NO118706B - - Google Patents

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Publication number: NO118706B
Authority: NO; Norway
Prior art keywords: benzodiazepine; phenyl; chloro; ethyl; lower alkyl
Prior art date: 1963-02-19

Application number

NO152064A

Other languages

English (en)

Norwegian (no)

Inventor

E Reeder

L Sternbach

G Archer

R Fryer

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

1963-02-19

Filing date

1964-02-18

Publication date

1970-02-02

1964-02-18 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1970-02-02 Publication of NO118706B publication Critical patent/NO118706B/no

Links

150000001875 compounds Chemical class 0.000 claims description 22
-1 N-substituted piperazinyl group Chemical group 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 14
238000000034 method Methods 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims description 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
150000003335 secondary amines Chemical class 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 4
125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 1
125000005265 dialkylamine group Chemical group 0.000 claims 1
108090000623 proteins and genes Proteins 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
238000002844 melting Methods 0.000 description 42
230000008018 melting Effects 0.000 description 42
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 37
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
239000000203 mixture Substances 0.000 description 25
238000001953 recrystallisation Methods 0.000 description 21
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000007795 chemical reaction product Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
RIUVIMLHUDDDHK-UHFFFAOYSA-N 7-chloro-1-(3-chloropropyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCCl)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 RIUVIMLHUDDDHK-UHFFFAOYSA-N 0.000 description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000011976 maleic acid Substances 0.000 description 5
229940032007 methylethyl ketone Drugs 0.000 description 5
235000009518 sodium iodide Nutrition 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
ZUDOJRSIPGXDQB-UHFFFAOYSA-N 7-chloro-1-(3-chloropropyl)-5-(2-fluorophenyl)-3H-1,4-benzodiazepin-2-one Chemical compound FC1=C(C=CC=C1)C1=NCC(=O)N(CCCCl)C2=CC=C(Cl)C=C12 ZUDOJRSIPGXDQB-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
239000002253 acid Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000002904 solvent Substances 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000000284 extract Substances 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000010410 layer Substances 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
FUHISLTZXOSDOX-UHFFFAOYSA-N 7-chloro-1-[1-(dimethylamino)propan-2-yl]-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(C(CN(C)C)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 FUHISLTZXOSDOX-UHFFFAOYSA-N 0.000 description 2
JULCZDGUUXWYAA-UHFFFAOYSA-N 7-chloro-1-[1-(dimethylamino)propan-2-yl]-5-phenyl-3h-1,4-benzodiazepin-2-one;dihydrochloride Chemical compound Cl.Cl.N=1CC(=O)N(C(CN(C)C)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 JULCZDGUUXWYAA-UHFFFAOYSA-N 0.000 description 2
NDFYNPQEYIFWLP-UHFFFAOYSA-N 7-chloro-1-[2-(diethylamino)ethyl]-5-(2-fluorophenyl)-4,5-dihydro-3h-1,4-benzodiazepin-2-one Chemical compound N1CC(=O)N(CCN(CC)CC)C2=CC=C(Cl)C=C2C1C1=CC=CC=C1F NDFYNPQEYIFWLP-UHFFFAOYSA-N 0.000 description 2
RSBJJFCYTYWDLH-UHFFFAOYSA-N 7-chloro-1-[3-(diethylamino)propyl]-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCN(CC)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 RSBJJFCYTYWDLH-UHFFFAOYSA-N 0.000 description 2
ACRXWCHOYGQNEI-UHFFFAOYSA-N 7-chloro-1-[3-(diethylamino)propyl]-5-phenyl-3h-1,4-benzodiazepin-2-one;dihydrochloride Chemical compound Cl.Cl.N=1CC(=O)N(CCCN(CC)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ACRXWCHOYGQNEI-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZIIJJOPLRSCQNX-UHFFFAOYSA-N Flurazepam hydrochloride Chemical compound Cl.Cl.N=1CC(=O)N(CCN(CC)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F ZIIJJOPLRSCQNX-UHFFFAOYSA-N 0.000 description 2
MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001557 benzodiazepines Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000155 melt Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
229910003446 platinum oxide Inorganic materials 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
FIGUZKDKRDZRIW-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-7-nitro-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCN(C)C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 FIGUZKDKRDZRIW-UHFFFAOYSA-N 0.000 description 1
GPTVQTPMFOLLOA-UHFFFAOYSA-N 1-chloro-2-ethoxyethane Chemical compound CCOCCCl GPTVQTPMFOLLOA-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-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
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
IVUAAOBNUNMJQC-UHFFFAOYSA-N 5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC=CC=C2NC(=O)CN=C1C1=CC=CC=C1 IVUAAOBNUNMJQC-UHFFFAOYSA-N 0.000 description 1
JAJMDCWDIQLCTN-UHFFFAOYSA-N 7-chloro-1-(2-morpholin-4-ylethyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound O=C1CN=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2N1CCN1CCOCC1 JAJMDCWDIQLCTN-UHFFFAOYSA-N 0.000 description 1
QHNWTXJHPWAPMS-UHFFFAOYSA-N 7-chloro-1-[2-(diethylamino)ethyl]-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCN(CC)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 QHNWTXJHPWAPMS-UHFFFAOYSA-N 0.000 description 1
KEHBRAFAGBILBF-UHFFFAOYSA-N 7-chloro-1-[2-(dimethylamino)ethyl]-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCN(C)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 KEHBRAFAGBILBF-UHFFFAOYSA-N 0.000 description 1
NUYBDBWVWLROHV-UHFFFAOYSA-N 7-chloro-1-[3-(dimethylamino)propyl]-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCN(C)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 NUYBDBWVWLROHV-UHFFFAOYSA-N 0.000 description 1
HCGXHCQLJCFGAB-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-1-(3-piperazin-1-ylpropyl)-3h-1,4-benzodiazepin-2-one Chemical compound FC1=CC=CC=C1C(C1=CC(Cl)=CC=C11)=NCC(=O)N1CCCN1CCNCC1 HCGXHCQLJCFGAB-UHFFFAOYSA-N 0.000 description 1
BLCXTJIOJVGBHB-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-1-(3-piperazin-1-ylpropyl)-3h-1,4-benzodiazepin-2-one;hydrochloride Chemical compound Cl.FC1=CC=CC=C1C(C1=CC(Cl)=CC=C11)=NCC(=O)N1CCCN1CCNCC1 BLCXTJIOJVGBHB-UHFFFAOYSA-N 0.000 description 1
MVNSMCNZEKGRQF-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-1-[2-(4-methylpiperazin-1-yl)ethyl]-3h-1,4-benzodiazepin-2-one;trihydrochloride Chemical compound Cl.Cl.Cl.C1CN(C)CCN1CCN1C(=O)CN=C(C=2C(=CC=CC=2)F)C2=CC(Cl)=CC=C21 MVNSMCNZEKGRQF-UHFFFAOYSA-N 0.000 description 1
NLHXADRVQRKKHG-UHFFFAOYSA-N 7-chloro-5-phenyl-1-(2-piperidin-1-ylethyl)-3h-1,4-benzodiazepin-2-one Chemical compound O=C1CN=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2N1CCN1CCCCC1 NLHXADRVQRKKHG-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000003302 alkenyloxy group Chemical group 0.000 description 1
125000005452 alkenyloxyalkyl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000002585 base Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000009089 cytolysis Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
UVCOILFBWYKHHB-UHFFFAOYSA-N desalkylflurazepam Chemical compound FC1=CC=CC=C1C1=NCC(=O)NC2=CC=C(Cl)C=C12 UVCOILFBWYKHHB-UHFFFAOYSA-N 0.000 description 1
PSUPORXCGKAVFW-UHFFFAOYSA-N dimethyl-[2-[2-oxo-5-phenyl-7-(trifluoromethyl)-3,4-dihydro-1,4-benzodiazepin-1-ium-1-yl]ethyl]azanium;dichloride Chemical compound [Cl-].[Cl-].N1CC(=O)[N+](CC[NH+](C)C)=C2C=CC(C(F)(F)F)=CC2=C1C1=CC=CC=C1 PSUPORXCGKAVFW-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
SAADBVWGJQAEFS-UHFFFAOYSA-N flurazepam Chemical compound N=1CC(=O)N(CCN(CC)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F SAADBVWGJQAEFS-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
229940013688 formic acid Drugs 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
239000011630 iodine 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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940098895 maleic acid Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
AKPLHCDWDRPJGD-UHFFFAOYSA-N nordazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 AKPLHCDWDRPJGD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
ZLMJMSJWJFRBEC-OUBTZVSYSA-N potassium-40 Chemical compound [40K] ZLMJMSJWJFRBEC-OUBTZVSYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000011121 sodium hydroxide Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 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
230000007306 turnover Effects 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients

Landscapes

Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)

NO152064A 1963-02-19 1964-02-18 NO118706B (pt)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US25975363A	1963-02-19	1963-02-19

Publications (1)

Publication Number	Publication Date
NO118706B true NO118706B (pt)	1970-02-02

Family

ID=22986219

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO152064A NO118706B (pt)	1963-02-19	1964-02-18

Country Status (12)

Country	Link
BE (1)	BE643885A (pt)
BR (1)	BR6456904D0 (pt)
CH (1)	CH449031A (pt)
DE (1)	DE1445888A1 (pt)
DK (1)	DK111004B (pt)
ES (1)	ES296566A1 (pt)
FR (2)	FR3253M (pt)
GB (1)	GB1050401A (pt)
NL (1)	NL142958B (pt)
NO (1)	NO118706B (pt)
OA (1)	OA02392A (pt)
SE (2)	SE319483B (pt)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT361492B (de) *	1978-12-18	1981-03-10	Gerot Pharmazeutika	Verfahren zur herstellung von neuen 3-hydroxy- 1,4-benzodiazepin-2-onen

0
- GB GB1050401D patent/GB1050401A/en not_active Expired
1964
- 1964-01-31 CH CH114264A patent/CH449031A/de unknown
- 1964-02-04 DE DE19641445888 patent/DE1445888A1/de active Pending
- 1964-02-14 NL NL646401335A patent/NL142958B/xx not_active IP Right Cessation
- 1964-02-17 BE BE643885D patent/BE643885A/xx unknown
- 1964-02-17 FR FR963972A patent/FR3253M/fr active Active
- 1964-02-17 FR FR963971A patent/FR1388222A/fr not_active Expired
- 1964-02-18 BR BR15690464A patent/BR6456904D0/pt unknown
- 1964-02-18 ES ES296566A patent/ES296566A1/es not_active Expired
- 1964-02-18 NO NO152064A patent/NO118706B/no unknown
- 1964-02-19 DK DK80564A patent/DK111004B/da unknown
- 1964-02-19 SE SE200264A patent/SE319483B/xx unknown
1966
- 1966-02-21 SE SE222966A patent/SE319773B/xx unknown
1967
- 1967-03-30 OA OA52857A patent/OA02392A/xx unknown

Also Published As

Publication number	Publication date
GB1050401A (pt)	1900-01-01
CH449031A (de)	1967-12-31
BR6456904D0 (pt)	1973-08-09
NL142958B (nl)	1974-08-15
SE319773B (pt)	1970-01-26
FR1388222A (fr)	1965-02-05
BE643885A (pt)	1964-08-17
SE319483B (pt)	1970-01-19
NL6401335A (pt)	1964-08-20
FR3253M (pt)	1965-04-20
ES296566A1 (es)	1964-08-16
DK111004B (da)	1968-04-29
DE1445888A1 (de)	1968-12-19
OA02392A (fr)	1970-05-05

Publication	Publication Date	Title
US3551428A (en)	1970-12-29	New 1- (or 2-) substituted 4-mercapto-pyrazolo(3,4-d)pyrimidines
NO152064B (no)	1985-04-15	Utvidet stiveranordning for en selvreisende vinge
DE2203782A1 (de)	1972-08-24	Verfahren zur Herstellung von Triazolobenzodiazepinen sowie neue Triazolobenzodiazepine und deren Zwischenprodukte
NO126734B (pt)	1973-03-19
US4013665A (en)	1977-03-22	Antiviral, substituted 1,3-dimethyl-1h-pyrazolo(3,4b)quinolines
NO802326L (no)	1981-02-04	Fremgangsmaate ved fremstilling av substituerte tetraazatricyklen
DE2424334A1 (de)	1974-12-19	Verfahren zur herstellung neuer heterocyclischer verbindungen
NO122124B (pt)	1971-05-24
FI61309C (fi)	1982-07-12	Foerfarande foer framstaellning av nya psykosedativa och antikonvulsiva 5-fenyl-1h-1,5-benzodiazepin-2,4-dioner
CS255897B2 (en)	1988-03-15	Process for preparing 1,2,4-triazolocarbamates
US3399196A (en)	1968-08-27	Nu-substituted pyrazolo-pyrimidines
NO118706B (pt)	1970-02-02
NO158185B (no)	1988-04-18	Analogifremgangsmaate ved fremstilling av terapeutisk aktive 1,5-difenylpyrazolin-3-on-forbindelser.
DE2215943A1 (de)	1972-10-12	Neue 6-Phenyl-4H-s-triazolo eckige Klammer auf 1,5-a eckige Klammer zu eckige Klammer auf 1,4 eckige Klammer zu benzodiazepin-2-carbonsäuren und ihre Ester, sowie Verfahren zu deren Herstellung
US3184460A (en)	1965-05-18	1-(alkoxyphenylalkyl)-2-imidazolinones, -2-imidazolidinones and -2-pyrimidinones
NO119593B (pt)	1970-06-08
US3446806A (en)	1969-05-27	Process for the preparation of 1,4-benzodiazepine 4-oxides
IL32604A (en)	1972-10-29	5-Aryl Compounds-H1-1,5-Benzodiazepine-2,4-Discussion and Preparation
US3200120A (en)	1965-08-10	Hydrazides of 4-substituted 1-aminopiperazines
DK155883B (da)	1989-05-29	Analogifremgangsmaade til fremstilling af triazoloquinazolinonderivater
FI79847C (fi)	1990-03-12	Foerfarande foer framstaellning av terapeutiskt anvaendbara akridanon-derivat.
US4002638A (en)	1977-01-11	Benzazepine derivatives
US3336303A (en)	1967-08-15	Dibenzo-azacycloalkane-n-carboxylic acid hydrazides
US3933805A (en)	1976-01-20	S(IV)-benzo-1,2,4-thiadiazine compounds and process for their preparation
NO129744B (pt)	1974-05-20