CH499486A - Verfahren zur Herstellung von 10-Aminoalkyl-9,10-dihydroanthracenverbindungen - Google Patents

Verfahren zur Herstellung von 10-Aminoalkyl-9,10-dihydroanthracenverbindungen

Info

Publication number: CH499486A
Authority: CH; Switzerland
Prior art keywords: acid; dihydroanthracene; lower alkyl; group; ether
Prior art date: 1966-02-14

Application number

CH160667A

Other languages

German (de)

English (en)

Inventor

Norman Craig Paul

Leon Zirkle Charles

Original Assignee

Smith Kline French Lab

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.)

1966-02-14

Filing date

1967-02-03

Publication date

1970-11-30

1967-02-03 Application filed by Smith Kline French Lab filed Critical Smith Kline French Lab

1970-11-30 Publication of CH499486A publication Critical patent/CH499486A/de

Links

125000000217 alkyl group Chemical group 0.000 claims abstract description 18
150000003839 salts Chemical class 0.000 claims abstract description 10
229910052801 chlorine Inorganic materials 0.000 claims abstract description 6
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
-1 N, N-dimethylsulfamyl group Chemical group 0.000 claims description 33
150000001875 compounds Chemical class 0.000 claims description 32
238000000034 method Methods 0.000 claims description 19
230000008569 process Effects 0.000 claims description 13
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 8
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
150000007522 mineralic acids Chemical class 0.000 claims description 4
150000007524 organic acids Chemical class 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
229910000043 hydrogen iodide Inorganic materials 0.000 claims description 3
229910052698 phosphorus Inorganic materials 0.000 claims description 3
239000011574 phosphorus Substances 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
229910021529 ammonia Inorganic materials 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000005265 dialkylamine group Chemical group 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
150000001412 amines Chemical class 0.000 claims 1
230000001419 dependent effect Effects 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 8
229910052794 bromium Inorganic materials 0.000 abstract description 3
229910052757 nitrogen Inorganic materials 0.000 abstract description 2
125000003282 alkyl amino group Chemical group 0.000 abstract 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
239000000935 antidepressant agent Chemical group 0.000 abstract 1
229940005513 antidepressants Drugs 0.000 abstract 1
125000005842 heteroatom Chemical group 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 76
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 25
239000000243 solution Substances 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000012259 ether extract Substances 0.000 description 9
239000000155 melt Substances 0.000 description 9
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 7
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 6
239000011777 magnesium Substances 0.000 description 6
229910052749 magnesium Inorganic materials 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 4
XCGWCDYXZKWUTI-UHFFFAOYSA-N 10-(3-bromopropyl)-2-(trifluoromethyl)anthracene Chemical compound FC(C1=CC2=CC3=CC=CC=C3C(=C2C=C1)CCCBr)(F)F XCGWCDYXZKWUTI-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
CYXGMKKEOBFWHT-UHFFFAOYSA-N [2-bromo-4-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound BrC1=C(C(=O)C2=CC=CC=C2)C=CC(=C1)C(F)(F)F CYXGMKKEOBFWHT-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
239000002585 base Substances 0.000 description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
239000000284 extract Substances 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
BQLHMMQUVJCTAN-UHFFFAOYSA-N 1-chloro-3-methoxypropane Chemical compound COCCCCl BQLHMMQUVJCTAN-UHFFFAOYSA-N 0.000 description 3
UXZRVSUQEAZSQJ-UHFFFAOYSA-N 3-(trifluoromethyl)-10H-anthracen-9-one Chemical compound FC(C1=CC=2CC3=CC=CC=C3C(C2C=C1)=O)(F)F UXZRVSUQEAZSQJ-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 3
239000012458 free base Substances 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
239000000725 suspension Substances 0.000 description 3
JAARPJXCACBYQW-UHFFFAOYSA-N 2-(1-phenylethyl)-5-(trifluoromethyl)benzonitrile Chemical compound CC(C1=CC=CC=C1)C1=C(C=C(C=C1)C(F)(F)F)C#N JAARPJXCACBYQW-UHFFFAOYSA-N 0.000 description 2
LNUBRODMYSPWRH-UHFFFAOYSA-N 2-[2-bromo-4-(trifluoromethyl)phenyl]-2-phenyloxirane Chemical compound C1(=CC=CC=C1)C1(CO1)C1=C(C=C(C=C1)C(F)(F)F)Br LNUBRODMYSPWRH-UHFFFAOYSA-N 0.000 description 2
FPCCZJVGSRIMLO-UHFFFAOYSA-N 2-benzyl-5-(trifluoromethyl)benzoic acid Chemical compound C(C1=CC=CC=C1)C1=C(C(=O)O)C=C(C=C1)C(F)(F)F FPCCZJVGSRIMLO-UHFFFAOYSA-N 0.000 description 2
YQDJZASWOJHHGY-UHFFFAOYSA-N 2-bromo-4-(trifluoromethyl)benzonitrile Chemical compound FC(F)(F)C1=CC=C(C#N)C(Br)=C1 YQDJZASWOJHHGY-UHFFFAOYSA-N 0.000 description 2
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-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
239000005711 Benzoic acid Substances 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
GGXIUDGQCDFBLW-UHFFFAOYSA-N N,N-dimethyl-3-[3-(trifluoromethyl)-9,10-dihydroanthracen-9-yl]propan-1-amine Chemical compound CN(CCCC1C=2C=CC(=CC2CC2=CC=CC=C12)C(F)(F)F)C GGXIUDGQCDFBLW-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
150000008425 anthrones Chemical class 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
229910002092 carbon dioxide Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
230000014509 gene expression Effects 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000002466 imines Chemical class 0.000 description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
229960004889 salicylic acid Drugs 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
BPLKQGGAXWRFOE-UHFFFAOYSA-M trimethylsulfoxonium iodide Chemical compound [I-].C[S+](C)(C)=O BPLKQGGAXWRFOE-UHFFFAOYSA-M 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VRMVEKQFSYMWBK-UHFFFAOYSA-N 1-[2-bromo-4-(trifluoromethyl)phenyl]-1-phenylethanol Chemical compound C1(=CC=CC=C1)C(C)(O)C1=C(C=C(C=C1)C(F)(F)F)Br VRMVEKQFSYMWBK-UHFFFAOYSA-N 0.000 description 1
VUCHWIWJCNBSQS-UHFFFAOYSA-N 1-chloro-3-methoxy-2-methylpropane Chemical compound COCC(C)CCl VUCHWIWJCNBSQS-UHFFFAOYSA-N 0.000 description 1
ZUKRNCHBKRLOTF-UHFFFAOYSA-N 1-methyl-9,10-dihydroanthracene Chemical compound C1C2=CC=CC=C2CC2=C1C=CC=C2C ZUKRNCHBKRLOTF-UHFFFAOYSA-N 0.000 description 1
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
VGCBJVPJSOELMP-UHFFFAOYSA-N 2-benzyl-5-(trifluoromethyl)benzonitrile Chemical compound C(C1=CC=CC=C1)C1=C(C#N)C=C(C=C1)C(F)(F)F VGCBJVPJSOELMP-UHFFFAOYSA-N 0.000 description 1
LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
IFRKEAUJMRIYNC-UHFFFAOYSA-N 2-piperazin-1-ylethyl acetate Chemical compound CC(=O)OCCN1CCNCC1 IFRKEAUJMRIYNC-UHFFFAOYSA-N 0.000 description 1
MVPQIDZRNBWJEX-UHFFFAOYSA-N 3-chloro-10h-anthracen-9-one Chemical compound C1=CC=C2CC3=CC(Cl)=CC=C3C(=O)C2=C1 MVPQIDZRNBWJEX-UHFFFAOYSA-N 0.000 description 1
DSOBIPNVGFJEJJ-UHFFFAOYSA-N 3-methyl-10h-anthracen-9-one Chemical compound C1=CC=C2CC3=CC(C)=CC=C3C(=O)C2=C1 DSOBIPNVGFJEJJ-UHFFFAOYSA-N 0.000 description 1
YXCSUTHITHXTHZ-UHFFFAOYSA-N 4-methyl-10h-anthracen-9-one Chemical compound O=C1C2=CC=CC=C2CC2=C1C=CC=C2C YXCSUTHITHXTHZ-UHFFFAOYSA-N 0.000 description 1
SKTFQHRVFFOHTQ-UHFFFAOYSA-N 8-bromo-1,3-dimethyl-7h-purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC(Br)=N2 SKTFQHRVFFOHTQ-UHFFFAOYSA-N 0.000 description 1
YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
WPDAVTSOEQEGMS-UHFFFAOYSA-N 9,10-dihydroanthracene Chemical compound C1=CC=C2CC3=CC=CC=C3CC2=C1 WPDAVTSOEQEGMS-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-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
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
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 1
229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
SOXIECQAWOVRDT-UHFFFAOYSA-N N,N-dimethyl-3-[10-methyl-3-(trifluoromethyl)-9,10-dihydroanthracen-9-yl]propan-1-amine Chemical compound FC(C1=CC=2C(C3=CC=CC=C3C(C2C=C1)CCCN(C)C)C)(F)F SOXIECQAWOVRDT-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 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
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229960004050 aminobenzoic acid Drugs 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
150000001454 anthracenes Chemical class 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
150000008359 benzonitriles Chemical class 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-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
210000003169 central nervous system Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000008570 general process Effects 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
229960002989 glutamic acid Drugs 0.000 description 1
229960004275 glycolic acid Drugs 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
125000006178 methyl benzyl group Chemical group 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
230000003287 optical 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
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
QARVLSVVCXYDNA-UHFFFAOYSA-N phenyl bromide Natural products BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000003385 ring cleavage reaction Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 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
- C07D295/06—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 halogen atoms or nitro radicals

Landscapes

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

CH160667A 1966-02-14 1967-02-03 Verfahren zur Herstellung von 10-Aminoalkyl-9,10-dihydroanthracenverbindungen CH499486A (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US52697566A	1966-02-14	1966-02-14

Publications (1)

Publication Number	Publication Date
CH499486A true CH499486A (de)	1970-11-30

Family

ID=24099585

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH160667A CH499486A (de)	1966-02-14	1967-02-03	Verfahren zur Herstellung von 10-Aminoalkyl-9,10-dihydroanthracenverbindungen

Country Status (11)

Country	Link
BE (1)	BE694036A (it)
CH (1)	CH499486A (it)
DE (1)	DE1618850C3 (it)
DK (1)	DK134514B (it)
ES (1)	ES336734A1 (it)
FR (1)	FR6180M (it)
GB (2)	GB1160218A (it)
IL (1)	IL27389A (it)
IT (1)	IT1033005B (it)
NL (1)	NL153853B (it)
SE (1)	SE309037B (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3694514A (en) *	1971-03-05	1972-09-26	Smith Kline French Lab	10-bromoalkyl-anthracenes

1967
- 1967-02-03 CH CH160667A patent/CH499486A/de not_active IP Right Cessation
- 1967-02-05 IL IL2738967A patent/IL27389A/xx unknown
- 1967-02-08 DE DE1967S0108223 patent/DE1618850C3/de not_active Expired
- 1967-02-08 GB GB299169A patent/GB1160218A/en not_active Expired
- 1967-02-08 GB GB611667A patent/GB1160217A/en not_active Expired
- 1967-02-09 IT IT1247067A patent/IT1033005B/it active
- 1967-02-11 ES ES336734A patent/ES336734A1/es not_active Expired
- 1967-02-13 SE SE198267A patent/SE309037B/xx unknown
- 1967-02-14 BE BE694036D patent/BE694036A/xx not_active IP Right Cessation
- 1967-02-14 DK DK81167A patent/DK134514B/da not_active IP Right Cessation
- 1967-02-14 FR FR94795A patent/FR6180M/fr not_active Expired
- 1967-02-14 NL NL6702224A patent/NL153853B/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
IT1033005B (it)	1979-07-10
DE1618850C3 (de)	1980-10-30
FR6180M (it)	1968-07-15
DK134514C (it)	1977-04-18
DK134514B (da)	1976-11-22
DE1618850A1 (de)	1971-07-22
GB1160217A (en)	1969-08-06
ES336734A1 (es)	1968-01-01
NL153853B (nl)	1977-07-15
IL27389A (en)	1971-11-29
SE309037B (it)	1969-03-10
GB1160218A (en)	1969-08-06
BE694036A (fr)	1967-08-14
DE1618850B2 (de)	1980-02-21
NL6702224A (it)	1967-08-15

Legal Events

Date	Code	Title	Description
1982-11-15	PFA	Name/firm changed	Owner name: SMITHKLINE CORPORATION DANN IN SMITHKLINE BECKMA
1987-04-30	PL	Patent ceased

Publication	Publication Date	Title
DE1138779B (de)	1962-10-31	Verfahren zur Herstellung von in der Aminogruppe substituierten 10-(Aminoalkyl)-trifluormethyl-phenthiazinderivaten.
DE1958919B2 (de)	1979-10-18	l-Oxo-5-indanyloxyessigsäuren und solche Verbindungen enthaltende Arzneimittel
DD156369A5 (de)	1982-08-18	Herstellung von rechtsdrehenden 5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3b]-indolen
DE2505239A1 (de)	1975-08-14	Verfahren zur herstellung tetracyclischer verbindungen
DE2812578A1 (de)	1978-10-05	1-aminoindane und verfahren zu ihrer herstellung
DE1037461B (de)	1958-08-28	Verfahren zur Herstellung von Phenthiazinderivaten
DE2607305C2 (de)	1987-04-30	6-Oxo-6H-indeno[5,4-b]furan-2-carbonsäuren, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2412522A1 (de)	1974-10-10	Tricyclische verbindungen
CH499486A (de)	1970-11-30	Verfahren zur Herstellung von 10-Aminoalkyl-9,10-dihydroanthracenverbindungen
CH631969A5 (de)	1982-09-15	Verfahren zur herstellung von aminen.
CH619683A5 (it)	1980-10-15
DE2609015A1 (de)	1976-09-16	Verfahren zur herstellung von benz (f)-2,5-oxazocinen
DE1921842A1 (de)	1969-11-20	Verfahren zur Herstellung von cycloaliphatischen Halogeniden
DE1695962A1 (de)	1971-05-19	(2-Aminocycloalkyl)hydrochinone und Derivate derselben sowie Verfahren zu ihrer Herstellung
DE2121996C3 (de)	1982-04-01	Dibasische Äther des 2,6- und 2,7-Dihydroxyanthrachinons der Herstellung und pharmazeutische Zubereitung
DE1695963A1 (de)	1971-05-19	Cycloalkenamin-p-benzochinonaddukte und Verfahren zu ihrer Herstellung
DE2742174A1 (de)	1979-03-29	Verfahren zur herstellung von aminen
AT210428B (de)	1960-08-10	Verfahren zur Herstellung von neuen, mit einer einwertigen Schwefelfunktion substituierten Pyrido-benzthiazin-Derivaten
DE2120996C3 (de)	1980-04-17	Bis-basische Ketone des Dibenzothiophens, Verfahren zu deren Herstellung und ihre Verwendung bei der Bekämpfung von Virusinfektionen
AT269154B (de)	1969-03-10	Verfahren zur Herstellung von neuen 10-Aminoalkyl-11-oxo-10,11-dihydro-dibenzo[b,f][1,4]oxazepinen und deren Salzen
DE2124403A1 (de)	1972-11-30	Verfahren zur Herstellung von Amitnptyhn und verwandten Verbindungen
DE2356358C2 (de)	1984-12-06	Verfahren zur Bromierung von Pyrimidin-hydrochlorid oder -hydrobromid
DE2116548C3 (de)	1974-07-04	Verfahren zur Herstellung von 2,6-Dicyan-trichlorpyridin
AT228194B (de)	1963-07-10	Verfahren zur Herstellung von neuen 2-Aryl-2-aminoalkylmercaptoäthansäureamiden, sowie ihren Säureadditionssalzen, quärtaren Salzen und S-Oxyden
CH593970A5 (en)	1977-12-30	10-(4-Substd. piperazino) dibenzo (b,f) thiepins - CNS depressants without cataleptic side-effects