CA1070302A - Substituted benzodiazepin-10-ones and method of use - Google Patents
Substituted benzodiazepin-10-ones and method of useInfo
- Publication number
- CA1070302A CA1070302A CA245,510A CA245510A CA1070302A CA 1070302 A CA1070302 A CA 1070302A CA 245510 A CA245510 A CA 245510A CA 1070302 A CA1070302 A CA 1070302A
- Authority
- CA
- Canada
- Prior art keywords
- thieno
- methyl
- benzodiazepine
- formula
- piperazinyl
- 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
- 238000000034 method Methods 0.000 title claims description 30
- 229940049706 benzodiazepine Drugs 0.000 claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims description 61
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 25
- 150000001412 amines Chemical class 0.000 claims description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 7
- XIFAUZMRAGNDGG-UHFFFAOYSA-N 10-methyl-4-(4-methylpiperazin-1-yl)thieno[3,4-b][1,5]benzodiazepine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2N(C)C2=CSC=C12 XIFAUZMRAGNDGG-UHFFFAOYSA-N 0.000 claims description 6
- IESNLGIRRRBXHI-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-10h-thieno[3,4-b][1,5]benzodiazepine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=CSC=C12 IESNLGIRRRBXHI-UHFFFAOYSA-N 0.000 claims description 6
- -1 methylthio, methylsulfonyl Chemical group 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- HHRNIDJESKFOTR-UHFFFAOYSA-N 4-methylsulfanyl-10h-thieno[3,4-b][1,5]benzodiazepine Chemical compound CSC1=NC2=CC=CC=C2NC2=CSC=C12 HHRNIDJESKFOTR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- RPOZRSGRTCYDHA-UHFFFAOYSA-N 4-piperazin-1-yl-10h-thieno[3,4-b][1,5]benzodiazepine Chemical compound C1CNCCN1C1=NC2=CC=CC=C2NC2=CSC=C12 RPOZRSGRTCYDHA-UHFFFAOYSA-N 0.000 claims description 4
- KOCCKIVKQCCVIN-UHFFFAOYSA-N 7-chloro-4-(4-methylpiperazin-1-yl)-10h-thieno[3,4-b][1,5]benzodiazepine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CSC=C12 KOCCKIVKQCCVIN-UHFFFAOYSA-N 0.000 claims description 4
- NMKAVWBKQWPLJC-UHFFFAOYSA-N 4-piperidin-1-yl-10h-thieno[3,4-b][1,5]benzodiazepine Chemical compound C1CCCCN1C1=NC2=CC=CC=C2NC2=CSC=C12 NMKAVWBKQWPLJC-UHFFFAOYSA-N 0.000 claims description 3
- NAXJLGDDFZSBFY-UHFFFAOYSA-N 7-chloro-4-methylsulfanyl-10h-thieno[3,4-b][1,5]benzodiazepine Chemical compound CSC1=NC2=CC(Cl)=CC=C2NC2=CSC=C12 NAXJLGDDFZSBFY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 3
- DWCSXQCXXITVKE-UHFFFAOYSA-N triethyloxidanium Chemical compound CC[O+](CC)CC DWCSXQCXXITVKE-UHFFFAOYSA-N 0.000 claims description 3
- YVOYIFNUIICLDB-UHFFFAOYSA-N 10-methyl-4-methylsulfanylthieno[3,4-b][1,5]benzodiazepine Chemical compound CSC1=NC2=CC=CC=C2N(C)C2=CSC=C12 YVOYIFNUIICLDB-UHFFFAOYSA-N 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 3
- SQMAXHXDGPAQLM-UHFFFAOYSA-N 7-chloro-10-methyl-4-(4-methylpiperazin-1-yl)thieno[3,4-b][1,5]benzodiazepine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2N(C)C2=CSC=C12 SQMAXHXDGPAQLM-UHFFFAOYSA-N 0.000 claims 2
- VRTVVHRYCJHXOF-UHFFFAOYSA-N 8-chloro-4-(4-methylpiperazin-1-yl)-10h-thieno[3,4-b][1,5]benzodiazepine Chemical compound C1CN(C)CCN1C1=NC2=CC=C(Cl)C=C2NC2=CSC=C12 VRTVVHRYCJHXOF-UHFFFAOYSA-N 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- GOPANLAOJZPRDF-UHFFFAOYSA-N 7-chloro-10-methyl-4-methylsulfanylthieno[3,4-b][1,5]benzodiazepine Chemical compound CSC1=NC2=CC(Cl)=CC=C2N(C)C2=CSC=C12 GOPANLAOJZPRDF-UHFFFAOYSA-N 0.000 claims 1
- SNELGSBYQRDESE-UHFFFAOYSA-N 8-chloro-4-methylsulfanyl-10h-thieno[3,4-b][1,5]benzodiazepine Chemical compound CSC1=NC2=CC=C(Cl)C=C2NC2=CSC=C12 SNELGSBYQRDESE-UHFFFAOYSA-N 0.000 claims 1
- 239000003176 neuroleptic agent Substances 0.000 abstract description 5
- 230000000202 analgesic effect Effects 0.000 abstract description 4
- 230000000701 neuroleptic effect Effects 0.000 abstract description 2
- 150000001557 benzodiazepines Chemical class 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 105
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- 239000000243 solution Substances 0.000 description 77
- 238000002360 preparation method Methods 0.000 description 56
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 55
- 239000000203 mixture Substances 0.000 description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- 239000007787 solid Substances 0.000 description 38
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- 239000013078 crystal Substances 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 238000010992 reflux Methods 0.000 description 31
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
- 229960000583 acetic acid Drugs 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 17
- 239000002244 precipitate Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000908 ammonium hydroxide Substances 0.000 description 14
- 239000012362 glacial acetic acid Substances 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 241000700159 Rattus Species 0.000 description 12
- 238000007792 addition Methods 0.000 description 12
- 239000000725 suspension Substances 0.000 description 12
- 229960004756 ethanol Drugs 0.000 description 11
- 235000019441 ethanol Nutrition 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 10
- 235000011054 acetic acid Nutrition 0.000 description 9
- 239000010410 layer Substances 0.000 description 9
- LEAKUJFYXNILRB-UHFFFAOYSA-N methyl 4-oxothiolane-3-carboxylate Chemical compound COC(=O)C1CSCC1=O LEAKUJFYXNILRB-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
- 229960000443 hydrochloric acid Drugs 0.000 description 8
- 235000011167 hydrochloric acid Nutrition 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 description 8
- 206010015995 Eyelid ptosis Diseases 0.000 description 7
- 229940093499 ethyl acetate Drugs 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 7
- 201000003004 ptosis Diseases 0.000 description 7
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- 239000000306 component Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000003929 acidic solution Substances 0.000 description 5
- 230000000561 anti-psychotic effect Effects 0.000 description 5
- 229940090044 injection Drugs 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 229960004592 isopropanol Drugs 0.000 description 5
- 229960005141 piperazine Drugs 0.000 description 5
- 229940093932 potassium hydroxide Drugs 0.000 description 5
- 235000011118 potassium hydroxide Nutrition 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 229940076134 benzene Drugs 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 3
- 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 3
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- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 3
- 239000000391 magnesium silicate Substances 0.000 description 3
- 229960002366 magnesium silicate Drugs 0.000 description 3
- 229910052919 magnesium silicate Inorganic materials 0.000 description 3
- 235000019792 magnesium silicate Nutrition 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
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- 230000001225 therapeutic effect Effects 0.000 description 3
- 239000012485 toluene extract Substances 0.000 description 3
- RPKCLSMBVQLWIN-UHFFFAOYSA-N 2-n-methylbenzene-1,2-diamine Chemical compound CNC1=CC=CC=C1N RPKCLSMBVQLWIN-UHFFFAOYSA-N 0.000 description 2
- VYCOLKDMMRNXKM-UHFFFAOYSA-N 3h-thieno[3,4-b][1,5]benzodiazepine Chemical compound N1=C2C=CC=CC2=NC=C2CSC=C21 VYCOLKDMMRNXKM-UHFFFAOYSA-N 0.000 description 2
- BXIXXXYDDJVHDL-UHFFFAOYSA-N 4-Chloro-ortho-phenylenediamine Chemical compound NC1=CC=C(Cl)C=C1N BXIXXXYDDJVHDL-UHFFFAOYSA-N 0.000 description 2
- UVUAKQQNONYKJK-UHFFFAOYSA-N 4-chloro-1-n-methylbenzene-1,2-diamine Chemical compound CNC1=CC=C(Cl)C=C1N UVUAKQQNONYKJK-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- IOFCETCRVXVICT-UHFFFAOYSA-N 7-fluoro-4-methylsulfanyl-10h-thieno[3,4-b][1,5]benzodiazepine Chemical compound CSC1=NC2=CC(F)=CC=C2NC2=CSC=C12 IOFCETCRVXVICT-UHFFFAOYSA-N 0.000 description 2
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- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
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- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 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 2
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- 208000011580 syndromic disease Diseases 0.000 description 2
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- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/552,022 US3951981A (en) | 1975-02-24 | 1975-02-24 | Substituted benzodiazepines and method of use |
| US05/552,023 US3953430A (en) | 1975-02-24 | 1975-02-24 | Substituted benzodiazepin-10-ones and method of use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1070302A true CA1070302A (en) | 1980-01-22 |
Family
ID=27069934
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA245,510A Expired CA1070302A (en) | 1975-02-24 | 1976-02-11 | Substituted benzodiazepin-10-ones and method of use |
Country Status (13)
-
1976
- 1976-01-28 IL IL48921A patent/IL48921A/xx unknown
- 1976-01-29 AU AU10628/76A patent/AU502678B2/en not_active Expired
- 1976-02-02 GB GB4070/76A patent/GB1534963A/en not_active Expired
- 1976-02-11 CA CA245,510A patent/CA1070302A/en not_active Expired
- 1976-02-20 NL NL7601766A patent/NL7601766A/xx not_active Application Discontinuation
- 1976-02-20 FR FR7604781A patent/FR2301261A1/fr active Pending
- 1976-02-23 SE SE7602172A patent/SE7602172L/ not_active Application Discontinuation
- 1976-02-23 RO RO7684897A patent/RO69468A/ro unknown
- 1976-02-23 DE DE19762607295 patent/DE2607295A1/de not_active Withdrawn
- 1976-02-24 JP JP51019373A patent/JPS51110599A/ja active Pending
- 1976-02-24 DD DD191446A patent/DD125578A5/xx unknown
- 1976-02-24 ES ES445474A patent/ES445474A1/es not_active Expired
-
1977
- 1977-04-18 ES ES457913A patent/ES457913A1/es not_active Expired
-
1979
- 1979-12-27 HK HK878/79A patent/HK87879A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7601766A (nl) | 1976-08-26 |
| FR2301261A1 (fr) | 1976-09-17 |
| HK87879A (en) | 1980-01-04 |
| SE7602172L (sv) | 1976-11-25 |
| GB1534963A (en) | 1978-12-06 |
| ES457913A1 (es) | 1978-07-16 |
| IL48921A (en) | 1979-10-31 |
| AU502678B2 (en) | 1979-08-02 |
| DE2607295A1 (de) | 1976-09-02 |
| IL48921A0 (en) | 1976-03-31 |
| ES445474A1 (es) | 1977-10-16 |
| RO69468A (ro) | 1982-04-12 |
| JPS51110599A (enrdf_load_stackoverflow) | 1976-09-30 |
| DD125578A5 (enrdf_load_stackoverflow) | 1977-05-04 |
| AU1062876A (en) | 1977-08-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |