DE2165311A1 - Neue 1-aryl-3h-1,4-benzodiazepin2,5-(1h,4h)-dione - Google Patents
Neue 1-aryl-3h-1,4-benzodiazepin2,5-(1h,4h)-dioneInfo
- Publication number
- DE2165311A1 DE2165311A1 DE2165311A DE2165311A DE2165311A1 DE 2165311 A1 DE2165311 A1 DE 2165311A1 DE 2165311 A DE2165311 A DE 2165311A DE 2165311 A DE2165311 A DE 2165311A DE 2165311 A1 DE2165311 A1 DE 2165311A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- phenyl
- dione
- benzodiazepine
- pharmaceutical
- 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
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000004480 active ingredient Substances 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- -1 I 1 iuor Substances 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 claims 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000008120 corn starch Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 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
- 238000003756 stirring Methods 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
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- 230000000694 effects Effects 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
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- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940113088 dimethylacetamide Drugs 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-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
- QQUIWIVTEWQHKA-UHFFFAOYSA-N 3h-1,4-benzodiazepine Chemical compound C1=NCC=NC2=CC=CC=C21 QQUIWIVTEWQHKA-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229940096529 carboxypolymethylene Drugs 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- LXMQZGGLHVSEBA-UHFFFAOYSA-N chromium;trihydrate Chemical compound O.O.O.[Cr] LXMQZGGLHVSEBA-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 238000005304 joining Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- KFOPKOFKGJJEBW-ZSSYTAEJSA-N methyl 2-[(1s,7r,8s,9s,10r,13r,14s,17r)-1,7-dihydroxy-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]acetate Chemical compound C([C@H]1O)C2=CC(=O)C[C@H](O)[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](CC(=O)OC)[C@@]1(C)CC2 KFOPKOFKGJJEBW-ZSSYTAEJSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
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- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
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- 238000005303 weighing Methods 0.000 description 1
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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
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Priority Applications (33)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE793460D BE793460A (fr) | 1971-12-29 | Nouvelles 1-aryl-3h,1,4-benzodiazepine-2,5-(1h | |
| DE2165311A DE2165311A1 (de) | 1971-12-29 | 1971-12-29 | Neue 1-aryl-3h-1,4-benzodiazepin2,5-(1h,4h)-dione |
| RO7200073207A RO62852A (fr) | 1971-12-29 | 1972-12-19 | Procede pour la preparation des 1-aryle-3h-1,4-benzodiazepin-2,5(1h,4h)-diones |
| AT228574*1A AT324345B (de) | 1971-12-29 | 1972-12-19 | Verfahren zur herstellung neuer 1-aryl-3h-1,4-benzodiazepin-2,5-(1h,4h)-dione |
| AT1080772A AT327912B (de) | 1971-12-29 | 1972-12-19 | Verfahren zur herstellung neuer 1-aryl-3h-1,4-benzodiazepin-2,5- (1h,4h) -dione |
| SU1860137*7A SU452098A3 (ru) | 1971-12-29 | 1972-12-20 | Способ получени 1-арил-3н-1,4 -бензодиазепин-2,5-(1н,4н)-дионов |
| SU1955543A SU461502A3 (ru) | 1971-12-29 | 1972-12-20 | Способ получени 1-арил-3н-1, 4-бензодиазепин-2,5-(1н,4н)дионов |
| DK641872AA DK129655B (da) | 1971-12-29 | 1972-12-21 | Analogifremgangsmåde til fremstilling af 1-aryl-3H-1,4-benzodiazepin-2,5-(1H,4H)-dioner. |
| JP47129704A JPS4885587A (enrdf_load_stackoverflow) | 1971-12-29 | 1972-12-26 | |
| BG022240A BG19805A3 (bg) | 1971-12-29 | 1972-12-26 | Метод за получаване на 1-арил-3н-1,4-бензодиазепин-2,5- (1н,4н)диони |
| BG025578A BG20375A3 (bg) | 1971-12-29 | 1972-12-26 | Метод за получаване на 1-арил-3н-1,4-бензодиазепин- 2,5-(1н,4н)-диони |
| ES410057A ES410057A1 (es) | 1971-12-29 | 1972-12-27 | Procedimiento para la preparacion de nuevas 1-aril-3h1,4- benzodiazepin-2,5-(1h, 4h)-dionas. |
| DD168055*A DD106384A5 (enrdf_load_stackoverflow) | 1971-12-29 | 1972-12-27 | |
| ZA729073A ZA729073B (en) | 1971-12-29 | 1972-12-27 | Improvements relating to benzodiazepines |
| CH250676A CH583208A5 (enrdf_load_stackoverflow) | 1971-12-29 | 1972-12-27 | |
| CH1887672A CH587830A5 (enrdf_load_stackoverflow) | 1971-12-29 | 1972-12-27 | |
| NO4808/72A NO138089C (no) | 1971-12-29 | 1972-12-28 | Analogifremgangsmaate for fremstilling av terapeutisk aktive benzodiazepinderivater |
| SE7217089A SE405120B (sv) | 1971-12-29 | 1972-12-28 | Analogiforfarande for framstellning av 1-aryl-1,4-bensodiazepin-2,5-dioner |
| PL1972159831A PL85284B1 (en) | 1971-12-29 | 1972-12-28 | Benzodiazepines[au5062772a] |
| IL41198A IL41198A (en) | 1971-12-29 | 1972-12-28 | 1 - Phenyl - H3 - 1, 4 - Benzodiazepine - H1, H) - 5, 42 (- Diones, their preparation and pharmaceutical preparations containing them |
| PL1972175731A PL84244B1 (en) | 1971-12-29 | 1972-12-28 | Benzodiazepines[au5062772a] |
| HUBO5306A HU165306B (enrdf_load_stackoverflow) | 1971-12-29 | 1972-12-28 | |
| GB5988172A GB1395772A (en) | 1971-12-29 | 1972-12-28 | 1-aryl-3h-1,4-benzodiazepin-2,5-1h,4h-diones |
| FI3686/72A FI54920C (fi) | 1971-12-29 | 1972-12-28 | Foerfarande foer framstaellning av nya terapeutiskt vaerdefulla 1-aryl-3h-1,4-benzodiazepin-2,5-(1h,4h)-dioner |
| CA160,145A CA1028702A (en) | 1971-12-29 | 1972-12-28 | 1-aryl-3h-1,4-benzodiazepine-2,5-(1h,4h)-diones |
| IE1805/72A IE37815B1 (en) | 1971-12-29 | 1972-12-29 | 1-aryl-3h-1,4-benzodiazepin-2,5-(1h,4h)-diones |
| FR7247013A FR2166204B1 (enrdf_load_stackoverflow) | 1971-12-29 | 1972-12-29 | |
| AU50627/72A AU471990B2 (en) | 1971-11-24 | 1972-12-29 | 1-aryl-3h-1,4-benzodiazepin-2,5-(1h,4h)-diones |
| NL7217795A NL7217795A (enrdf_load_stackoverflow) | 1971-12-29 | 1972-12-29 | |
| US413795A US3914216A (en) | 1962-12-18 | 1973-11-08 | 1-Phenyl-3H-1,4-benzodiazepine-2,5-(1H,4H)-diones |
| PH14201*[A PH10241A (en) | 1962-12-18 | 1973-12-26 | 1-phenyl-3h-1,4-benzodiazepine-2,5-(1h,4h)-diones |
| ES425329A ES425329A1 (es) | 1971-12-29 | 1974-04-16 | Procedimiento para la reparacion de nuevas 1-aril-3h-1,4- benzodiazepin - 2,5-(1h,4h)-dionas. |
| FR7438417A FR2246403A1 (en) | 1971-11-24 | 1974-11-22 | Three piece synthetic castor - wheel halves snap together onto central body portion |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2165311A DE2165311A1 (de) | 1971-12-29 | 1971-12-29 | Neue 1-aryl-3h-1,4-benzodiazepin2,5-(1h,4h)-dione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2165311A1 true DE2165311A1 (de) | 1973-07-12 |
Family
ID=5829591
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2165311A Pending DE2165311A1 (de) | 1962-12-18 | 1971-12-29 | Neue 1-aryl-3h-1,4-benzodiazepin2,5-(1h,4h)-dione |
Country Status (23)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1319144C (en) * | 1986-11-14 | 1993-06-15 | Quirico Branca | Tetrahydronaphthalene derivatives |
| RU2687556C1 (ru) * | 2018-12-24 | 2019-05-15 | Акционерное общество "Федеральный научно-производственный центр "Алтай" | Способ получения 7-хлор-1,3-дигидро-1-метил-5-фенил-2Н-1,4-бензодиазепин-2-она |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT280290B (de) * | 1967-11-24 | 1970-04-10 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von neuen 1-Phenyl-4-alkyl-3H-1,4-benzodiazepin-2,5-[1H,4H]-dionen |
-
0
- BE BE793460D patent/BE793460A/xx unknown
-
1971
- 1971-12-29 DE DE2165311A patent/DE2165311A1/de active Pending
-
1972
- 1972-12-19 AT AT228574*1A patent/AT324345B/de not_active IP Right Cessation
- 1972-12-19 AT AT1080772A patent/AT327912B/de not_active IP Right Cessation
- 1972-12-19 RO RO7200073207A patent/RO62852A/ro unknown
- 1972-12-20 SU SU1955543A patent/SU461502A3/ru active
- 1972-12-20 SU SU1860137*7A patent/SU452098A3/ru active
- 1972-12-21 DK DK641872AA patent/DK129655B/da unknown
- 1972-12-26 BG BG022240A patent/BG19805A3/xx unknown
- 1972-12-26 JP JP47129704A patent/JPS4885587A/ja active Pending
- 1972-12-26 BG BG025578A patent/BG20375A3/xx unknown
- 1972-12-27 CH CH1887672A patent/CH587830A5/xx not_active IP Right Cessation
- 1972-12-27 CH CH250676A patent/CH583208A5/xx not_active IP Right Cessation
- 1972-12-27 ZA ZA729073A patent/ZA729073B/xx unknown
- 1972-12-27 DD DD168055*A patent/DD106384A5/xx unknown
- 1972-12-27 ES ES410057A patent/ES410057A1/es not_active Expired
- 1972-12-28 PL PL1972175731A patent/PL84244B1/pl unknown
- 1972-12-28 GB GB5988172A patent/GB1395772A/en not_active Expired
- 1972-12-28 FI FI3686/72A patent/FI54920C/fi active
- 1972-12-28 CA CA160,145A patent/CA1028702A/en not_active Expired
- 1972-12-28 PL PL1972159831A patent/PL85284B1/pl unknown
- 1972-12-28 SE SE7217089A patent/SE405120B/xx unknown
- 1972-12-28 NO NO4808/72A patent/NO138089C/no unknown
- 1972-12-28 HU HUBO5306A patent/HU165306B/hu unknown
- 1972-12-28 IL IL41198A patent/IL41198A/en unknown
- 1972-12-29 NL NL7217795A patent/NL7217795A/xx not_active Application Discontinuation
- 1972-12-29 FR FR7247013A patent/FR2166204B1/fr not_active Expired
- 1972-12-29 IE IE1805/72A patent/IE37815B1/xx unknown
-
1974
- 1974-04-16 ES ES425329A patent/ES425329A1/es not_active Expired
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