IE43144B1 - Aryltetralins - Google Patents
AryltetralinsInfo
- Publication number
- IE43144B1 IE43144B1 IE1555/76A IE155576A IE43144B1 IE 43144 B1 IE43144 B1 IE 43144B1 IE 1555/76 A IE1555/76 A IE 1555/76A IE 155576 A IE155576 A IE 155576A IE 43144 B1 IE43144 B1 IE 43144B1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- group
- compound
- hydrogen atom
- compound according
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003944 tolyl group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- -1 methanesulphonyl Chemical group 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000012320 chlorinating reagent Substances 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000005518 carboxamido group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000002524 organometallic group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 54
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract description 8
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 abstract description 4
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract description 4
- 150000002902 organometallic compounds Chemical class 0.000 abstract description 4
- 230000017858 demethylation Effects 0.000 abstract description 3
- 238000010520 demethylation reaction Methods 0.000 abstract description 3
- 238000006266 etherification reaction Methods 0.000 abstract description 3
- 238000005984 hydrogenation reaction Methods 0.000 abstract description 3
- 230000007062 hydrolysis Effects 0.000 abstract description 3
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract description 2
- 239000000935 antidepressant agent Substances 0.000 abstract description 2
- 229940005513 antidepressants Drugs 0.000 abstract description 2
- 238000010561 standard procedure Methods 0.000 abstract description 2
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 abstract description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 2
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 abstract 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 1
- 230000001539 anorectic effect Effects 0.000 abstract 1
- 150000003934 aromatic aldehydes Chemical class 0.000 abstract 1
- 238000005660 chlorination reaction Methods 0.000 abstract 1
- 206010061428 decreased appetite Diseases 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000000468 ketone group Chemical group 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 229940014800 succinic anhydride Drugs 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 22
- 235000019441 ethanol Nutrition 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000000284 extract Substances 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- 230000008020 evaporation Effects 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 9
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 9
- 239000010410 layer Substances 0.000 description 8
- 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 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 5
- ONPCFEBOBYWDCR-UHFFFAOYSA-N 4-(4-chlorophenyl)-7-[2-(dimethylamino)ethoxy]-2,2-dimethyl-3,4-dihydronaphthalen-1-one Chemical compound C1C(C)(C)C(=O)C2=CC(OCCN(C)C)=CC=C2C1C1=CC=C(Cl)C=C1 ONPCFEBOBYWDCR-UHFFFAOYSA-N 0.000 description 5
- QIKBNQQHBYVGAY-UHFFFAOYSA-N 4-(4-chlorophenyl)-7-hydroxy-2,2-dimethyl-3,4-dihydronaphthalen-1-one Chemical compound C12=CC=C(O)C=C2C(=O)C(C)(C)CC1C1=CC=C(Cl)C=C1 QIKBNQQHBYVGAY-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 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
- 239000003054 catalyst Substances 0.000 description 5
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 5
- 230000036651 mood Effects 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 229940124332 anorexigenic agent Drugs 0.000 description 4
- 239000002830 appetite depressant Substances 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 230000000694 effects Effects 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
- 230000000051 modifying effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 229910052723 transition metal Inorganic materials 0.000 description 4
- 150000003624 transition metals Chemical class 0.000 description 4
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 3
- XNTNPKXCRBTDTR-UHFFFAOYSA-N 2,2-dimethyl-3,4-dihydronaphthalen-1-one Chemical compound C1=CC=C2C(=O)C(C)(C)CCC2=C1 XNTNPKXCRBTDTR-UHFFFAOYSA-N 0.000 description 3
- RYFKFBLPJVNYAQ-UHFFFAOYSA-N 2-[[5-(4-chlorophenyl)-7,7-dimethyl-8-methylidene-5,6-dihydronaphthalen-2-yl]oxy]-n,n-dimethylethanamine Chemical compound C1C(C)(C)C(=C)C2=CC(OCCN(C)C)=CC=C2C1C1=CC=C(Cl)C=C1 RYFKFBLPJVNYAQ-UHFFFAOYSA-N 0.000 description 3
- MZPKBAZXHFGVMZ-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-7-hydroxy-2,2-dimethyl-3,4-dihydronaphthalen-1-one Chemical compound C12=CC=C(O)C=C2C(=O)C(C)(C)CC1C1=CC=C(Cl)C(Cl)=C1 MZPKBAZXHFGVMZ-UHFFFAOYSA-N 0.000 description 3
- OPTYGJRPBDJVAN-UHFFFAOYSA-N 4-(4-chlorophenyl)-2,2-dimethyl-7-(oxiran-2-ylmethoxy)-3,4-dihydronaphthalen-1-one Chemical compound C12=CC=C(OCC3OC3)C=C2C(=O)C(C)(C)CC1C1=CC=C(Cl)C=C1 OPTYGJRPBDJVAN-UHFFFAOYSA-N 0.000 description 3
- YJLRKDDVYGQCKJ-UHFFFAOYSA-N 4-(4-chlorophenyl)-7-[2-(dimethylamino)ethoxy]-2,2-dimethyl-3,4-dihydro-1h-naphthalen-1-ol Chemical compound C1C(C)(C)C(O)C2=CC(OCCN(C)C)=CC=C2C1C1=CC=C(Cl)C=C1 YJLRKDDVYGQCKJ-UHFFFAOYSA-N 0.000 description 3
- XUPWESVHXCSXAO-UHFFFAOYSA-N 7-methoxy-4-[3-(trifluoromethyl)phenyl]-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CC(=O)C2=CC(OC)=CC=C2C1C1=CC=CC(C(F)(F)F)=C1 XUPWESVHXCSXAO-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 3
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 230000037406 food intake Effects 0.000 description 3
- 235000012631 food intake Nutrition 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 3
- 229960003147 reserpine Drugs 0.000 description 3
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 2
- VNJNAVOALRVLBT-UHFFFAOYSA-N 2-[[5-(4-chlorophenyl)-7,7,8-trimethyl-6,8-dihydro-5h-naphthalen-2-yl]oxy]-n,n-dimethylethanamine Chemical compound C1C(C)(C)C(C)C2=CC(OCCN(C)C)=CC=C2C1C1=CC=C(Cl)C=C1 VNJNAVOALRVLBT-UHFFFAOYSA-N 0.000 description 2
- PKGVTFHNGUVKOK-UHFFFAOYSA-N 4-(4-chlorophenyl)-7-[2-hydroxy-3-(methylamino)propoxy]-2,2-dimethyl-3,4-dihydronaphthalen-1-one Chemical compound C1C(C)(C)C(=O)C2=CC(OCC(O)CNC)=CC=C2C1C1=CC=C(Cl)C=C1 PKGVTFHNGUVKOK-UHFFFAOYSA-N 0.000 description 2
- UXRGRGMPNCJELX-UHFFFAOYSA-N 7-[2-(dimethylamino)ethoxy]-4-[3-(trifluoromethyl)phenyl]-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CC(=O)C2=CC(OCCN(C)C)=CC=C2C1C1=CC=CC(C(F)(F)F)=C1 UXRGRGMPNCJELX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 2
- 244000166102 Eucalyptus leucoxylon Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000002891 anorexigenic effect Effects 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 2
- YZWFMQIRFLXRAA-UHFFFAOYSA-N ethyl 3-(4-methoxyphenyl)-3-[3-(trifluoromethyl)phenyl]propanoate Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(CC(=O)OCC)C1=CC=C(OC)C=C1 YZWFMQIRFLXRAA-UHFFFAOYSA-N 0.000 description 2
- VLGXHSYKIDVGQN-UHFFFAOYSA-N ethyl 4-(4-chlorophenyl)-2,2-dimethylbut-3-enoate Chemical compound CCOC(=O)C(C)(C)C=CC1=CC=C(Cl)C=C1 VLGXHSYKIDVGQN-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
- 239000004533 oil dispersion Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000007892 solid unit dosage form Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
- IPHFEAMSIOVYCA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene;hydrochloride Chemical compound Cl.C1=CC=C2CCCCC2=C1 IPHFEAMSIOVYCA-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
- DPZHKLJPVMYFCU-UHFFFAOYSA-N 2-(5-bromopyridin-2-yl)acetonitrile Chemical compound BrC1=CC=C(CC#N)N=C1 DPZHKLJPVMYFCU-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
- ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 description 1
- RUJYJCANMOTJMO-UHFFFAOYSA-N 3-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC(C(Cl)=O)=C1 RUJYJCANMOTJMO-UHFFFAOYSA-N 0.000 description 1
- GKCHRDAIENCWNJ-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-2,2-dimethyl-7-(oxiran-2-ylmethoxy)-3,4-dihydronaphthalen-1-one Chemical compound C12=CC=C(OCC3OC3)C=C2C(=O)C(C)(C)CC1C1=CC=C(Cl)C(Cl)=C1 GKCHRDAIENCWNJ-UHFFFAOYSA-N 0.000 description 1
- DFMXIQREUNTDQT-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-7-[2-(dimethylamino)ethoxy]-2,2-dimethyl-3,4-dihydronaphthalen-1-one Chemical compound C1C(C)(C)C(=O)C2=CC(OCCN(C)C)=CC=C2C1C1=CC=C(Cl)C(Cl)=C1 DFMXIQREUNTDQT-UHFFFAOYSA-N 0.000 description 1
- UFZMBBWQVDIGOU-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-(4-methoxyphenyl)-2,2-dimethylbutanoic acid Chemical compound C1=CC(OC)=CC=C1C(CC(C)(C)C(O)=O)C1=CC=C(Cl)C=C1 UFZMBBWQVDIGOU-UHFFFAOYSA-N 0.000 description 1
- DQWPQKFHUCDRPK-UHFFFAOYSA-N 4-(4-chlorophenyl)-7-methoxy-2,2-dimethyl-3,4-dihydronaphthalen-1-one Chemical compound C1C(C)(C)C(=O)C2=CC(OC)=CC=C2C1C1=CC=C(Cl)C=C1 DQWPQKFHUCDRPK-UHFFFAOYSA-N 0.000 description 1
- SQKXKCVKYCVKQE-UHFFFAOYSA-N 4-(4-fluorophenyl)-7-hydroxy-2,2-dimethyl-3,4-dihydronaphthalen-1-one Chemical compound C12=CC=C(O)C=C2C(=O)C(C)(C)CC1C1=CC=C(F)C=C1 SQKXKCVKYCVKQE-UHFFFAOYSA-N 0.000 description 1
- PEKTYKFECPGDGZ-UHFFFAOYSA-N 4-(4-methoxyphenyl)-4-[3-(trifluoromethyl)phenyl]butanoic acid Chemical compound C1=CC(OC)=CC=C1C(CCC(O)=O)C1=CC=CC(C(F)(F)F)=C1 PEKTYKFECPGDGZ-UHFFFAOYSA-N 0.000 description 1
- AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- LEVUKQKRGHDMMC-UHFFFAOYSA-N 7-[2-(dimethylamino)ethoxy]-2,2-dimethyl-4-[3-(trifluoromethyl)phenyl]-3,4-dihydronaphthalen-1-one Chemical compound C1C(C)(C)C(=O)C2=CC(OCCN(C)C)=CC=C2C1C1=CC=CC(C(F)(F)F)=C1 LEVUKQKRGHDMMC-UHFFFAOYSA-N 0.000 description 1
- ZXANPCSSHYGIJV-UHFFFAOYSA-N 7-[2-(dimethylamino)ethoxy]-2,2-dimethyl-4-[3-(trifluoromethyl)phenyl]-3,4-dihydronaphthalen-1-one 7-methoxy-4-[3-(trifluoromethyl)phenyl]-3,4-dihydro-2H-naphthalen-1-one Chemical compound FC(C=1C=C(C=CC1)C1CCC(C2=CC(=CC=C12)OC)=O)(F)F.FC(C=1C=C(C=CC1)C1CC(C(C2=CC(=CC=C12)OCCN(C)C)=O)(C)C)(F)F ZXANPCSSHYGIJV-UHFFFAOYSA-N 0.000 description 1
- MDBLSGRQIIHZMT-UHFFFAOYSA-N 7-[2-(dimethylamino)ethoxy]-4-(4-fluorophenyl)-2,2-dimethyl-3,4-dihydronaphthalen-1-one Chemical compound C1C(C)(C)C(=O)C2=CC(OCCN(C)C)=CC=C2C1C1=CC=C(F)C=C1 MDBLSGRQIIHZMT-UHFFFAOYSA-N 0.000 description 1
- IXWGJMPZMGNDDK-UHFFFAOYSA-N 7-hydroxy-4-[3-(trifluoromethyl)phenyl]-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CC(=O)C2=CC(O)=CC=C2C1C1=CC=CC(C(F)(F)F)=C1 IXWGJMPZMGNDDK-UHFFFAOYSA-N 0.000 description 1
- NKIPNIXPQYLHLH-UHFFFAOYSA-N 7-methoxy-2,2-dimethyl-4-[3-(trifluoromethyl)phenyl]-3,4-dihydronaphthalen-1-one Chemical compound C1C(C)(C)C(=O)C2=CC(OC)=CC=C2C1C1=CC=CC(C(F)(F)F)=C1 NKIPNIXPQYLHLH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-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
- 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
- 241000700159 Rattus Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 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
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000002474 dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000005843 halogen group Chemical group 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
- 230000002631 hypothermal effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- JNTMWPCEVGHVML-UHFFFAOYSA-N n-benzyl-2-chloro-n-methylethanamine Chemical compound ClCCN(C)CC1=CC=CC=C1 JNTMWPCEVGHVML-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 150000002888 oleic acid derivatives Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- URPBOJNAKRFRDF-UHFFFAOYSA-N potassium;iodomethane;2-methylpropan-2-olate Chemical compound [K+].IC.CC(C)(C)[O-] URPBOJNAKRFRDF-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- UWYJUJXBOUUQMY-UHFFFAOYSA-M sodium ethyl 4-(4-chlorophenyl)-2,2-dimethylbut-3-enoate acetate Chemical compound C(C)(=O)[O-].[Na+].ClC1=CC=C(C=C1)C=CC(C(=O)OCC)(C)C UWYJUJXBOUUQMY-UHFFFAOYSA-M 0.000 description 1
- 239000008259 solid foam Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007070 tosylation reaction Methods 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/52—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
- C07C57/60—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings having unsaturation outside the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB30923/75A GB1493848A (en) | 1975-07-24 | 1975-07-24 | Aryltetralins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43144L IE43144L (en) | 1977-01-24 |
| IE43144B1 true IE43144B1 (en) | 1980-12-31 |
Family
ID=10315210
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1555/76A IE43144B1 (en) | 1975-07-24 | 1976-07-14 | Aryltetralins |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4322370A (enExample) |
| JP (1) | JPS5214756A (enExample) |
| AT (1) | AT347442B (enExample) |
| AU (1) | AU500207B2 (enExample) |
| BE (1) | BE844300A (enExample) |
| CA (1) | CA1072119A (enExample) |
| CH (3) | CH624382A5 (enExample) |
| DE (1) | DE2632862A1 (enExample) |
| DK (1) | DK334976A (enExample) |
| ES (2) | ES450113A1 (enExample) |
| FR (1) | FR2318625A1 (enExample) |
| GB (1) | GB1493848A (enExample) |
| HU (1) | HU177289B (enExample) |
| IE (1) | IE43144B1 (enExample) |
| IL (1) | IL50058A (enExample) |
| NL (1) | NL7607812A (enExample) |
| NZ (1) | NZ181467A (enExample) |
| SE (1) | SE7608119L (enExample) |
| ZA (1) | ZA764351B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2507181A1 (fr) | 1981-06-05 | 1982-12-10 | Sanofi Sa | Nouveaux ethers de phenol actifs sur le systeme cardiovasculaire, leur procede de preparation et leur utilisation dans des medicaments |
| US4839104A (en) * | 1987-06-11 | 1989-06-13 | Pfizer, Inc. | Process for preparing sertraline intermediates |
| ES2064228B1 (es) * | 1992-10-19 | 1995-09-01 | Uriach & Cia Sa J | Nuevas tetralonas con actividad farmacologica, composiciones que las contienen y procedimiento para su preparacion. |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2820817A (en) * | 1954-02-04 | 1958-01-21 | Mcneilab Inc | Oxygenated indan compounds and method of making the same |
| US3565956A (en) * | 1964-10-16 | 1971-02-23 | Sterling Drug Inc | Amino-lower-alkoxy-5-alkylidene-dibenzo(a,d)cycloheptenes |
| US3388121A (en) * | 1964-12-16 | 1968-06-11 | Squibb & Sons Inc | Tetrahydrobenzocyclohexene and cycloheptene ethers |
| US3476767A (en) * | 1965-10-11 | 1969-11-04 | Ciba Geigy Corp | 1,2-diaryl - 6 - tertiary amino lower-alkoxy-3,4-dihydro naphthalenes |
| US3641152A (en) * | 1968-09-23 | 1972-02-08 | Warner Lambert Pharmaceutical | 3 4-dihydronaphthalenoneoxy-2-hydroxy-propylamines |
| US3671530A (en) * | 1970-08-27 | 1972-06-20 | Miles Lab | Certain substituted 1,3-bisdilower-alkylaminoethoxy-indans |
| US3988475A (en) * | 1974-02-05 | 1976-10-26 | Istituto Luso Farmaco D'italia S.R.L. | Phenoxyalkylamines |
-
1975
- 1975-07-24 GB GB30923/75A patent/GB1493848A/en not_active Expired
-
1976
- 1976-07-14 NZ NZ181467A patent/NZ181467A/xx unknown
- 1976-07-14 NL NL7607812A patent/NL7607812A/xx not_active Application Discontinuation
- 1976-07-14 IE IE1555/76A patent/IE43144B1/en unknown
- 1976-07-15 SE SE7608119A patent/SE7608119L/xx not_active Application Discontinuation
- 1976-07-16 FR FR7621755A patent/FR2318625A1/fr active Granted
- 1976-07-16 IL IL50058A patent/IL50058A/xx unknown
- 1976-07-19 BE BE169050A patent/BE844300A/xx unknown
- 1976-07-21 AT AT537176A patent/AT347442B/de not_active IP Right Cessation
- 1976-07-21 ZA ZA764351A patent/ZA764351B/xx unknown
- 1976-07-21 DE DE19762632862 patent/DE2632862A1/de not_active Withdrawn
- 1976-07-22 JP JP51087680A patent/JPS5214756A/ja active Pending
- 1976-07-23 ES ES450113A patent/ES450113A1/es not_active Expired
- 1976-07-23 CH CH947976A patent/CH624382A5/de not_active IP Right Cessation
- 1976-07-23 DK DK334976A patent/DK334976A/da unknown
- 1976-07-23 CA CA257,675A patent/CA1072119A/en not_active Expired
- 1976-07-23 HU HU76BE1264A patent/HU177289B/hu unknown
- 1976-07-26 AU AU16254/76A patent/AU500207B2/en not_active Expired
-
1977
- 1977-07-27 ES ES461082A patent/ES461082A1/es not_active Expired
-
1978
- 1978-02-13 US US05/877,303 patent/US4322370A/en not_active Expired - Lifetime
-
1980
- 1980-05-29 CH CH419380A patent/CH625781A5/de not_active IP Right Cessation
- 1980-05-29 CH CH419480A patent/CH625502A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AU1625476A (en) | 1978-02-02 |
| ZA764351B (en) | 1977-07-27 |
| CH625502A5 (enExample) | 1981-09-30 |
| CH625781A5 (enExample) | 1981-10-15 |
| AU500207B2 (en) | 1979-05-10 |
| BE844300A (fr) | 1977-01-19 |
| IL50058A0 (en) | 1976-09-30 |
| HU177289B (en) | 1981-09-28 |
| AT347442B (de) | 1978-12-27 |
| ATA537176A (de) | 1978-05-15 |
| ES450113A1 (es) | 1977-12-01 |
| GB1493848A (en) | 1977-11-30 |
| DE2632862A1 (de) | 1977-02-03 |
| IE43144L (en) | 1977-01-24 |
| FR2318625B1 (enExample) | 1978-12-15 |
| SE7608119L (sv) | 1977-01-25 |
| DK334976A (da) | 1977-01-25 |
| CH624382A5 (enExample) | 1981-07-31 |
| ES461082A1 (es) | 1978-06-16 |
| IL50058A (en) | 1979-10-31 |
| NZ181467A (en) | 1978-09-25 |
| US4322370A (en) | 1982-03-30 |
| FR2318625A1 (fr) | 1977-02-18 |
| CA1072119A (en) | 1980-02-19 |
| JPS5214756A (en) | 1977-02-03 |
| NL7607812A (nl) | 1977-01-26 |
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