CA1072554A - Naphthyl derivatives - Google Patents
Naphthyl derivativesInfo
- Publication number
- CA1072554A CA1072554A CA244,443A CA244443A CA1072554A CA 1072554 A CA1072554 A CA 1072554A CA 244443 A CA244443 A CA 244443A CA 1072554 A CA1072554 A CA 1072554A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- group
- naphthyl
- compound
- hydrogen atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000001624 naphthyl group Chemical group 0.000 title claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 118
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 48
- -1 trifuor-methyl Chemical group 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 36
- 150000003839 salts Chemical class 0.000 claims abstract description 35
- 239000000460 chlorine Substances 0.000 claims abstract description 24
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 14
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 13
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 12
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 5
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 15
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 11
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 230000018044 dehydration Effects 0.000 claims description 7
- 238000006297 dehydration reaction Methods 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- IJYRGLAZRIFKAK-UHFFFAOYSA-N 2-[(2,2-dimethyl-4-naphthalen-1-yl-3,4-dihydrochromen-7-yl)oxy]-n,n-dimethylethanamine Chemical compound C1=CC=C2C(C3C4=CC=C(C=C4OC(C)(C)C3)OCCN(C)C)=CC=CC2=C1 IJYRGLAZRIFKAK-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- XTIJHEBQQREOMY-UHFFFAOYSA-N 2,2-dimethyl-4-naphthalen-1-yl-3,4-dihydrochromen-7-ol Chemical compound C1=CC=C2C(C3CC(OC4=CC(O)=CC=C43)(C)C)=CC=CC2=C1 XTIJHEBQQREOMY-UHFFFAOYSA-N 0.000 claims description 3
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 2
- 125000006277 halobenzyl group Chemical group 0.000 claims description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims 21
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 8
- 239000000126 substance Substances 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 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 claims 3
- 125000004429 atom Chemical group 0.000 claims 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- LIWXWAPEGWTNCW-UHFFFAOYSA-N 2-(2,2-dimethyl-4-naphthalen-2-ylchromen-7-yl)oxy-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(C=3C4=CC=C(C=C4OC(C)(C)C=3)OCCN(C)C)=CC=C21 LIWXWAPEGWTNCW-UHFFFAOYSA-N 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000011630 iodine Chemical group 0.000 claims 1
- 229910052740 iodine Chemical group 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- 230000000051 modifying effect Effects 0.000 abstract description 4
- 230000036651 mood Effects 0.000 abstract description 4
- 230000036528 appetite Effects 0.000 abstract description 3
- 235000019789 appetite Nutrition 0.000 abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 208000005156 Dehydration Diseases 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- 229960000443 hydrochloric acid Drugs 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- OQAJORFLUPFRMW-UHFFFAOYSA-N 2,2-dimethyl-4-naphthalen-2-ylchromen-7-ol Chemical compound C1=CC=CC2=CC(C=3C4=CC=C(O)C=C4OC(C=3)(C)C)=CC=C21 OQAJORFLUPFRMW-UHFFFAOYSA-N 0.000 description 3
- NGKCSXNZJUEQSR-UHFFFAOYSA-N 7-hydroxy-4-naphthalen-2-ylchromen-2-one Chemical compound C1=CC=CC2=CC(C=3C4=CC=C(C=C4OC(=O)C=3)O)=CC=C21 NGKCSXNZJUEQSR-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 230000029936 alkylation Effects 0.000 description 3
- 238000005804 alkylation reaction Methods 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 150000008371 chromenes Chemical class 0.000 description 3
- 206010061428 decreased appetite Diseases 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- BXWPGZLRGRRMPR-UHFFFAOYSA-N ethyl 3-(6-methoxynaphthalen-2-yl)-3-oxopropanoate Chemical compound C1=C(OC)C=CC2=CC(C(=O)CC(=O)OCC)=CC=C21 BXWPGZLRGRRMPR-UHFFFAOYSA-N 0.000 description 3
- 229940093499 ethyl acetate Drugs 0.000 description 3
- 235000019439 ethyl acetate Nutrition 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
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- YUOJPDPMLJHIOO-UHFFFAOYSA-N 2-(2,2-dimethyl-4-naphthalen-2-ylchromen-7-yl)oxy-n,n-diethylethanamine Chemical compound C1=CC=CC2=CC(C=3C4=CC=C(C=C4OC(C)(C)C=3)OCCN(CC)CC)=CC=C21 YUOJPDPMLJHIOO-UHFFFAOYSA-N 0.000 description 2
- GBHDDTWINVAOSR-UHFFFAOYSA-N 7-[2-(dimethylamino)ethoxy]-2,2-dimethyl-3h-chromen-4-one Chemical compound O=C1CC(C)(C)OC2=CC(OCCN(C)C)=CC=C21 GBHDDTWINVAOSR-UHFFFAOYSA-N 0.000 description 2
- ZMYVMHIXLOLYNY-UHFFFAOYSA-N 7-hydroxy-4-naphthalen-1-yl-3,4-dihydrochromen-2-one Chemical compound C1=CC=C2C(C3C4=CC=C(C=C4OC(=O)C3)O)=CC=CC2=C1 ZMYVMHIXLOLYNY-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 208000022531 anorexia Diseases 0.000 description 2
- 230000002891 anorexigenic effect Effects 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- 239000000935 antidepressant agent Substances 0.000 description 2
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 2
- 229960000956 coumarin Drugs 0.000 description 2
- 235000001671 coumarin Nutrition 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000007892 solid unit dosage form Substances 0.000 description 2
- WPXMLUUYWNHQOR-CMDGGOBGSA-N (e)-3-naphthalen-1-ylprop-2-enoic acid Chemical compound C1=CC=C2C(/C=C/C(=O)O)=CC=CC2=C1 WPXMLUUYWNHQOR-CMDGGOBGSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GGWCZBGAIGGTDA-UHFFFAOYSA-N 1-(6-methoxynaphthalen-2-yl)ethanone Chemical compound C1=C(C(C)=O)C=CC2=CC(OC)=CC=C21 GGWCZBGAIGGTDA-UHFFFAOYSA-N 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- DPYDVZNEHYBCFU-UHFFFAOYSA-N 2-(2,2-dimethyl-4-naphthalen-1-ylchromen-7-yl)oxy-N-methylethanamine Chemical compound CC1(OC2=CC(=CC=C2C(=C1)C1=CC=CC2=CC=CC=C12)OCCNC)C DPYDVZNEHYBCFU-UHFFFAOYSA-N 0.000 description 1
- WFKIGTRPVAOPCF-UHFFFAOYSA-N 2-(2,2-dimethyl-4-naphthalen-1-ylchromen-7-yl)oxy-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.C1=CC=C2C(C=3C4=CC=C(C=C4OC(C)(C)C=3)OCCN(C)C)=CC=CC2=C1 WFKIGTRPVAOPCF-UHFFFAOYSA-N 0.000 description 1
- PANAMVNTFHDKBP-UHFFFAOYSA-N 2-[(2,2-dimethyl-4-naphthalen-1-yl-3,4-dihydrochromen-7-yl)oxy]-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.C1=CC=C2C(C3C4=CC=C(C=C4OC(C)(C)C3)OCCN(C)C)=CC=CC2=C1 PANAMVNTFHDKBP-UHFFFAOYSA-N 0.000 description 1
- CSHJJVSOVQKZSQ-UHFFFAOYSA-N 2-[(2,2-dimethyl-4-naphthalen-2-yl-3,4-dihydrochromen-7-yl)oxy]-n,n-diethylethanamine Chemical compound C1=CC=CC2=CC(C3C4=CC=C(C=C4OC(C)(C)C3)OCCN(CC)CC)=CC=C21 CSHJJVSOVQKZSQ-UHFFFAOYSA-N 0.000 description 1
- UHAHVPONPPLHNA-UHFFFAOYSA-N 2-[(2,2-dimethyl-4-naphthalen-2-yl-3,4-dihydrochromen-7-yl)oxy]-n-methylethanamine Chemical compound C1=CC=CC2=CC(C3C4=CC=C(C=C4OC(C)(C)C3)OCCNC)=CC=C21 UHAHVPONPPLHNA-UHFFFAOYSA-N 0.000 description 1
- VWVRASTUFJRTHW-UHFFFAOYSA-N 2-[3-(azetidin-3-yloxy)-4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound O=C(CN1C=C(C(OC2CNC2)=N1)C1=CN=C(NC2CC3=C(C2)C=CC=C3)N=C1)N1CCC2=C(C1)N=NN2 VWVRASTUFJRTHW-UHFFFAOYSA-N 0.000 description 1
- UHOUGSYSIOIXLL-UHFFFAOYSA-N 2-[4-(3-chloronaphthalen-1-yl)-2,2-dimethylchromen-7-yl]oxy-N,N-dimethylethanamine Chemical compound ClC=1C=C(C2=CC=CC=C2C=1)C1=CC(OC2=CC(=CC=C12)OCCN(C)C)(C)C UHOUGSYSIOIXLL-UHFFFAOYSA-N 0.000 description 1
- FIRGRLHXHRNLFU-UHFFFAOYSA-N 2-[4-(4-fluoronaphthalen-1-yl)-2,2-dimethylchromen-7-yl]oxy-n,n-dimethylethanamine Chemical compound C1=CC=C2C(C=3C4=CC=C(C=C4OC(C)(C)C=3)OCCN(C)C)=CC=C(F)C2=C1 FIRGRLHXHRNLFU-UHFFFAOYSA-N 0.000 description 1
- QUYBTVOGKRECIP-UHFFFAOYSA-N 2-[4-(6-methoxynaphthalen-2-yl)-2,2-dimethylchromen-7-yl]oxy-n,n-dimethylethanamine Chemical compound CN(C)CCOC1=CC=C2C(C3=CC4=CC=C(C=C4C=C3)OC)=CC(C)(C)OC2=C1 QUYBTVOGKRECIP-UHFFFAOYSA-N 0.000 description 1
- UYQSPYIUGPTILW-UHFFFAOYSA-N 2-[[4-(6-methoxynaphthalen-2-yl)-2,2-dimethyl-3,4-dihydrochromen-7-yl]oxy]-n,n-dimethylethanamine Chemical compound C1C(C)(C)OC2=CC(OCCN(C)C)=CC=C2C1C1=CC2=CC=C(OC)C=C2C=C1 UYQSPYIUGPTILW-UHFFFAOYSA-N 0.000 description 1
- CLLNGIARVQLUEW-UHFFFAOYSA-N 2-[[4-(6-methoxynaphthalen-2-yl)-2,2-dimethyl-3,4-dihydrochromen-7-yl]oxy]-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.C1C(C)(C)OC2=CC(OCCN(C)C)=CC=C2C1C1=CC2=CC=C(OC)C=C2C=C1 CLLNGIARVQLUEW-UHFFFAOYSA-N 0.000 description 1
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- SUVBZSPHWXZDLL-UHFFFAOYSA-N 4-(3-hydroxy-3-methyl-1-naphthalen-1-ylbutyl)benzene-1,3-diol Chemical compound C=1C=CC2=CC=CC=C2C=1C(CC(C)(O)C)C1=CC=C(O)C=C1O SUVBZSPHWXZDLL-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
- JKHCQUMNIXEDBL-UHFFFAOYSA-N 4-(6-methoxynaphthalen-2-yl)-2,2-dimethylchromen-7-ol Chemical compound OC1=CC=C2C(C3=CC4=CC=C(C=C4C=C3)OC)=CC(C)(C)OC2=C1 JKHCQUMNIXEDBL-UHFFFAOYSA-N 0.000 description 1
- CAIDTRYYHGGEMP-UHFFFAOYSA-N 6-[2-(dimethylamino)ethoxy]-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(OCCN(C)C)=CC=C21 CAIDTRYYHGGEMP-UHFFFAOYSA-N 0.000 description 1
- ZZOCLVONRFEUPJ-UHFFFAOYSA-N 7-hydroxy-4-(6-methoxynaphthalen-2-yl)chromen-2-one Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C1=CC2=CC=C(OC)C=C2C=C1 ZZOCLVONRFEUPJ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- IJVCBIVNEUVTNW-UHFFFAOYSA-M ClC=1C=C(C2=CC=CC=C2C=1)[Mg]Br Chemical compound ClC=1C=C(C2=CC=CC=C2C=1)[Mg]Br IJVCBIVNEUVTNW-UHFFFAOYSA-M 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 241000400611 Eucalyptus deanei Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000000578 anorexic effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 229940116592 central nervous system diagnostic radiopharmaceuticals Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- CMOYIKGRDXXXNU-UHFFFAOYSA-N ethyl 3-naphthalen-2-yl-3-oxopropanoate Chemical compound C1=CC=CC2=CC(C(=O)CC(=O)OCC)=CC=C21 CMOYIKGRDXXXNU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019256 formaldehyde Nutrition 0.000 description 1
- 229960004279 formaldehyde Drugs 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000005826 halohydrocarbons Chemical class 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- PYIXYEMKFUOLDQ-UHFFFAOYSA-N n-benzyl-2-chloro-n-methylethanamine;hydrochloride Chemical compound [Cl-].ClCC[NH+](C)CC1=CC=CC=C1 PYIXYEMKFUOLDQ-UHFFFAOYSA-N 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000002348 vinylic group Chemical group 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB30352/75A GB1497161A (en) | 1975-07-19 | 1975-07-19 | Naphthyl derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1072554A true CA1072554A (en) | 1980-02-26 |
Family
ID=10306288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA244,443A Expired CA1072554A (en) | 1975-07-19 | 1976-01-28 | Naphthyl derivatives |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4079066A (en, 2012) |
| JP (1) | JPS5212150A (en, 2012) |
| AU (1) | AU497409B2 (en, 2012) |
| BE (1) | BE837950A (en, 2012) |
| CA (1) | CA1072554A (en, 2012) |
| CH (1) | CH619208A5 (en, 2012) |
| DE (1) | DE2603178A1 (en, 2012) |
| DK (1) | DK34276A (en, 2012) |
| ES (1) | ES444765A1 (en, 2012) |
| FR (2) | FR2318628A1 (en, 2012) |
| GB (1) | GB1497161A (en, 2012) |
| IE (1) | IE42403B1 (en, 2012) |
| NL (1) | NL7600846A (en, 2012) |
| SE (1) | SE422794B (en, 2012) |
| ZA (1) | ZA761954B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1493998A (en) * | 1975-06-03 | 1977-12-07 | Beecham Group Ltd | Propanolamine derivatives |
| FR2608942B1 (fr) * | 1986-12-31 | 1991-01-11 | Centre Nat Rech Scient | Procede de preparation de systemes colloidaux dispersibles d'une substance, sous forme de nanocapsules |
| JPH07110853B2 (ja) * | 1990-09-07 | 1995-11-29 | シェリング・コーポレーション | 抗ウイルス化合物および抗高血圧化合物 |
| JPH06324511A (ja) * | 1993-05-14 | 1994-11-25 | Brother Ind Ltd | 感光性マイクロカプセル型トナー |
| JP3362745B2 (ja) * | 1993-07-28 | 2003-01-07 | ブラザー工業株式会社 | 感光性マイクロカプセル型トナー |
| CN101043886A (zh) * | 2004-10-22 | 2007-09-26 | 帝斯曼知识产权资产管理有限公司 | 用于预防和治疗与受损神经传递相关的失调症的新型试剂 |
| CN100393716C (zh) * | 2006-05-18 | 2008-06-11 | 中国药科大学 | 香豆素衍生物、其制备方法及作为α1受体拮抗剂的用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB953194A (en) * | 1960-11-08 | 1964-03-25 | Smith Kline French Lab | New benzylindene derivatives and method of preparing the same |
| US3388121A (en) * | 1964-12-16 | 1968-06-11 | Squibb & Sons Inc | Tetrahydrobenzocyclohexene and cycloheptene ethers |
-
1975
- 1975-07-19 GB GB30352/75A patent/GB1497161A/en not_active Expired
-
1976
- 1976-01-19 IE IE99/76A patent/IE42403B1/en unknown
- 1976-01-22 SE SE7600673A patent/SE422794B/xx unknown
- 1976-01-26 US US05/652,134 patent/US4079066A/en not_active Expired - Lifetime
- 1976-01-27 BE BE163838A patent/BE837950A/xx unknown
- 1976-01-28 DE DE19762603178 patent/DE2603178A1/de not_active Withdrawn
- 1976-01-28 FR FR7602247A patent/FR2318628A1/fr active Granted
- 1976-01-28 NL NL7600846A patent/NL7600846A/xx not_active Application Discontinuation
- 1976-01-28 DK DK34276A patent/DK34276A/da not_active Application Discontinuation
- 1976-01-28 CA CA244,443A patent/CA1072554A/en not_active Expired
- 1976-01-29 AU AU10664/76A patent/AU497409B2/en not_active Expired
- 1976-01-29 JP JP51008860A patent/JPS5212150A/ja active Pending
- 1976-01-29 ES ES444765A patent/ES444765A1/es not_active Expired
- 1976-01-29 CH CH112076A patent/CH619208A5/de not_active IP Right Cessation
- 1976-03-31 ZA ZA761954A patent/ZA761954B/xx unknown
- 1976-05-05 FR FR7613359A patent/FR2318624A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2318624B1 (en, 2012) | 1979-06-29 |
| ES444765A1 (es) | 1977-12-01 |
| GB1497161A (en) | 1978-01-05 |
| FR2318628A1 (fr) | 1977-02-18 |
| SE422794B (sv) | 1982-03-29 |
| IE42403L (en) | 1977-01-19 |
| AU1066476A (en) | 1977-08-04 |
| DE2603178A1 (de) | 1977-02-03 |
| NL7600846A (nl) | 1977-01-21 |
| US4079066A (en) | 1978-03-14 |
| JPS5212150A (en) | 1977-01-29 |
| FR2318628B1 (en, 2012) | 1979-09-28 |
| IE42403B1 (en) | 1980-07-30 |
| ZA761954B (en) | 1977-04-27 |
| BE837950A (fr) | 1976-07-27 |
| AU497409B2 (en) | 1978-12-14 |
| SE7600673L (sv) | 1977-01-20 |
| DK34276A (da) | 1977-01-20 |
| FR2318624A1 (fr) | 1977-02-18 |
| CH619208A5 (en, 2012) | 1980-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |