cl)C=C2N1C1=CC=CC=C1 FVNSAGQEFPPDKP-UHFFFAOYSA-N 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000008164 mustard oil Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 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
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07D243/12—1,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712114844 DE2114844A1 (de) | 1971-03-26 | 1971-03-26 | Neues Verfahren zur Herstellung von l-Acyl-S-phenyl-lH-l^-benzodiazepin^^-(3H,5H)-dionen |
| CH432972A CH566325A5 (enExample) | 1971-03-26 | 1972-03-23 | |
| CA138,024A CA959836A (en) | 1971-03-26 | 1972-03-24 | Process for the production of 1-acyl-5-phenyl 1h-1,5-benzodiazepine-2,4-(3h,5h)-diones |
| NL7204008A NL7204008A (enExample) | 1971-03-26 | 1972-03-24 | |
| AT258472A AT315850B (de) | 1971-03-26 | 1972-03-24 | Verfahren zur Herstellung von 1-Acyl-5-phenyl-1H-1,5-benzodiazepin-2,4-(3H,5H)-dionen |
| ES401130A ES401130A1 (es) | 1971-03-26 | 1972-03-24 | Nuevo procedimiento de preparacion de 1-acil-5-fenil-1h-1,5- benzodiazepin-2, 4-(3h, 5h)-dionas. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712114844 DE2114844A1 (de) | 1971-03-26 | 1971-03-26 | Neues Verfahren zur Herstellung von l-Acyl-S-phenyl-lH-l^-benzodiazepin^^-(3H,5H)-dionen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2114844A1 true DE2114844A1 (de) | 1972-10-12 |
Family
ID=5802915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712114844 Pending DE2114844A1 (de) | 1971-03-26 | 1971-03-26 | Neues Verfahren zur Herstellung von l-Acyl-S-phenyl-lH-l^-benzodiazepin^^-(3H,5H)-dionen |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT315850B (enExample) |
| CA (1) | CA959836A (enExample) |
| CH (1) | CH566325A5 (enExample) |
| DE (1) | DE2114844A1 (enExample) |
| ES (1) | ES401130A1 (enExample) |
| NL (1) | NL7204008A (enExample) |
-
1971
- 1971-03-26 DE DE19712114844 patent/DE2114844A1/de active Pending
-
1972
- 1972-03-23 CH CH432972A patent/CH566325A5/xx not_active IP Right Cessation
- 1972-03-24 NL NL7204008A patent/NL7204008A/xx not_active Application Discontinuation
- 1972-03-24 CA CA138,024A patent/CA959836A/en not_active Expired
- 1972-03-24 AT AT258472A patent/AT315850B/de not_active IP Right Cessation
- 1972-03-24 ES ES401130A patent/ES401130A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES401130A1 (es) | 1975-02-16 |
| NL7204008A (enExample) | 1972-09-28 |
| CH566325A5 (enExample) | 1975-09-15 |
| CA959836A (en) | 1974-12-24 |
| AT315850B (de) | 1974-06-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |