CH590246A5 - 7-acyl-5-phenyl-2h-1, 4-benzodiazepin-2-ones - as sedatives muscle relaxants and anticonvulsants - Google Patents
7-acyl-5-phenyl-2h-1, 4-benzodiazepin-2-ones - as sedatives muscle relaxants and anticonvulsantsInfo
- Publication number
- CH590246A5 CH590246A5 CH1740171A CH999776A CH590246A5 CH 590246 A5 CH590246 A5 CH 590246A5 CH 1740171 A CH1740171 A CH 1740171A CH 999776 A CH999776 A CH 999776A CH 590246 A5 CH590246 A5 CH 590246A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- methyl
- hydrogen
- benzodiazepin
- acid
- Prior art date
Links
- 239000001961 anticonvulsive agent Substances 0.000 title description 2
- 239000000932 sedative agent Substances 0.000 title description 2
- 229940125681 anticonvulsant agent Drugs 0.000 title 1
- 229940035363 muscle relaxants Drugs 0.000 title 1
- 239000003158 myorelaxant agent Substances 0.000 title 1
- 229940125723 sedative agent Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 239000012965 benzophenone Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 229910052731 fluorine Chemical group 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 3
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 abstract description 7
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 7
- 150000001204 N-oxides Chemical class 0.000 abstract 3
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract 2
- 229960001413 acetanilide Drugs 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000002118 epoxides Chemical class 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 238000006303 photolysis reaction Methods 0.000 abstract 1
- 230000015843 photosynthesis, light reaction Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- -1 hydrocarbon radicals Chemical class 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QPHDTFZGPWWPIU-UHFFFAOYSA-N 1-(4-amino-3-benzoylphenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C(C(=O)C=2C=CC=CC=2)=C1 QPHDTFZGPWWPIU-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UIOAQJNADLELPQ-UHFFFAOYSA-N C[C]1OCCO1 Chemical group C[C]1OCCO1 UIOAQJNADLELPQ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- IDVPXBIYMFWUEF-UHFFFAOYSA-N [2-amino-5-(2-methyl-1,3-dioxolan-2-yl)phenyl]-phenylmethanone Chemical compound C=1C=C(N)C(C(=O)C=2C=CC=CC=2)=CC=1C1(C)OCCO1 IDVPXBIYMFWUEF-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 2
- HHXVQNVADPECCD-UHFFFAOYSA-N 2-methyl-2-(4-nitrophenyl)-1,3-dioxolane Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C1(C)OCCO1 HHXVQNVADPECCD-UHFFFAOYSA-N 0.000 description 2
- FPAYKYJXGJCDFK-UHFFFAOYSA-N 7-acetyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(C(=O)C)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 FPAYKYJXGJCDFK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VQFCWDRAGUGXCP-UHFFFAOYSA-N 1-(3-phenyl-2,1-benzoxazol-5-yl)ethanone Chemical compound C=12C=C(C(=O)C)C=CC2=NOC=1C1=CC=CC=C1 VQFCWDRAGUGXCP-UHFFFAOYSA-N 0.000 description 1
- VZKHNHFKCYIECH-UHFFFAOYSA-N 1-(4-amino-3-benzoylphenyl)butan-1-one Chemical compound NC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)C(CCC)=O VZKHNHFKCYIECH-UHFFFAOYSA-N 0.000 description 1
- URWUTTPFRHIVLD-UHFFFAOYSA-N 1-(4-amino-3-benzoylphenyl)propan-1-one Chemical compound NC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)C(CC)=O URWUTTPFRHIVLD-UHFFFAOYSA-N 0.000 description 1
- DNTFLDCOLWOXKK-UHFFFAOYSA-N 1-[3-benzoyl-4-(methylamino)phenyl]ethanone Chemical compound C(C)(=O)C=1C=CC(=C(C(=O)C2=CC=CC=C2)C1)NC DNTFLDCOLWOXKK-UHFFFAOYSA-N 0.000 description 1
- YTQIJJFASBXNPD-UHFFFAOYSA-N 1-[4-amino-3-(2-fluorobenzoyl)phenyl]ethanone Chemical compound NC1=C(C(=O)C2=C(C=CC=C2)F)C=C(C=C1)C(C)=O YTQIJJFASBXNPD-UHFFFAOYSA-N 0.000 description 1
- FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 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
- IVLXQGJVBGMLRR-UHFFFAOYSA-N 2-aminoacetic acid;hydron;chloride Chemical compound Cl.NCC(O)=O IVLXQGJVBGMLRR-UHFFFAOYSA-N 0.000 description 1
- PCMWVURKIXMPLA-UHFFFAOYSA-N 2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepine-7-carbaldehyde Chemical compound C12=CC(C=O)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 PCMWVURKIXMPLA-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UFWNOIMKWNGRSJ-UHFFFAOYSA-N 3-benzoyl-4-(methylamino)benzaldehyde Chemical compound CNC1=CC=C(C=O)C=C1C(=O)C1=CC=CC=C1 UFWNOIMKWNGRSJ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- RABWNKKDNQNLCP-UHFFFAOYSA-N 4-amino-3-benzoylbenzaldehyde Chemical compound NC1=CC=C(C=O)C=C1C(=O)C1=CC=CC=C1 RABWNKKDNQNLCP-UHFFFAOYSA-N 0.000 description 1
- YQYGPGKTNQNXMH-UHFFFAOYSA-N 4-nitroacetophenone Chemical compound CC(=O)C1=CC=C([N+]([O-])=O)C=C1 YQYGPGKTNQNXMH-UHFFFAOYSA-N 0.000 description 1
- NPRKPMGGWYKYRS-UHFFFAOYSA-N 5-(2-methyl-1,3-dioxolan-2-yl)-3-phenyl-2,1-benzoxazole Chemical compound C1=CC2=NOC(C=3C=CC=CC=3)=C2C=C1C1(C)OCCO1 NPRKPMGGWYKYRS-UHFFFAOYSA-N 0.000 description 1
- IFPLKLPCDRAOIM-UHFFFAOYSA-N 5-phenyl-7-propanoyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C(CC)(=O)C=1C=CC2=C(C(=NCC(N2)=O)C2=CC=CC=C2)C1 IFPLKLPCDRAOIM-UHFFFAOYSA-N 0.000 description 1
- ZKQYDQWRGPUGRT-UHFFFAOYSA-N 7-acetyl-1-methyl-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(C)C2=CC=C(C(C)=O)C=C2C=1C1=CC=CC=C1 ZKQYDQWRGPUGRT-UHFFFAOYSA-N 0.000 description 1
- YIKGZSNQIIUVSI-UHFFFAOYSA-N 7-acetyl-5-(2-fluorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(C(=O)C)=CC=C2NC(=O)CN=C1C1=CC=CC=C1F YIKGZSNQIIUVSI-UHFFFAOYSA-N 0.000 description 1
- XOPGHUNHKBUBIE-UHFFFAOYSA-N 7-acetyl-5-(2-fluorophenyl)-3-methyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(C(C)=O)=CC=C2NC(=O)C(C)N=C1C1=CC=CC=C1F XOPGHUNHKBUBIE-UHFFFAOYSA-N 0.000 description 1
- WIIAFOUFGPBRJE-UHFFFAOYSA-N 7-pentanoyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C(CCCC)(=O)C=1C=CC2=C(C(=NCC(N2)=O)C2=CC=CC=C2)C1 WIIAFOUFGPBRJE-UHFFFAOYSA-N 0.000 description 1
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- 230000001773 anti-convulsant effect Effects 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 229940008406 diethyl sulfate Drugs 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
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- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
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- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
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- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- IMLAPXMJROBNSS-UHFFFAOYSA-N methyl 4-(1,1-dioxo-1,4-thiazinan-4-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1N1CCS(=O)(=O)CC1 IMLAPXMJROBNSS-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012430 organic reaction media Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 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
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10118370A | 1970-12-23 | 1970-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH590246A5 true CH590246A5 (en) | 1977-07-29 |
Family
ID=22283397
Family Applications (8)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1740171A CH590246A5 (en) | 1970-12-23 | 1976-08-05 | 7-acyl-5-phenyl-2h-1, 4-benzodiazepin-2-ones - as sedatives muscle relaxants and anticonvulsants |
| CH1740171A CH590250A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-23 | 1976-08-05 | |
| CH999976A CH594639A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-23 | 1976-08-05 | |
| CH1740171A CH590247A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-23 | 1976-08-05 | |
| CH1740171A CH590249A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-23 | 1976-08-05 | |
| CH1740171A CH590251A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-23 | 1976-08-05 | |
| CH1740171A CH590248A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-23 | 1976-08-05 | |
| CH1000476A CH597202A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-23 | 1976-08-05 |
Family Applications After (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1740171A CH590250A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-23 | 1976-08-05 | |
| CH999976A CH594639A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-23 | 1976-08-05 | |
| CH1740171A CH590247A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-23 | 1976-08-05 | |
| CH1740171A CH590249A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-23 | 1976-08-05 | |
| CH1740171A CH590251A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-23 | 1976-08-05 | |
| CH1740171A CH590248A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-23 | 1976-08-05 | |
| CH1000476A CH597202A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1970-12-23 | 1976-08-05 |
Country Status (4)
-
1971
- 1971-11-24 AU AU36090/71A patent/AU3609071A/en not_active Expired
- 1971-12-14 ZA ZA718349A patent/ZA718349B/xx unknown
-
1976
- 1976-08-05 CH CH1740171A patent/CH590246A5/de not_active IP Right Cessation
- 1976-08-05 CH CH1740171A patent/CH590250A5/xx not_active IP Right Cessation
- 1976-08-05 CH CH999976A patent/CH594639A5/xx not_active IP Right Cessation
- 1976-08-05 CH CH1740171A patent/CH590247A5/xx not_active IP Right Cessation
- 1976-08-05 CH CH1740171A patent/CH590249A5/xx not_active IP Right Cessation
- 1976-08-05 CH CH1740171A patent/CH590251A5/xx not_active IP Right Cessation
- 1976-08-05 CH CH1740171A patent/CH590248A5/xx not_active IP Right Cessation
- 1976-08-05 CH CH1000476A patent/CH597202A5/xx not_active IP Right Cessation
-
1978
- 1978-10-03 YU YU2328/78A patent/YU34687B/xx unknown
- 1978-10-03 YU YU2329/78A patent/YU34588B/xx unknown
- 1978-10-03 YU YU2327/78A patent/YU34686B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU34686B (en) | 1979-12-31 |
| CH590250A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-07-29 |
| CH590248A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-07-29 |
| YU34687B (en) | 1979-12-31 |
| YU232778A (en) | 1979-07-10 |
| CH590247A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-07-29 |
| CH590249A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-07-29 |
| YU232878A (en) | 1979-07-10 |
| CH590251A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-07-29 |
| YU232978A (en) | 1979-04-30 |
| YU34588B (en) | 1979-10-31 |
| CH594639A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-01-13 |
| AU3609071A (en) | 1973-05-31 |
| CH597202A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-03-31 |
| ZA718349B (en) | 1972-09-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |