JPH0329795B2 - - Google Patents
Info
- Publication number
- JPH0329795B2 JPH0329795B2 JP61076422A JP7642286A JPH0329795B2 JP H0329795 B2 JPH0329795 B2 JP H0329795B2 JP 61076422 A JP61076422 A JP 61076422A JP 7642286 A JP7642286 A JP 7642286A JP H0329795 B2 JPH0329795 B2 JP H0329795B2
- Authority
- JP
- Japan
- Prior art keywords
- compounds
- benzodiazepine
- formula
- compound
- cyclopropyl
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims description 71
- 238000000034 method Methods 0.000 claims description 25
- 229940049706 benzodiazepine Drugs 0.000 claims description 9
- YZIWCURGXWGKPE-UHFFFAOYSA-N 3-(5-cyclopropyl-1,2,4-oxadiazol-3-yl)-5-methyl-4h-imidazo[1,5-a][1,4]benzodiazepin-6-one Chemical compound N1=CN2C3=CC=CC=C3C(=O)N(C)CC2=C1C(N=1)=NOC=1C1CC1 YZIWCURGXWGKPE-UHFFFAOYSA-N 0.000 claims description 7
- 239000001961 anticonvulsive agent Substances 0.000 claims description 7
- 208000015114 central nervous system disease Diseases 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000002249 anxiolytic agent Substances 0.000 claims description 6
- 150000001557 benzodiazepines Chemical class 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 230000001773 anti-convulsant effect Effects 0.000 claims description 4
- 229960003965 antiepileptics Drugs 0.000 claims description 4
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- 241000699670 Mus sp. Species 0.000 description 19
- 238000012360 testing method Methods 0.000 description 17
- -1 benzodiazepine compound Chemical class 0.000 description 15
- 239000000126 substance Substances 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- 102000004300 GABA-A Receptors Human genes 0.000 description 11
- 108090000839 GABA-A Receptors Proteins 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 239000008194 pharmaceutical composition Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 230000027455 binding Effects 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 206010010904 Convulsion Diseases 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 208000019901 Anxiety disease Diseases 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 206010043994 Tonic convulsion Diseases 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000036506 anxiety Effects 0.000 description 6
- 230000000949 anxiolytic effect Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 206010053398 Clonic convulsion Diseases 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 210000003169 central nervous system Anatomy 0.000 description 5
- 230000036461 convulsion Effects 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229960005152 pentetrazol Drugs 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 230000009870 specific binding Effects 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000000543 intermediate 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
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940125681 anticonvulsant agent Drugs 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000000460 chlorine Chemical group 0.000 description 3
- 230000002566 clonic effect Effects 0.000 description 3
- 238000004590 computer program Methods 0.000 description 3
- 230000002920 convulsive effect Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 2
- XHBHKHBUALFEOU-UHFFFAOYSA-N 4,5-dihydroimidazo[1,5-a][1,4]benzodiazepin-6-one Chemical class O=C1NCC2=CN=CN2C2=CC=CC=C12 XHBHKHBUALFEOU-UHFFFAOYSA-N 0.000 description 2
- OUVUFAZUKYKNCJ-UHFFFAOYSA-N 4-imidazo[4,5-i][1,2]benzodiazepin-3-yloxadiazole Chemical class N=1N=C2C3=NC=NC3=CC=C2C=CC=1C1=CON=N1 OUVUFAZUKYKNCJ-UHFFFAOYSA-N 0.000 description 2
- BGHGVAKKIBOJGS-UHFFFAOYSA-N 5-cyclopropyl-3-(isocyanomethyl)-1,2,4-oxadiazole Chemical compound [C-]#[N+]CC1=NOC(C2CC2)=N1 BGHGVAKKIBOJGS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 102000005915 GABA Receptors Human genes 0.000 description 2
- 108010005551 GABA Receptors Proteins 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- 238000011785 NMRI mouse Methods 0.000 description 2
- 206010034759 Petit mal epilepsy Diseases 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 229940005530 anxiolytics Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000003310 benzodiazepinyl group Chemical group N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- DGBIGWXXNGSACT-UHFFFAOYSA-N clonazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl DGBIGWXXNGSACT-UHFFFAOYSA-N 0.000 description 2
- 229960003120 clonazepam Drugs 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- LDDOSDVZPSGLFZ-UHFFFAOYSA-N ethyl cyclopropanecarboxylate Chemical compound CCOC(=O)C1CC1 LDDOSDVZPSGLFZ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229960002200 flunitrazepam Drugs 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- MXGGFRZLFWXRSD-UHFFFAOYSA-N n'-hydroxy-5-methyl-6-oxo-4h-imidazo[1,5-a][1,4]benzodiazepine-3-carboximidamide Chemical compound O=C1N(C)CC2=C(C(\N)=N\O)N=CN2C2=CC=CC=C21 MXGGFRZLFWXRSD-UHFFFAOYSA-N 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 229940107390 pentasol Drugs 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 210000004129 prosencephalon Anatomy 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical class N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 description 1
- ZSJUKDUHDOMINL-UHFFFAOYSA-N 3-(1H-1,2-benzodiazepin-3-yl)-1,2,4-oxadiazole Chemical class C1=CC2=CC=CC=C2NN=C1C=1N=CON=1 ZSJUKDUHDOMINL-UHFFFAOYSA-N 0.000 description 1
- SADOJDRAQISFAK-UHFFFAOYSA-N 4-(1H-1,2-benzodiazepin-3-yl)oxadiazole Chemical class C1=CC2=CC=CC=C2NN=C1C1=CON=N1 SADOJDRAQISFAK-UHFFFAOYSA-N 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- BEGOWLXWPNPRSK-UHFFFAOYSA-N O1N=NC(=C1)C1=NC=CC=2C3=CC=CC=C3NC12 Chemical class O1N=NC(=C1)C1=NC=CC=2C3=CC=CC=C3NC12 BEGOWLXWPNPRSK-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
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- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 1
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- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
- 229960003529 diazepam Drugs 0.000 description 1
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- 231100000673 dose–response relationship Toxicity 0.000 description 1
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- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- OYPIXUZKTODLAC-UHFFFAOYSA-N n-[(5-cyclopropyl-1,2,4-oxadiazol-3-yl)methyl]formamide Chemical compound O=CNCC1=NOC(C2CC2)=N1 OYPIXUZKTODLAC-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- 239000012074 organic phase Substances 0.000 description 1
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- 150000004866 oxadiazoles Chemical class 0.000 description 1
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- 238000007911 parenteral administration Methods 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
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- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
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- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK2204/85 | 1985-05-17 | ||
| DK220485A DK220485D0 (da) | 1985-05-17 | 1985-05-17 | Nye oxadiazolylimidazobenzodiazepinderivater samt fremgangsmaade tilfremstilling heraf |
| DK3659/85 | 1985-08-12 | ||
| DK4769/85 | 1985-10-17 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1065783A Division JPH01279877A (ja) | 1985-05-17 | 1989-03-17 | ５―シクロプロピル―３―イソシアノメチル―１，２，４―オキサジアゾール |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6293289A JPS6293289A (ja) | 1987-04-28 |
| JPH0329795B2 true JPH0329795B2 (ko) | 1991-04-25 |
Family
ID=8110769
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61076422A Granted JPS6293289A (ja) | 1985-05-17 | 1986-04-02 | オキサジアゾリルイミダゾベンゾジアゼピン及びその合成法，並びに抗けいれん及び抗不安剤 |
| JP8788386A Granted JPS61263979A (ja) | 1985-05-17 | 1986-04-16 | オキサジアゾリルイミダゾベンゾジアゼピン、並びに抗けいれん及び抗不安剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8788386A Granted JPS61263979A (ja) | 1985-05-17 | 1986-04-16 | オキサジアゾリルイミダゾベンゾジアゼピン、並びに抗けいれん及び抗不安剤 |
Country Status (3)
| Country | Link |
|---|---|
| JP (2) | JPS6293289A (ko) |
| DK (1) | DK220485D0 (ko) |
| ZA (2) | ZA863574B (ko) |
-
1985
- 1985-05-17 DK DK220485A patent/DK220485D0/da unknown
-
1986
- 1986-04-02 JP JP61076422A patent/JPS6293289A/ja active Granted
- 1986-04-16 JP JP8788386A patent/JPS61263979A/ja active Granted
- 1986-05-14 ZA ZA863574A patent/ZA863574B/xx unknown
- 1986-05-14 ZA ZA863573A patent/ZA863573B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA863574B (en) | 1987-01-28 |
| JPH0127074B2 (ko) | 1989-05-26 |
| JPS61263979A (ja) | 1986-11-21 |
| DK220485D0 (da) | 1985-05-17 |
| JPS6293289A (ja) | 1987-04-28 |
| ZA863573B (en) | 1987-01-28 |
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