CH570384A5 - 1-acyl-5-phenyl-1h-1,5-benzodiazepine-2,4-(3h,5h)-diones - - from substd 2-aminodiphenyl amines via n-phenyl-n-(2-acylaminopheny - Google Patents
1-acyl-5-phenyl-1h-1,5-benzodiazepine-2,4-(3h,5h)-diones - - from substd 2-aminodiphenyl amines via n-phenyl-n-(2-acylaminophenyInfo
- Publication number
- CH570384A5 CH570384A5 CH1160975A CH1160975A CH570384A5 CH 570384 A5 CH570384 A5 CH 570384A5 CH 1160975 A CH1160975 A CH 1160975A CH 1160975 A CH1160975 A CH 1160975A CH 570384 A5 CH570384 A5 CH 570384A5
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- benzodiazepine
- ethyl ester
- chloro
- malonic acid
- Prior art date
Links
- -1 2-aminodiphenyl amines Chemical class 0.000 title claims abstract description 61
- 150000001266 acyl halides Chemical class 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 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
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 4
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 229910006124 SOCl2 Inorganic materials 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
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000005504 styryl group Chemical group 0.000 abstract 1
- 239000003204 tranquilizing agent Substances 0.000 abstract 1
- 238000002844 melting Methods 0.000 description 35
- 230000008018 melting Effects 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 238000006798 ring closing metathesis reaction Methods 0.000 description 22
- NBKNFNAHFNVUOW-UHFFFAOYSA-N 3-ethoxy-3-oxopropanoic acid;hydrochloride Chemical compound Cl.CCOC(=O)CC(O)=O NBKNFNAHFNVUOW-UHFFFAOYSA-N 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000007127 saponification reaction Methods 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 2
- XGTITDAWBWGDIQ-UHFFFAOYSA-N 7-chloro-2,4-dioxo-5-phenyl-1,5-benzodiazepine-1-carbaldehyde Chemical compound C12=CC(Cl)=CC=C2N(C=O)C(=O)CC(=O)N1C1=CC=CC=C1 XGTITDAWBWGDIQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- CGJMROBVSBIBKP-UHFFFAOYSA-N malonamic acid Chemical compound NC(=O)CC(O)=O CGJMROBVSBIBKP-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-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
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT174471A AT308755B (de) | 1971-03-01 | 1971-03-01 | Verfahren zur Herstellung von 1-Acyl-5-phenyl-1H-1,5-benzodiazepin-2,4-(3H,5H)-dionen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH570384A5 true CH570384A5 (en) | 1975-12-15 |
Family
ID=3520071
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1160975A CH570384A5 (en) | 1971-03-01 | 1972-02-29 | 1-acyl-5-phenyl-1h-1,5-benzodiazepine-2,4-(3h,5h)-diones - - from substd 2-aminodiphenyl amines via n-phenyl-n-(2-acylaminopheny |
| CH290072A CH570987A5 (cg-RX-API-DMAC10.html) | 1971-03-01 | 1972-02-29 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH290072A CH570987A5 (cg-RX-API-DMAC10.html) | 1971-03-01 | 1972-02-29 |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT308755B (cg-RX-API-DMAC10.html) |
| CA (1) | CA992540A (cg-RX-API-DMAC10.html) |
| CH (2) | CH570384A5 (cg-RX-API-DMAC10.html) |
| DK (1) | DK137725B (cg-RX-API-DMAC10.html) |
| ES (2) | ES400238A1 (cg-RX-API-DMAC10.html) |
| NL (1) | NL7202671A (cg-RX-API-DMAC10.html) |
| SE (3) | SE389339B (cg-RX-API-DMAC10.html) |
-
1971
- 1971-03-01 AT AT174471A patent/AT308755B/de not_active IP Right Cessation
-
1972
- 1972-02-28 ES ES400238A patent/ES400238A1/es not_active Expired
- 1972-02-29 SE SE7202557A patent/SE389339B/xx unknown
- 1972-02-29 CA CA135,795A patent/CA992540A/en not_active Expired
- 1972-02-29 CH CH1160975A patent/CH570384A5/de not_active IP Right Cessation
- 1972-02-29 SE SE7407780A patent/SE393803B/xx unknown
- 1972-02-29 DK DK92372AA patent/DK137725B/da unknown
- 1972-02-29 CH CH290072A patent/CH570987A5/xx not_active IP Right Cessation
- 1972-03-01 NL NL7202671A patent/NL7202671A/xx not_active Application Discontinuation
-
1974
- 1974-04-09 ES ES425165A patent/ES425165A1/es not_active Expired
- 1974-06-12 SE SE7407780A patent/SE7407780L/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE7407780L (cg-RX-API-DMAC10.html) | 1974-06-12 |
| SE393803B (sv) | 1977-05-23 |
| SE389339B (sv) | 1976-11-01 |
| AT308755B (de) | 1973-07-25 |
| DK137725C (cg-RX-API-DMAC10.html) | 1978-10-02 |
| NL7202671A (cg-RX-API-DMAC10.html) | 1972-09-05 |
| ES400238A1 (es) | 1975-06-16 |
| CA992540A (en) | 1976-07-06 |
| CH570987A5 (cg-RX-API-DMAC10.html) | 1975-12-31 |
| ES425165A1 (es) | 1976-07-01 |
| DK137725B (da) | 1978-04-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |