DE2163642A1 - Benzodiazepin-Derivate - Google Patents
Benzodiazepin-DerivateInfo
- Publication number
- DE2163642A1 DE2163642A1 DE19712163642 DE2163642A DE2163642A1 DE 2163642 A1 DE2163642 A1 DE 2163642A1 DE 19712163642 DE19712163642 DE 19712163642 DE 2163642 A DE2163642 A DE 2163642A DE 2163642 A1 DE2163642 A1 DE 2163642A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- dioxolan
- hydrogen
- compound
- methyl
- 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
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 title claims 5
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims description 94
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- -1 1,3-dioxolan-2-yl Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000007514 bases Chemical class 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 229910052731 fluorine Chemical group 0.000 claims description 7
- 239000011737 fluorine Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- UIOAQJNADLELPQ-UHFFFAOYSA-N C[C]1OCCO1 Chemical group C[C]1OCCO1 UIOAQJNADLELPQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000000932 sedative agent Substances 0.000 claims description 3
- 230000001624 sedative effect Effects 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 230000001773 anti-convulsant effect Effects 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 1
- 239000008141 laxative Substances 0.000 claims 1
- 230000002475 laxative effect Effects 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 230000002040 relaxant effect Effects 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- 235000019441 ethanol Nutrition 0.000 description 20
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
- 239000003960 organic solvent Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 9
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- 229920002261 Corn starch Polymers 0.000 description 7
- 229960001413 acetanilide Drugs 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000008120 corn starch Substances 0.000 description 7
- 229940099112 cornstarch Drugs 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 150000001540 azides Chemical group 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 235000009518 sodium iodide Nutrition 0.000 description 4
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 3
- 125000005543 phthalimide group Chemical group 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- YBAHFCASYBWQFV-UHFFFAOYSA-N (2-chloro-2-oxoethyl) methanesulfonate Chemical compound CS(=O)(=O)OCC(Cl)=O YBAHFCASYBWQFV-UHFFFAOYSA-N 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 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical compound O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 description 2
- HTWIZMNMTWYQRN-UHFFFAOYSA-N 2-methyl-1,3-dioxolane Chemical compound CC1OCCO1 HTWIZMNMTWYQRN-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- AGBKHDWHTYRWLE-UHFFFAOYSA-N O1C(OCC1)C=1C=CC2=C(C(=NCC(N2)=O)C2=CC=CC=C2)C1 Chemical compound O1C(OCC1)C=1C=CC2=C(C(=NCC(N2)=O)C2=CC=CC=C2)C1 AGBKHDWHTYRWLE-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- ZDNJPLSZJKKRPH-UHFFFAOYSA-N (2-methylsulfonyloxyacetyl) 2-methylsulfonyloxyacetate Chemical compound S(=O)(=O)(C)OCC(=O)OC(COS(=O)(=O)C)=O ZDNJPLSZJKKRPH-UHFFFAOYSA-N 0.000 description 1
- RIXYVXYKLYQCSM-UHFFFAOYSA-N 2-(4-nitrophenyl)-1,3-dioxolane Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1OCCO1 RIXYVXYKLYQCSM-UHFFFAOYSA-N 0.000 description 1
- SYZRZLUNWVNNNV-UHFFFAOYSA-N 2-bromoacetyl chloride Chemical compound ClC(=O)CBr SYZRZLUNWVNNNV-UHFFFAOYSA-N 0.000 description 1
- ULQQGOGMQRGFFR-UHFFFAOYSA-N 2-chlorobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=CC=C1Cl ULQQGOGMQRGFFR-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
- IHBVNSPHKMCPST-UHFFFAOYSA-N 3-bromopropanoyl chloride Chemical compound ClC(=O)CCBr IHBVNSPHKMCPST-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-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
- 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
- OZOWKVGUJMKRON-UHFFFAOYSA-N 7-(2-methyl-1,3-dioxolan-2-yl)-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C=1C=C2NC(=O)CN=C(C=3C=CC=CC=3)C2=CC=1C1(C)OCCO1 OZOWKVGUJMKRON-UHFFFAOYSA-N 0.000 description 1
- GBCGCGMGUNMJDG-UHFFFAOYSA-N CC1(C(C=C2)=CC=C2NC(C(C(C2=CC=CC=C2)=O)Cl)=O)OCCO1 Chemical compound CC1(C(C=C2)=CC=C2NC(C(C(C2=CC=CC=C2)=O)Cl)=O)OCCO1 GBCGCGMGUNMJDG-UHFFFAOYSA-N 0.000 description 1
- SEKCVCNUQDQNMI-UHFFFAOYSA-N CC1(OCCO1)C=1C=CC2=C(C(NCC(N2)=O)C2=CC=CC=C2)C1 Chemical compound CC1(OCCO1)C=1C=CC2=C(C(NCC(N2)=O)C2=CC=CC=C2)C1 SEKCVCNUQDQNMI-UHFFFAOYSA-N 0.000 description 1
- QKDOBQKZVUFOPF-UHFFFAOYSA-N CN1C(C=CC(C2OCCO2)=C2)=C2C(C2=CC=CC=C2)=NCC1 Chemical compound CN1C(C=CC(C2OCCO2)=C2)=C2C(C2=CC=CC=C2)=NCC1 QKDOBQKZVUFOPF-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- PTYUHDLQQZKFRB-UHFFFAOYSA-N ClCC(=O)NC1=C(C=C(C=C1)C1OCCO1)C(=O)C1=CC=CC=C1 Chemical compound ClCC(=O)NC1=C(C=C(C=C1)C1OCCO1)C(=O)C1=CC=CC=C1 PTYUHDLQQZKFRB-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- BRSPETQTAPCNBO-UHFFFAOYSA-N N(=[N+]=[N-])CC(=O)NC1=C(C=C(C=C1)C1(OCCO1)C)C(C1=CC=CC=C1)=O Chemical compound N(=[N+]=[N-])CC(=O)NC1=C(C=C(C=C1)C1(OCCO1)C)C(C1=CC=CC=C1)=O BRSPETQTAPCNBO-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- FARLZYCNUYJHMW-UHFFFAOYSA-N [2-(benzenesulfonyl)acetyl] 2-(benzenesulfonyl)acetate Chemical compound C1(=CC=CC=C1)S(=O)(=O)CC(=O)OC(CS(=O)(=O)C1=CC=CC=C1)=O FARLZYCNUYJHMW-UHFFFAOYSA-N 0.000 description 1
- FFCAMMUWIHPLAP-UHFFFAOYSA-N [2-amino-5-(1,3-dioxolan-2-yl)phenyl]-phenylmethanone Chemical compound NC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)C1OCCO1 FFCAMMUWIHPLAP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- UAZDIGCOBKKMPU-UHFFFAOYSA-O azanium;azide Chemical compound [NH4+].[N-]=[N+]=[N-] UAZDIGCOBKKMPU-UHFFFAOYSA-O 0.000 description 1
- DXZDEAJXVCLRLE-UHFFFAOYSA-N azepin-2-one Chemical compound O=C1C=CC=CC=N1 DXZDEAJXVCLRLE-UHFFFAOYSA-N 0.000 description 1
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000012336 iodinating agent Substances 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-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
- 239000011812 mixed powder Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- WMALWWBRYBTTHO-UHFFFAOYSA-N n-[2-benzoyl-4-(2-methyl-1,3-dioxolan-2-yl)phenyl]-2-chloroacetamide Chemical compound C=1C=C(NC(=O)CCl)C(C(=O)C=2C=CC=CC=2)=CC=1C1(C)OCCO1 WMALWWBRYBTTHO-UHFFFAOYSA-N 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 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
- 230000035484 reaction time Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10118370A | 1970-12-23 | 1970-12-23 | |
| US10111770A | 1970-12-23 | 1970-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2163642A1 true DE2163642A1 (de) | 1972-07-13 |
Family
ID=26797912
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712163522 Pending DE2163522A1 (de) | 1970-12-23 | 1971-12-21 | Benzodiazepin-Derivate |
| DE19712163642 Pending DE2163642A1 (de) | 1970-12-23 | 1971-12-21 | Benzodiazepin-Derivate |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712163522 Pending DE2163522A1 (de) | 1970-12-23 | 1971-12-21 | Benzodiazepin-Derivate |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5610310B1 (cs) |
| AR (1) | AR193632A1 (cs) |
| AT (2) | AT322556B (cs) |
| AU (1) | AU458983B2 (cs) |
| BE (2) | BE777097A (cs) |
| BG (1) | BG17804A3 (cs) |
| BR (1) | BR7108411D0 (cs) |
| CA (2) | CA935157A (cs) |
| CH (2) | CH582162A5 (cs) |
| DD (1) | DD95384A5 (cs) |
| DE (2) | DE2163522A1 (cs) |
| ES (1) | ES398222A1 (cs) |
| FR (2) | FR2119070A1 (cs) |
| GB (1) | GB1321938A (cs) |
| HU (1) | HU164249B (cs) |
| IL (1) | IL38234A0 (cs) |
| LU (1) | LU64491A1 (cs) |
| NL (3) | NL7117480A (cs) |
| PL (1) | PL83080B1 (cs) |
| RO (1) | RO70586A (cs) |
| YU (1) | YU35004B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100932093B1 (ko) | 2006-09-27 | 2009-12-16 | 주식회사종근당 | 미세소관 형성 저해제로서 유용한 벤조페논 유도체 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4833759A (cs) * | 1971-09-01 | 1973-05-12 |
-
1971
- 1971-11-26 IL IL38234A patent/IL38234A0/xx unknown
- 1971-11-30 CH CH1740171A patent/CH582162A5/xx not_active IP Right Cessation
- 1971-12-03 CA CA129226A patent/CA935157A/en not_active Expired
- 1971-12-03 CH CH1761371A patent/CH565775A5/xx not_active IP Right Cessation
- 1971-12-20 NL NL7117480A patent/NL7117480A/xx not_active Application Discontinuation
- 1971-12-20 BR BR8411/71A patent/BR7108411D0/pt unknown
- 1971-12-21 RO RO7169138A patent/RO70586A/ro unknown
- 1971-12-21 JP JP10401571A patent/JPS5610310B1/ja active Pending
- 1971-12-21 CA CA130,660A patent/CA948629A/en not_active Expired
- 1971-12-21 DE DE19712163522 patent/DE2163522A1/de active Pending
- 1971-12-21 LU LU64491A patent/LU64491A1/xx unknown
- 1971-12-21 DE DE19712163642 patent/DE2163642A1/de active Pending
- 1971-12-21 AU AU37153/71A patent/AU458983B2/en not_active Expired
- 1971-12-22 AT AT1105071A patent/AT322556B/de not_active IP Right Cessation
- 1971-12-22 AR AR239761A patent/AR193632A1/es active
- 1971-12-22 ES ES398222A patent/ES398222A1/es not_active Expired
- 1971-12-22 BE BE777097A patent/BE777097A/xx unknown
- 1971-12-22 DD DD159822A patent/DD95384A5/xx unknown
- 1971-12-22 BE BE777098A patent/BE777098A/xx unknown
- 1971-12-22 AT AT847174*1A patent/AT325628B/de not_active IP Right Cessation
- 1971-12-23 FR FR7146455A patent/FR2119070A1/fr not_active Withdrawn
- 1971-12-23 NL NL7117762A patent/NL7117762A/xx unknown
- 1971-12-23 FR FR7146456A patent/FR2154391B1/fr not_active Expired
- 1971-12-23 PL PL1971152445A patent/PL83080B1/pl unknown
- 1971-12-23 YU YU3235/71A patent/YU35004B/xx unknown
- 1971-12-23 BG BG019309A patent/BG17804A3/xx unknown
- 1971-12-23 NL NL7117760A patent/NL7117760A/xx unknown
- 1971-12-23 GB GB5998071A patent/GB1321938A/en not_active Expired
- 1971-12-23 HU HUHO1442A patent/HU164249B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2119070A1 (fr) | 1972-08-04 |
| NL7117762A (cs) | 1972-06-27 |
| YU323571A (en) | 1979-12-31 |
| DD95384A5 (cs) | 1973-02-05 |
| PL83080B1 (cs) | 1975-12-31 |
| NL7117760A (cs) | 1972-06-27 |
| AT325628B (de) | 1975-10-27 |
| BG17804A3 (bg) | 1973-12-25 |
| CA948629A (en) | 1974-06-04 |
| YU35004B (en) | 1980-06-30 |
| RO70586A (ro) | 1981-07-30 |
| CH582162A5 (cs) | 1976-11-30 |
| BR7108411D0 (pt) | 1973-06-14 |
| BE777098A (fr) | 1972-06-22 |
| GB1321938A (en) | 1973-07-04 |
| IL38234A0 (en) | 1972-01-27 |
| AT322556B (de) | 1975-05-26 |
| DE2163522A1 (de) | 1972-07-13 |
| AU458983B2 (en) | 1975-03-13 |
| JPS5610310B1 (cs) | 1981-03-06 |
| BE777097A (fr) | 1972-06-22 |
| CA935157A (en) | 1973-10-09 |
| FR2154391A1 (cs) | 1973-05-11 |
| LU64491A1 (cs) | 1973-07-16 |
| HU164249B (cs) | 1974-01-28 |
| FR2154391B1 (cs) | 1975-03-14 |
| CH565775A5 (cs) | 1975-08-29 |
| AR193632A1 (es) | 1973-05-11 |
| ES398222A1 (es) | 1975-06-01 |
| AU3715371A (en) | 1973-06-28 |
| NL7117480A (cs) | 1972-06-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3527117A1 (de) | 1-(aminophenyl)-4-(methyl)-5h-2,3-benzodiazepinderivate, verfahren zur herstellung derselben und diese enthaltende arzneimittel | |
| DE2302717A1 (de) | Heterocyclische verbindungen | |
| DE1545935A1 (de) | Verfahren zur Herstellung von Benzodiazepin-Derivaten | |
| DE2206012A1 (de) | Pharmazeutisches Präparat | |
| DE2141598A1 (de) | Benzolderivate | |
| DD203907A5 (de) | Verfahren zur herstellung von 7-brom-5-(2-halogenphenyl)-1h-2,3 dihydro-1,4-benzodiazepin-verbindungen | |
| DE1961727A1 (de) | Diazepin-Derivate | |
| DE1670305C3 (de) | 5-Phenyl-2,4-dioxo-1,2,3,4-tetrahydro-3H-1,5-benzodiazepine und Verfahren zu ihrer Herstellung | |
| CH532065A (de) | Verfahren zur Herstellung von Benzodiazepinderivaten | |
| WO1996004283A1 (de) | Neue 3-substituierte 3h-2,3-benzodiazepinderivate, deren herstellung und verwendung als arzneimittel | |
| DE2163642A1 (de) | Benzodiazepin-Derivate | |
| DE2238579A1 (de) | Benzodiazepinderivate | |
| DE1952486C2 (cs) | ||
| DE2163625A1 (de) | Benzodiazepin-Derivate | |
| DE2000775A1 (de) | Substituierte 1,2,3,4-Tetrahydrobenzothieno-[2,3-c]-pyridinderivate und Verfahren zu deren Herstellung | |
| DE2159527A1 (de) | Verfahren zur Herstellung von Diazepinderivaten und nach diesen Verfahren herstellbare neue Diazepinderivate | |
| DE2360852A1 (de) | Neue azabenzo-1,5-diazepine | |
| DE1695211A1 (de) | Verfahren zur Herstellung von Benzodiazepin-Derivaten | |
| AT311363B (de) | Verfahren zur Herstellung von neuen Benzodiazepinderivaten und ihren Säureadditionssalzen | |
| DE1947226C3 (de) | 1 l-Chlor-8,12b-dihydro-23-dimethyll2b-phenyl-4H [13] -oxazino [3,2-d] [1,4] benzodiazepin-4,7(6H)dion und Verfahren zur Herstellung dieser Verbindung | |
| CH568989A5 (en) | 7(1-hydroxyalkyl)-5-phenyl-1, 4-benzodiazepines - - as muscle relaxants sedatives and anticonvulsants | |
| DE2311714A1 (de) | Neue 1,4-benzodiazepine | |
| AT309450B (de) | Verfahren zur Herstellung von neuen Benzodiazepinderivaten und ihren Säureadditionssalzen | |
| AT332876B (de) | Verfahren zur herstellung von neuen benzodiazepin-derivaten | |
| AT309453B (de) | Verfahren zur Herstellung von neuen Benzodiazepinderivaten und ihren Säureadditionssalzen |