NO119593B - - Google Patents

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Publication number: NO119593B
Authority: NO; Norway
Prior art keywords: formula; lower alkyl; group; compound; benzophenone
Prior art date: 1965-09-22

Application number

NO164845A

Other languages

English (en)

Norwegian (no)

Inventor

L Sternbach

R Fryer

E Reeder

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.)

1965-09-22

Filing date

1966-09-22

Publication date

1970-06-08

1966-09-22 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1970-06-08 Publication of NO119593B publication Critical patent/NO119593B/no

Links

150000001875 compounds Chemical class 0.000 claims description 55
125000000217 alkyl group Chemical group 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 13
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
239000012965 benzophenone Substances 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 8
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 8
239000000047 product Substances 0.000 claims description 7
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
229910021529 ammonia Inorganic materials 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
HKNSIVFWRXBWCK-UHFFFAOYSA-N [N].NC1=CC=CC=C1 Chemical group [N].NC1=CC=CC=C1 HKNSIVFWRXBWCK-UHFFFAOYSA-N 0.000 claims description 4
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
FHBXQJDYHHJCIF-UHFFFAOYSA-N (2,3-diaminophenyl)-phenylmethanone Chemical class NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N FHBXQJDYHHJCIF-UHFFFAOYSA-N 0.000 claims description 3
238000005804 alkylation reaction Methods 0.000 claims description 3
239000007795 chemical reaction product Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
150000003973 alkyl amines Chemical class 0.000 claims 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
239000000203 mixture Substances 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
239000003921 oil Substances 0.000 description 12
235000019198 oils Nutrition 0.000 description 12
238000001953 recrystallisation Methods 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
-1 methoxy, ethoxy, isopropyloxy Chemical group 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
150000003141 primary amines Chemical class 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
229940024874 benzophenone Drugs 0.000 description 5
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 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000010410 layer Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
BVLQQZBPPMLLAY-UHFFFAOYSA-N [5-chloro-2-(3-chloropropylamino)phenyl]-phenylmethanone Chemical compound ClCCCNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 BVLQQZBPPMLLAY-UHFFFAOYSA-N 0.000 description 3
230000037396 body weight Effects 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
210000003169 central nervous system Anatomy 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
GTNGBHWYALUTBM-UHFFFAOYSA-N diphenylmethanone;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(=O)C1=CC=CC=C1 GTNGBHWYALUTBM-UHFFFAOYSA-N 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000000155 melt Substances 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-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
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
WNLLCLUIZQVOTO-UHFFFAOYSA-N [5-chloro-2-[3-(dimethylamino)propylamino]phenyl]-phenylmethanone Chemical compound CN(C)CCCNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WNLLCLUIZQVOTO-UHFFFAOYSA-N 0.000 description 2
ZKESTXHTKQWPHZ-UHFFFAOYSA-N [5-chloro-2-[3-(dimethylamino)propylamino]phenyl]-phenylmethanone hydrochloride Chemical compound Cl.ClC=1C=CC(=C(C(=O)C2=CC=CC=C2)C1)NCCCN(C)C ZKESTXHTKQWPHZ-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
150000008366 benzophenones Chemical class 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
239000011630 iodine Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
229930195734 saturated hydrocarbon Natural products 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
150000003385 sodium Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
QFUBTOHBIMBMQF-UHFFFAOYSA-N (1-fluorocyclohexa-2,4-dien-1-yl)-phenylmethanone Chemical compound FC1(C(=O)C2=CC=CC=C2)CC=CC=C1 QFUBTOHBIMBMQF-UHFFFAOYSA-N 0.000 description 1
HRPHZUAPQWJPCZ-UHFFFAOYSA-N (2-chloro-5-nitrophenyl)-phenylmethanone Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C(=O)C=2C=CC=CC=2)=C1 HRPHZUAPQWJPCZ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-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
NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
KWVSVDJFPBRMHC-UHFFFAOYSA-N CN(C)CCCN(C1=C(C=C(Cl)C=C1)C(=O)C1=CC=CC=C1)S(=O)(=O)C1=CC=C(C)C=C1 Chemical compound CN(C)CCCN(C1=C(C=C(Cl)C=C1)C(=O)C1=CC=CC=C1)S(=O)(=O)C1=CC=C(C)C=C1 KWVSVDJFPBRMHC-UHFFFAOYSA-N 0.000 description 1
PSPZRKYTCZLWGN-UHFFFAOYSA-N Cl.NCCCNC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)Cl Chemical compound Cl.NCCCNC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)Cl PSPZRKYTCZLWGN-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
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
229920002472 Starch Polymers 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
JBWDODLNADCAPN-UHFFFAOYSA-N [2-(3-aminopropylamino)-5-chlorophenyl]-phenylmethanone Chemical compound NCCCNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 JBWDODLNADCAPN-UHFFFAOYSA-N 0.000 description 1
HNKXCJXKXCSLAK-UHFFFAOYSA-N [2-(3-aminopropylamino)-5-nitrophenyl]-phenylmethanone Chemical compound NCCCNC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)[N+](=O)[O-] HNKXCJXKXCSLAK-UHFFFAOYSA-N 0.000 description 1
JVOSCQBSMBONFO-UHFFFAOYSA-N [2-(3-aminopropylamino)-5-nitrophenyl]-phenylmethanone hydrochloride Chemical compound Cl.NCCCNC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)[N+](=O)[O-] JVOSCQBSMBONFO-UHFFFAOYSA-N 0.000 description 1
RWWODOMYDKTRCF-UHFFFAOYSA-N [2-[3-(dimethylamino)propylamino]-5-nitrophenyl]-phenylmethanone Chemical compound CN(CCCNC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)[N+](=O)[O-])C RWWODOMYDKTRCF-UHFFFAOYSA-N 0.000 description 1
VVUUZVWYATYYGT-UHFFFAOYSA-N [2-[3-(dimethylamino)propylamino]-5-nitrophenyl]-phenylmethanone hydrochloride Chemical compound Cl.CN(CCCNC1=C(C(=O)C2=CC=CC=C2)C=C(C=C1)[N+](=O)[O-])C VVUUZVWYATYYGT-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
230000001430 anti-depressive effect Effects 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000000872 buffer Substances 0.000 description 1
RGTXVXDNHPWPHH-UHFFFAOYSA-N butane-1,3-diamine Chemical compound CC(N)CCN RGTXVXDNHPWPHH-UHFFFAOYSA-N 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
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
210000003746 feather Anatomy 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000003278 haem Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
235000013847 iso-butane Nutrition 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
WZTIKNRSYKDRQF-UHFFFAOYSA-N n-(2-benzoyl-4-chlorophenyl)-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WZTIKNRSYKDRQF-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 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
239000012074 organic phase Substances 0.000 description 1
230000003204 osmotic effect Effects 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
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000005060 rubber Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
125000004436 sodium atom Chemical group 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
229960005333 tetrabenazine Drugs 0.000 description 1
NNPPMTNAJDCUHE-UHFFFAOYSA-N trimethylmethane Natural products CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/53—Nitrogen atoms
- 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
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO164845A 1965-09-22 1966-09-22 NO119593B (pt)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US48938165A	1965-09-22	1965-09-22
US75868368A	1968-09-10	1968-09-10

Publications (1)

Publication Number	Publication Date
NO119593B true NO119593B (pt)	1970-06-08

Family

ID=27049698

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO164845A NO119593B (pt)	1965-09-22	1966-09-22

Country Status (12)

Country	Link
US (2)	US3431304A (pt)
BE (3)	BE686909A (pt)
BR (3)	BR6683054D0 (pt)
CH (2)	CH525862A (pt)
DE (2)	DE1543666A1 (pt)
DK (1)	DK129924B (pt)
FI (1)	FI46154C (pt)
FR (5)	FR6162M (pt)
IL (1)	IL26508A (pt)
NL (3)	NL6613323A (pt)
NO (1)	NO119593B (pt)
SE (1)	SE344064B (pt)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4155934A (en) *	1965-12-03	1979-05-22	L'oreal	Hair dye compounds
US3904690A (en) *	1965-12-03	1975-09-09	Oreal	2-Nitro-meta-phenylenediamines
GB1274307A (en) *	1968-06-13	1972-05-17	Sumitomo Chemical Co	Process for producing aminobenzophenone derivatives and their salts
US3927010A (en) *	1969-10-17	1975-12-16	Hoffmann La Roche	Diarylmethane derivatives and processes for their preparation
US3904603A (en) *	1974-08-01	1975-09-09	American Home Prod	2,3,4,5-tetrahydro-4,4-dialkyl-1h-1,4-benzodiazepine halides
JPS6019753A (ja) *	1983-07-13	1985-01-31	Shionogi & Co Ltd	オルト−（モノ置換アミノ）フエニルイミン類およびその製造法
US4560510A (en) *	1984-04-06	1985-12-24	A. H. Robins Company, Incorporated	Process and intermediates for the preparation of aryl substituted pyrido[1,4]benzodiazepines

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3141890A (en) *		1964-07-21		Certificate of correction
US3182054A (en) *		1965-05-04		Benzodiazepine - compounds
US3222359A (en) *		1965-12-07		Process for preparing benzodiazepine compounds
US3131178A (en) *		1964-04-28		Process for producing s-phenyl-l
US3136815A (en) *	1959-12-10	1964-06-09	Hoffmann La Roche	Amino substituted benzophenone oximes and derivatives thereof
US3239564A (en) *	1960-12-02	1966-03-08	Reeder Earl	2 n-substituted amino halobenzo-phenones
US3203990A (en) *	1962-03-21	1965-08-31	Hoffmann La Roche	2-amino-2'-halo-5-nitro benzophenones

1965
- 1965-09-22 US US489381A patent/US3431304A/en not_active Expired - Lifetime
1966
- 1966-09-03 DE DE19661543666 patent/DE1543666A1/de active Pending
- 1966-09-09 CH CH1309466A patent/CH525862A/de not_active IP Right Cessation
- 1966-09-09 CH CH1700970A patent/CH537902A/de not_active IP Right Cessation
- 1966-09-12 DE DE19661543668 patent/DE1543668A1/de active Pending
- 1966-09-12 FR FR75966A patent/FR6162M/fr not_active Expired
- 1966-09-14 IL IL26508A patent/IL26508A/xx unknown
- 1966-09-15 BE BE686909D patent/BE686909A/xx unknown
- 1966-09-16 FR FR76762A patent/FR1493255A/fr not_active Expired
- 1966-09-20 BE BE687123D patent/BE687123A/xx unknown
- 1966-09-20 BE BE687122D patent/BE687122A/xx unknown
- 1966-09-21 FI FI662479A patent/FI46154C/fi active
- 1966-09-21 FR FR77059A patent/FR1508140A/fr not_active Expired
- 1966-09-21 NL NL6613323A patent/NL6613323A/xx unknown
- 1966-09-21 BR BR183054/66A patent/BR6683054D0/pt unknown
- 1966-09-21 BR BR183057/66A patent/BR6683057D0/pt unknown
- 1966-09-21 BR BR183056/66A patent/BR6683056D0/pt unknown
- 1966-09-22 NL NL6613405A patent/NL6613405A/xx unknown
- 1966-09-22 NO NO164845A patent/NO119593B/no unknown
- 1966-09-22 FR FR77211A patent/FR1500341A/fr not_active Expired
- 1966-09-22 DK DK492066AA patent/DK129924B/da unknown
- 1966-09-22 SE SE12797/66A patent/SE344064B/xx unknown
- 1966-09-22 NL NL666613406A patent/NL151066B/xx not_active IP Right Cessation
- 1966-10-21 FR FR80921A patent/FR6670M/fr not_active Expired
1968
- 1968-09-10 US US758683A patent/US3562325A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
SE344064B (pt)	1972-03-27
DE1543668A1 (de)	1972-04-13
NL6613406A (pt)	1967-03-23
NL6613323A (pt)	1967-03-23
FI46154C (fi)	1973-01-10
CH537902A (de)	1973-07-31
FR6670M (pt)	1969-02-03
DE1543666A1 (de)	1969-09-11
CH525862A (de)	1972-07-31
NL151066B (nl)	1976-10-15
IL26508A (en)	1971-04-28
DK129924B (da)	1974-12-02
FR1508140A (fr)	1968-01-05
BE687123A (pt)	1967-03-20
FR6162M (pt)	1968-07-08
BR6683054D0 (pt)	1973-12-04
NL6613405A (pt)	1967-03-23
BE687122A (pt)	1967-03-20
US3562325A (en)	1971-02-09
BR6683056D0 (pt)	1973-12-04
DK129924C (pt)	1975-05-12
BE686909A (pt)	1967-03-15
FR1493255A (fr)	1967-08-25
FR1500341A (fr)	1967-11-03
US3431304A (en)	1969-03-04
FI46154B (pt)	1972-10-02
BR6683057D0 (pt)	1973-12-04

Publication	Publication Date	Title
CA2559733C (en)	2014-05-13	Inhibitors of histone deacetylase
CN101440092B (zh)	2010-11-17	2-吲唑-4-氮杂吲哚-5-氨基衍生物及制备和应用
NO145761B (no)	1982-02-15	Benzodiazocinderivater for anvendelse som utgangsmaterialer ved fremstilling av benzodiazepinderivater, og en ny fremgangsmaate for fremstilling av disse benzodiazocinderivater
Heinelt et al.	2004	A convenient method for the synthesis of 2-amino substituted aza-heterocycles from N, N′-disubstituted thioureas using TsCl/NaOH
US4244950A (en)	1981-01-13	Derivatives of 4-amino-3-sulfonamido-pyridine, their preparation and use
DK155367B (da)	1989-04-03	Analogifremgangsmaade til fremstilling af 2-nitroimidazolderivater
NO167947B (no)	1991-09-16	Lagringsanordning for baand- eller plate-registreringsmedier
NO122814B (pt)	1971-08-16
NO162414B (no)	1989-09-18	Fleksibel beholder for transport og lagring av massegods.
NO119593B (pt)	1970-06-08
NO152064B (no)	1985-04-15	Utvidet stiveranordning for en selvreisende vinge
US2940969A (en)	1960-06-14	1-substituted-4-[3-(9-xanthylidene)-propyl] piperazines and 1-substituted-4-[3-(10-thiaxanthylidene) propyl]-piperazines
DK168010B1 (da)	1994-01-17	Tetrahydroisoquinolinforbindelser og farmaceutisk middel indeholdende en saadan forbindelse
US3060177A (en)	1962-10-23	O-(aminoalkyl)oxime derivatives of heterocyclic aldehydes and ketones
Zinnes et al.	1973	1, 2-Benzothiazines. 6. 3-Carbamoyl-4-hydroxy-2H-1, 2-benzothiazine 1, 1-dioxides as antiinflammatory agents
NO164845B (no)	1990-08-13	Fremgangsmaate ved fremstilling av indanylderivater.
NO162907B (no)	1989-11-27	Analogifremgangsmaate for fremstilling av terapeutisk aktive bis-(piperazinyl-resp. homopiperazinyl)-alkaner.
US2987518A (en)	1961-06-06	Certain 1h [4, 5-c]-imidazopyridines
US3963735A (en)	1976-06-15	Acylated 2-aminothiazole derivatives
US3936459A (en)	1976-02-03	1',4'-Dihydro-1-methyl-spiro [piperidine and pyrrolidine-2,3'(2'H)quinoline]-2'-one compounds
DK141287B (da)	1980-02-18	Analogifremgangsmåde til fremstilling af 5-nitro-imidazolcarbamater eller syreadditionssalte deraf.
GB2081261A (en)	1982-02-17	Condensed as-triazine derivatives and process for preparing the same
US3843636A (en)	1974-10-22	1-(5-(p-methoxyphenyl)furfurylidene)amino)hydantoin
US3184452A (en)	1965-05-18	New aminoalkoxy compounds and process for theik manufacture
NO792275L (no)	1980-01-11	Fremgangsmaate for fremstilling av farmakologisk aktive pyrazolo-pyridinderivater