CH549585A - 1 4-benzodiazepine derivatives - Google Patents
1 4-benzodiazepine derivativesInfo
- Publication number
- CH549585A CH549585A CH54167A CH54167A CH549585A CH 549585 A CH549585 A CH 549585A CH 54167 A CH54167 A CH 54167A CH 54167 A CH54167 A CH 54167A CH 549585 A CH549585 A CH 549585A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- alkyl
- hydrogen
- compound
- compounds
- Prior art date
Links
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 11
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 150000004965 peroxy acids Chemical class 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- -1 carbobenzoxyamino Chemical group 0.000 claims 1
- 229910000039 hydrogen halide Inorganic materials 0.000 claims 1
- 239000012433 hydrogen halide Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000005544 phthalimido group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- 150000001448 anilines Chemical class 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 231100000331 toxic Toxicity 0.000 abstract 1
- 230000002588 toxic effect Effects 0.000 abstract 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 239000012965 benzophenone Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000012902 Nervous system disease Diseases 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- WYCLKVQLVUQKNZ-UHFFFAOYSA-N Halazepam Chemical compound N=1CC(=O)N(CC(F)(F)F)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 WYCLKVQLVUQKNZ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QPKPRNRVRFRJLL-UHFFFAOYSA-N [3-amino-5-chloro-2-(2,2,2-trifluoroethyl)phenyl]-phenylmethanone Chemical compound NC1=CC(Cl)=CC(C(=O)C=2C=CC=CC=2)=C1CC(F)(F)F QPKPRNRVRFRJLL-UHFFFAOYSA-N 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 230000001914 calming effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 229940125723 sedative agent Drugs 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 1
- RKOUFQLNMRAACI-UHFFFAOYSA-N 1,1,1-trifluoro-2-iodoethane Chemical compound FC(F)(F)CI RKOUFQLNMRAACI-UHFFFAOYSA-N 0.000 description 1
- PJIXKADJKGDJIR-UHFFFAOYSA-N 7-chloro-4-oxido-5-phenyl-1-(2,2,2-trifluoroethyl)-3h-1,4-benzodiazepin-4-ium-2-one Chemical compound C12=CC(Cl)=CC=C2N(CC(F)(F)F)C(=O)C[N+]([O-])=C1C1=CC=CC=C1 PJIXKADJKGDJIR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241000272517 Anseriformes Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 229940035363 muscle relaxants Drugs 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- WZTIKNRSYKDRQF-UHFFFAOYSA-N n-(2-benzoyl-4-chlorophenyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WZTIKNRSYKDRQF-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1836769A CH509332A (de) | 1966-01-14 | 1967-01-11 | Verfahren zur Herstellung von neuen 1,4-Benzodiazepinen |
| CH1836569A CH485743A (de) | 1966-01-14 | 1967-01-11 | Verfahren zur Herstellung von neuen 1,4-Benzodiazepinen und ihren 4-Oxyden |
| CH1836669A CH505842A (de) | 1966-01-14 | 1967-01-11 | Verfahren zur Herstellung von neuen 1,4-Benzodiazepinen bzw. ihren 4-Oxyden |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52065866A | 1966-01-14 | 1966-01-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH549585A true CH549585A (en) | 1974-05-31 |
Family
ID=24073541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH54167A CH549585A (en) | 1966-01-14 | 1967-01-11 | 1 4-benzodiazepine derivatives |
Country Status (15)
| Country | Link |
|---|---|
| JP (2) | JPS4811719B1 (en)van) |
| BE (1) | BE692621A (en)van) |
| CA (1) | CA967153A (en)van) |
| CH (1) | CH549585A (en)van) |
| CY (1) | CY669A (en)van) |
| DE (2) | DE1793682A1 (en)van) |
| DK (1) | DK124406B (en)van) |
| ES (4) | ES335613A1 (en)van) |
| FI (1) | FI47190C (en)van) |
| FR (1) | FR6110M (en)van) |
| GB (2) | GB1179124A (en)van) |
| IL (1) | IL27245A (en)van) |
| NL (1) | NL144605B (en)van) |
| NO (1) | NO120939B (en)van) |
| SE (1) | SE349806B (en)van) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4410328B2 (ja) * | 1998-12-14 | 2010-02-03 | 久光製薬株式会社 | オキソクアゼパムの製造方法 |
-
1967
- 1967-01-11 IL IL2724567A patent/IL27245A/en unknown
- 1967-01-11 CH CH54167A patent/CH549585A/de not_active IP Right Cessation
- 1967-01-13 DE DE19671793682 patent/DE1793682A1/de active Pending
- 1967-01-13 FI FI9067A patent/FI47190C/fi active
- 1967-01-13 BE BE692621D patent/BE692621A/xx not_active IP Right Cessation
- 1967-01-13 FR FR91019A patent/FR6110M/fr not_active Expired
- 1967-01-13 DE DE1967SC040084 patent/DE1695841C3/de not_active Expired
- 1967-01-13 CA CA980,377A patent/CA967153A/en not_active Expired
- 1967-01-13 GB GB189867A patent/GB1179124A/en not_active Expired
- 1967-01-13 ES ES335613A patent/ES335613A1/es not_active Expired
- 1967-01-13 NL NL6700585A patent/NL144605B/xx not_active IP Right Cessation
- 1967-01-13 GB GB4699369A patent/GB1179125A/en not_active Expired
- 1967-01-13 SE SE55167A patent/SE349806B/xx unknown
- 1967-01-13 NO NO16637667A patent/NO120939B/no unknown
- 1967-01-13 DK DK21767A patent/DK124406B/da not_active IP Right Cessation
- 1967-11-16 ES ES347271A patent/ES347271A1/es not_active Expired
- 1967-11-16 ES ES347269A patent/ES347269A1/es not_active Expired
- 1967-11-16 ES ES347270A patent/ES347270A1/es not_active Expired
-
1969
- 1969-05-21 JP JP3907469A patent/JPS4811719B1/ja active Pending
-
1970
- 1970-07-17 JP JP6220970A patent/JPS5224036B1/ja active Pending
-
1973
- 1973-01-18 CY CY66973A patent/CY669A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5224036B1 (en)van) | 1977-06-28 |
| DE1695841C3 (de) | 1980-10-02 |
| DE1793682A1 (de) | 1972-11-09 |
| DK124406B (da) | 1972-10-16 |
| CY669A (en) | 1973-01-18 |
| GB1179125A (en) | 1970-01-28 |
| NL6700585A (en)van) | 1967-07-17 |
| BE692621A (en)van) | 1967-07-13 |
| JPS4811719B1 (en)van) | 1973-04-14 |
| IL27245A (en) | 1972-08-30 |
| ES347271A1 (es) | 1969-01-16 |
| FI47190C (fi) | 1973-10-10 |
| CA967153A (en) | 1975-05-06 |
| NL144605B (nl) | 1975-01-15 |
| SE349806B (en)van) | 1972-10-09 |
| ES335613A1 (es) | 1968-03-16 |
| ES347269A1 (es) | 1969-01-16 |
| DE1695841B2 (de) | 1980-01-31 |
| FI47190B (en)van) | 1973-07-02 |
| DE1695841A1 (de) | 1972-02-03 |
| FR6110M (en)van) | 1968-06-17 |
| ES347270A1 (es) | 1969-01-16 |
| GB1179124A (en) | 1970-01-28 |
| NO120939B (en)van) | 1970-12-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |