DE2533885A1 - Chroman-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate - Google Patents
Chroman-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparateInfo
- Publication number
- DE2533885A1 DE2533885A1 DE19752533885 DE2533885A DE2533885A1 DE 2533885 A1 DE2533885 A1 DE 2533885A1 DE 19752533885 DE19752533885 DE 19752533885 DE 2533885 A DE2533885 A DE 2533885A DE 2533885 A1 DE2533885 A1 DE 2533885A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- radical
- compound
- compounds
- dimethyl
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 151
- 238000002360 preparation method Methods 0.000 title claims description 16
- 238000000034 method Methods 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 4
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical class C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 title description 8
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 alkylene radical Chemical group 0.000 claims description 68
- 150000003839 salts Chemical class 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 150000003254 radicals Chemical class 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 238000006073 displacement reaction Methods 0.000 claims description 7
- 230000000269 nucleophilic effect Effects 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000003944 tolyl group Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- FRYSRIHJRHPXIK-UHFFFAOYSA-N 2-[[2,2-dimethyl-4-[4-(trifluoromethyl)phenyl]-3,4-dihydrochromen-7-yl]oxy]-n,n-dimethylethanamine Chemical compound C1C(C)(C)OC2=CC(OCCN(C)C)=CC=C2C1C1=CC=C(C(F)(F)F)C=C1 FRYSRIHJRHPXIK-UHFFFAOYSA-N 0.000 claims description 2
- BKDYMODQNOBTPH-UHFFFAOYSA-N 2-[[2,2-dimethyl-4-[4-(trifluoromethyl)phenyl]-3,4-dihydrochromen-7-yl]oxy]-n-methylethanamine Chemical compound C1C(C)(C)OC2=CC(OCCNC)=CC=C2C1C1=CC=C(C(F)(F)F)C=C1 BKDYMODQNOBTPH-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 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 description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 2
- FBCURPOHRNRWHW-UHFFFAOYSA-N 2-[[2,2-dimethyl-4-[3-(trifluoromethyl)phenyl]-3,4-dihydrochromen-7-yl]oxy]-n-methylethanamine Chemical compound C1C(C)(C)OC2=CC(OCCNC)=CC=C2C1C1=CC=CC(C(F)(F)F)=C1 FBCURPOHRNRWHW-UHFFFAOYSA-N 0.000 claims 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 174
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 58
- 239000003921 oil Substances 0.000 description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 45
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 40
- 239000002904 solvent Substances 0.000 description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 22
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 21
- 235000019341 magnesium sulphate Nutrition 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 19
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 18
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 17
- 239000012071 phase Substances 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000012259 ether extract Substances 0.000 description 12
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- 239000012230 colorless oil Substances 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- 229910052749 magnesium Inorganic materials 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 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 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 239000005909 Kieselgur Substances 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical group [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Chemical group 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 239000007787 solid Substances 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
- ZTFCHKNKFJKXJG-UHFFFAOYSA-N 2,2-dimethyl-4-[3-(trifluoromethyl)phenyl]-3,4-dihydrochromen-7-ol Chemical compound C12=CC=C(O)C=C2OC(C)(C)CC1C1=CC=CC(C(F)(F)F)=C1 ZTFCHKNKFJKXJG-UHFFFAOYSA-N 0.000 description 3
- SWSDEPRAFMWJSG-UHFFFAOYSA-N 2,2-dimethyl-4-[4-(trifluoromethyl)phenyl]-3,4-dihydrochromen-7-ol Chemical compound C12=CC=C(O)C=C2OC(C)(C)CC1C1=CC=C(C(F)(F)F)C=C1 SWSDEPRAFMWJSG-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 3
- UDENHAVWQFDPTL-UHFFFAOYSA-N 6-[2-(dimethylamino)ethoxy]-3,3-dimethyl-2,4-dihydronaphthalen-1-one Chemical compound CC1(CC(C2=CC=C(C=C2C1)OCCN(C)C)=O)C UDENHAVWQFDPTL-UHFFFAOYSA-N 0.000 description 3
- PHEWNYMTGPOCOP-UHFFFAOYSA-N 7-hydroxy-2,2-dimethyl-3h-chromen-4-one Chemical compound C1=C(O)C=C2OC(C)(C)CC(=O)C2=C1 PHEWNYMTGPOCOP-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 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
- 230000036528 appetite Effects 0.000 description 3
- 235000019789 appetite Nutrition 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 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
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 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
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 3
- NNMBNYHMJRJUBC-UHFFFAOYSA-N 1-bromo-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(Br)=C1 NNMBNYHMJRJUBC-UHFFFAOYSA-N 0.000 description 2
- KPPOOSMPPZFJOZ-UHFFFAOYSA-N 2,2-dimethyl-4-thiophen-2-yl-3,4-dihydrochromen-7-ol Chemical compound C12=CC=C(O)C=C2OC(C)(C)CC1C1=CC=CS1 KPPOOSMPPZFJOZ-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- YNSRNHXETUQRND-UHFFFAOYSA-N 7-hydroxy-4-thiophen-2-yl-3,4-dihydrochromen-2-one Chemical compound C1C(=O)OC2=CC(O)=CC=C2C1C1=CC=CS1 YNSRNHXETUQRND-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WSWOKFODOPIESP-UHFFFAOYSA-M [Br-].FC(F)(F)C1=CC=CC([Mg+])=C1 Chemical compound [Br-].FC(F)(F)C1=CC=CC([Mg+])=C1 WSWOKFODOPIESP-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 230000004596 appetite loss Effects 0.000 description 2
- 125000005518 carboxamido group Chemical group 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 235000012631 food intake Nutrition 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 235000021266 loss of appetite Nutrition 0.000 description 2
- 208000019017 loss of appetite Diseases 0.000 description 2
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical group [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 2
- 229910001623 magnesium bromide Inorganic materials 0.000 description 2
- 229910001629 magnesium chloride Chemical group 0.000 description 2
- BLQJIBCZHWBKSL-UHFFFAOYSA-L magnesium iodide Chemical group [Mg+2].[I-].[I-] BLQJIBCZHWBKSL-UHFFFAOYSA-L 0.000 description 2
- 229910001641 magnesium iodide Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- 230000036651 mood Effects 0.000 description 2
- STYDBERWROZGHV-UHFFFAOYSA-N n-(2-chloroethyl)-2-phenylethanamine;hydrochloride Chemical compound Cl.ClCCNCCC1=CC=CC=C1 STYDBERWROZGHV-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DVWZHSYLNWVSET-UHFFFAOYSA-N 1-(4-chlorophenyl)-6-methoxy-3,3-dimethyl-2,4-dihydro-1H-naphthalene Chemical compound ClC1=CC=C(C=C1)C1CC(CC2=CC(=CC=C12)OC)(C)C DVWZHSYLNWVSET-UHFFFAOYSA-N 0.000 description 1
- XLQSXGGDTHANLN-UHFFFAOYSA-N 1-bromo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Br)C=C1 XLQSXGGDTHANLN-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
- NAFSRHGLFHCJDX-UHFFFAOYSA-N 2,2-dimethyl-4-[3-(trifluoromethyl)phenyl]chromen-7-ol Chemical compound C=1C(C)(C)OC2=CC(O)=CC=C2C=1C1=CC=CC(C(F)(F)F)=C1 NAFSRHGLFHCJDX-UHFFFAOYSA-N 0.000 description 1
- STFVJAGVPMVNJE-UHFFFAOYSA-N 2,2-dimethyl-4-phenyl-3,4-dihydrochromen-7-ol Chemical compound C12=CC=C(O)C=C2OC(C)(C)CC1C1=CC=CC=C1 STFVJAGVPMVNJE-UHFFFAOYSA-N 0.000 description 1
- QQAKLWJRWRKLOD-UHFFFAOYSA-N 2,2-dimethyl-4-phenylchromen-7-ol Chemical compound C=1C(C)(C)OC2=CC(O)=CC=C2C=1C1=CC=CC=C1 QQAKLWJRWRKLOD-UHFFFAOYSA-N 0.000 description 1
- FVZYNVBBMYYCRM-UHFFFAOYSA-N 2,2-dimethyl-7-phenylmethoxy-4-[3-(trifluoromethyl)phenyl]chromene Chemical compound C=1C=C2C(C=3C=C(C=CC=3)C(F)(F)F)=CC(C)(C)OC2=CC=1OCC1=CC=CC=C1 FVZYNVBBMYYCRM-UHFFFAOYSA-N 0.000 description 1
- PJYFNHKOKCBYBK-UHFFFAOYSA-N 2,2-dimethyl-7-phenylmethoxy-4-[4-(trifluoromethyl)phenyl]chromene Chemical compound C=1C=C2C(C=3C=CC(=CC=3)C(F)(F)F)=CC(C)(C)OC2=CC=1OCC1=CC=CC=C1 PJYFNHKOKCBYBK-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
- XUASNZWPHKUGCN-UHFFFAOYSA-N 2-(2,2-dimethyl-4-phenylchromen-7-yl)oxy-n,n-dimethylethanamine Chemical compound C=1C(C)(C)OC2=CC(OCCN(C)C)=CC=C2C=1C1=CC=CC=C1 XUASNZWPHKUGCN-UHFFFAOYSA-N 0.000 description 1
- VQSNXZOPIJCUFG-UHFFFAOYSA-N 2-[(2,2-dimethyl-4-phenyl-3,4-dihydrochromen-7-yl)oxy]-n,n-dimethylpropan-2-amine;hydrobromide Chemical compound Br.C1C(C)(C)OC2=CC(OC(C)(C)N(C)C)=CC=C2C1C1=CC=CC=C1 VQSNXZOPIJCUFG-UHFFFAOYSA-N 0.000 description 1
- LCAREYRLVPUKTC-UHFFFAOYSA-N 2-[(2,2-dimethyl-4-thiophen-2-yl-3,4-dihydrochromen-7-yl)oxy]-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.C1C(C)(C)OC2=CC(OCCN(C)C)=CC=C2C1C1=CC=CS1 LCAREYRLVPUKTC-UHFFFAOYSA-N 0.000 description 1
- KZMZRWWFNUMBNP-UHFFFAOYSA-N 2-[2,2-dimethyl-4-[3-(trifluoromethyl)phenyl]chromen-7-yl]oxy-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.C=1C(C)(C)OC2=CC(OCCN(C)C)=CC=C2C=1C1=CC=CC(C(F)(F)F)=C1 KZMZRWWFNUMBNP-UHFFFAOYSA-N 0.000 description 1
- GBVYWHZORWYLMX-UHFFFAOYSA-N 2-[2,2-dimethyl-4-[[3-(trifluoromethyl)phenyl]methyl]chromen-7-yl]oxy-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.C=1C(C)(C)OC2=CC(OCCN(C)C)=CC=C2C=1CC1=CC=CC(C(F)(F)F)=C1 GBVYWHZORWYLMX-UHFFFAOYSA-N 0.000 description 1
- LJBQWGHTKQKWIC-UHFFFAOYSA-N 2-[4-(4-bromophenyl)-2,2-dimethylchromen-7-yl]oxy-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.C=1C(C)(C)OC2=CC(OCCN(C)C)=CC=C2C=1C1=CC=C(Br)C=C1 LJBQWGHTKQKWIC-UHFFFAOYSA-N 0.000 description 1
- OUCHPHSRSDFLOS-UHFFFAOYSA-N 2-[[2,2-dimethyl-3-[3-(trifluoromethyl)phenyl]-3,4-dihydrochromen-7-yl]oxy]-n-methylethanamine Chemical compound CC1(C)OC2=CC(OCCNC)=CC=C2CC1C1=CC=CC(C(F)(F)F)=C1 OUCHPHSRSDFLOS-UHFFFAOYSA-N 0.000 description 1
- JXMMPZKBOUKGPG-UHFFFAOYSA-N 2-[[2,2-dimethyl-4-[3-(trifluoromethyl)phenyl]-3,4-dihydrochromen-7-yl]oxy]-n,n-dimethylethanamine Chemical compound C1C(C)(C)OC2=CC(OCCN(C)C)=CC=C2C1C1=CC=CC(C(F)(F)F)=C1 JXMMPZKBOUKGPG-UHFFFAOYSA-N 0.000 description 1
- SZOTUEQJTZTBEI-UHFFFAOYSA-N 2-[[2,2-dimethyl-4-[3-(trifluoromethyl)phenyl]-3,4-dihydrochromen-7-yl]oxy]acetonitrile Chemical compound C12=CC=C(OCC#N)C=C2OC(C)(C)CC1C1=CC=CC(C(F)(F)F)=C1 SZOTUEQJTZTBEI-UHFFFAOYSA-N 0.000 description 1
- MJCVZCDGQCMGKD-UHFFFAOYSA-N 2-[[2,2-dimethyl-4-[3-(trifluoromethyl)phenyl]-3,4-dihydrochromen-7-yl]oxy]ethanamine Chemical compound C12=CC=C(OCCN)C=C2OC(C)(C)CC1C1=CC=CC(C(F)(F)F)=C1 MJCVZCDGQCMGKD-UHFFFAOYSA-N 0.000 description 1
- RHPRTHYFROQWDJ-UHFFFAOYSA-N 2-[[2,2-dimethyl-4-[4-(trifluoromethyl)phenyl]-3,4-dihydrochromen-7-yl]oxy]-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.C1C(C)(C)OC2=CC(OCCN(C)C)=CC=C2C1C1=CC=C(C(F)(F)F)C=C1 RHPRTHYFROQWDJ-UHFFFAOYSA-N 0.000 description 1
- BSYLMFFTRBRBJM-UHFFFAOYSA-N 2-[[2,2-dimethyl-4-[4-(trifluoromethyl)phenyl]-3,4-dihydrochromen-7-yl]oxy]-n-methylethanamine;hydrochloride Chemical compound Cl.C1C(C)(C)OC2=CC(OCCNC)=CC=C2C1C1=CC=C(C(F)(F)F)C=C1 BSYLMFFTRBRBJM-UHFFFAOYSA-N 0.000 description 1
- RJSMWGKNCTUMCK-UHFFFAOYSA-N 2-[[2,2-dimethyl-4-[4-(trifluoromethyl)phenyl]-3,4-dihydrochromen-7-yl]oxy]ethanamine Chemical compound C12=CC=C(OCCN)C=C2OC(C)(C)CC1C1=CC=C(C(F)(F)F)C=C1 RJSMWGKNCTUMCK-UHFFFAOYSA-N 0.000 description 1
- OJBSBOPCVJQYHF-UHFFFAOYSA-N 2-[[2,2-dimethyl-4-[[3-(trifluoromethyl)phenyl]methyl]-3,4-dihydrochromen-7-yl]oxy]-N,N-dimethylethanamine hydrochloride Chemical compound Cl.CN(C)CCOC1=CC=C2C(CC3=CC(=CC=C3)C(F)(F)F)CC(C)(C)OC2=C1 OJBSBOPCVJQYHF-UHFFFAOYSA-N 0.000 description 1
- NXNMTDXMLILSIC-UHFFFAOYSA-N 2-[[4-(3-fluorophenyl)-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=CC=CC(F)=C1 NXNMTDXMLILSIC-UHFFFAOYSA-N 0.000 description 1
- KVZHKDQEOFITGU-UHFFFAOYSA-N 2-[[7,7-dimethyl-5-[3-(trifluoromethyl)phenyl]-6,8-dihydro-5H-naphthalen-2-yl]oxy]-N,N-dimethylethanamine Chemical compound CC1(CC(C2=CC=C(C=C2C1)OCCN(C)C)C1=CC(=CC=C1)C(F)(F)F)C KVZHKDQEOFITGU-UHFFFAOYSA-N 0.000 description 1
- REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 1
- NBBPBLQVQSJQGF-UHFFFAOYSA-N 2-ethyl-2-methyl-4-[3-(trifluoromethyl)phenyl]-3,4-dihydrochromen-7-ol Chemical compound C12=CC=C(O)C=C2OC(CC)(C)CC1C1=CC=CC(C(F)(F)F)=C1 NBBPBLQVQSJQGF-UHFFFAOYSA-N 0.000 description 1
- PIIBUNGEFZHCRH-UHFFFAOYSA-N 2-ethyl-7-hydroxy-2-methyl-3h-chromen-4-one Chemical compound C1=C(O)C=C2OC(CC)(C)CC(=O)C2=C1 PIIBUNGEFZHCRH-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- 150000000463 2H-chromenes Chemical class 0.000 description 1
- OUTKAEVCBLAWDO-UHFFFAOYSA-N 2h-chromene;hydrochloride Chemical compound Cl.C1=CC=C2C=CCOC2=C1 OUTKAEVCBLAWDO-UHFFFAOYSA-N 0.000 description 1
- VMUXSMXIQBNMGZ-UHFFFAOYSA-N 3,4-dihydrocoumarin Chemical compound C1=CC=C2OC(=O)CCC2=C1 VMUXSMXIQBNMGZ-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- KKMZQOIASVGJQE-UHFFFAOYSA-N 3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CS1 KKMZQOIASVGJQE-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
- BEULGBFCPWXDMC-UHFFFAOYSA-N 4-(4-fluorophenyl)-7-methoxy-1,2-dihydronaphthalene Chemical compound FC1=CC=C(C=C1)C1=CCCC2=CC(=CC=C12)OC BEULGBFCPWXDMC-UHFFFAOYSA-N 0.000 description 1
- MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical class C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- BMCPHBWFKJTXEE-UHFFFAOYSA-N 6-hydroxy-3,3-dimethyl-2,4-dihydronaphthalen-1-one Chemical compound OC=1C=C2CC(CC(C2=CC1)=O)(C)C BMCPHBWFKJTXEE-UHFFFAOYSA-N 0.000 description 1
- MAWZPNZRPKDBQI-UHFFFAOYSA-N 6-methoxy-3,3-dimethyl-2,4-dihydronaphthalen-1-one Chemical compound O=C1CC(C)(C)CC2=CC(OC)=CC=C21 MAWZPNZRPKDBQI-UHFFFAOYSA-N 0.000 description 1
- GXVSQTNPLYRINO-UHFFFAOYSA-N 7-[2-[benzyl(methyl)amino]ethoxy]-2,2-dimethyl-3h-chromen-4-one Chemical compound C=1C=C2C(=O)CC(C)(C)OC2=CC=1OCCN(C)CC1=CC=CC=C1 GXVSQTNPLYRINO-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-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
- 238000003747 Grignard reaction Methods 0.000 description 1
- 239000007818 Grignard reagent Substances 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
- 241000699670 Mus sp. Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-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
- 241000700159 Rattus Species 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
- 241000607479 Yersinia pestis Species 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 239000002775 capsule Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- DMSHWWDRAYHEBS-UHFFFAOYSA-N dihydrocoumarin Natural products C1CC(=O)OC2=C1C=C(OC)C(OC)=C2 DMSHWWDRAYHEBS-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000006277 halobenzyl group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
- YSKGFIVUCRKPJH-UHFFFAOYSA-N n-benzyl-2-[2,2-dimethyl-4-[3-(trifluoromethyl)phenyl]chromen-7-yl]oxy-n-methylethanamine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1CN(C)CCOC(C=C1OC(C)(C)C=2)=CC=C1C=2C1=CC=CC(C(F)(F)F)=C1 YSKGFIVUCRKPJH-UHFFFAOYSA-N 0.000 description 1
- XULSCZPZVQIMFM-IPZQJPLYSA-N odevixibat Chemical compound C12=CC(SC)=C(OCC(=O)N[C@@H](C(=O)N[C@@H](CC)C(O)=O)C=3C=CC(O)=CC=3)C=C2S(=O)(=O)NC(CCCC)(CCCC)CN1C1=CC=CC=C1 XULSCZPZVQIMFM-IPZQJPLYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 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
- 230000007017 scission Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 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 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 238000005406 washing Methods 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
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
-
- 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
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (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 |
|---|---|---|---|
| GB33549/74A GB1486001A (en) | 1974-07-30 | 1974-07-30 | 7-aminoalkoxy substituted benzopyrans benzo thiopyrans and naphthalenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2533885A1 true DE2533885A1 (de) | 1976-02-19 |
Family
ID=10354390
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752533885 Withdrawn DE2533885A1 (de) | 1974-07-30 | 1975-07-29 | Chroman-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | USRE30739E (enExample) |
| JP (1) | JPS51125055A (enExample) |
| AR (1) | AR210500A1 (enExample) |
| AT (1) | AT345283B (enExample) |
| AU (1) | AU500006B2 (enExample) |
| BE (1) | BE831939A (enExample) |
| CA (1) | CA1077478A (enExample) |
| CH (3) | CH622789A5 (enExample) |
| DE (1) | DE2533885A1 (enExample) |
| DK (1) | DK344175A (enExample) |
| ES (1) | ES439856A1 (enExample) |
| FR (2) | FR2280368A1 (enExample) |
| GB (1) | GB1486001A (enExample) |
| IE (1) | IE41273B1 (enExample) |
| IL (1) | IL47826A (enExample) |
| SE (1) | SE420490B (enExample) |
| ZA (1) | ZA754821B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0072942A3 (en) * | 1981-08-20 | 1984-06-06 | Mitsubishi Chemical Industries Limited | Pharmaceutically active (3-aminopropoxy)-bibenzyl derivatives |
| EP0778271A3 (de) * | 1995-12-08 | 2000-03-22 | F. Hoffmann-La Roche Ag | Aminoalkyl-substituierte benzo-heterocyclische Verbindungen |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2408600A1 (fr) * | 1977-10-11 | 1979-06-08 | Beecham Group Ltd | Derives des chromanes et leur application therapeutique |
| FR2639227A1 (fr) * | 1988-11-23 | 1990-05-25 | Sanofi Sa | Utilisation de derives du chromane pour le traitement des etats depressifs |
| US5166367A (en) * | 1991-06-21 | 1992-11-24 | American Home Products Corporation | Antipsychotic benzodioxan derivatives |
| GB2271566A (en) * | 1992-10-14 | 1994-04-20 | Merck & Co Inc | HIV integrase inhibitors |
| US6017768A (en) * | 1994-05-06 | 2000-01-25 | Pharmacopeia, Inc. | Combinatorial dihydrobenzopyran library |
| EP2725026B1 (de) * | 2012-10-29 | 2017-09-06 | Symrise AG | Heterozyklische neoflavonoide mit geschmacksmaskierenden eigenschaften |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3476767A (en) * | 1965-10-11 | 1969-11-04 | Ciba Geigy Corp | 1,2-diaryl - 6 - tertiary amino lower-alkoxy-3,4-dihydro naphthalenes |
| GB1357633A (en) * | 1971-03-02 | 1974-06-26 | Beecham Group Ltd | Chromanone basic ether derivatives |
-
1974
- 1974-07-30 GB GB33549/74A patent/GB1486001A/en not_active Expired
-
1975
- 1975-07-23 IE IE1647/75A patent/IE41273B1/xx unknown
- 1975-07-23 SE SE7508414A patent/SE420490B/xx unknown
- 1975-07-28 ZA ZA00754821A patent/ZA754821B/xx unknown
- 1975-07-28 FR FR7523453A patent/FR2280368A1/fr active Granted
- 1975-07-28 AT AT582775A patent/AT345283B/de not_active IP Right Cessation
- 1975-07-28 IL IL47826A patent/IL47826A/xx unknown
- 1975-07-29 DK DK344175A patent/DK344175A/da not_active Application Discontinuation
- 1975-07-29 CA CA232,421A patent/CA1077478A/en not_active Expired
- 1975-07-29 DE DE19752533885 patent/DE2533885A1/de not_active Withdrawn
- 1975-07-30 AU AU83536/75A patent/AU500006B2/en not_active Ceased
- 1975-07-30 JP JP50092980A patent/JPS51125055A/ja active Pending
- 1975-07-30 CH CH997275A patent/CH622789A5/de not_active IP Right Cessation
- 1975-07-30 ES ES439856A patent/ES439856A1/es not_active Expired
- 1975-07-30 BE BE158788A patent/BE831939A/xx unknown
-
1976
- 1976-01-16 FR FR7601065A patent/FR2313025A1/fr active Granted
- 1976-06-28 AR AR263765A patent/AR210500A1/es active
-
1979
- 1979-05-14 US US06/038,737 patent/USRE30739E/en not_active Expired - Lifetime
- 1979-05-30 CH CH503879A patent/CH624111A5/de not_active IP Right Cessation
- 1979-05-30 CH CH503779A patent/CH624110A5/de not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0072942A3 (en) * | 1981-08-20 | 1984-06-06 | Mitsubishi Chemical Industries Limited | Pharmaceutically active (3-aminopropoxy)-bibenzyl derivatives |
| EP0778271A3 (de) * | 1995-12-08 | 2000-03-22 | F. Hoffmann-La Roche Ag | Aminoalkyl-substituierte benzo-heterocyclische Verbindungen |
Also Published As
| Publication number | Publication date |
|---|---|
| CH622789A5 (en) | 1981-04-30 |
| ZA754821B (en) | 1976-07-28 |
| FR2313025A1 (fr) | 1976-12-31 |
| IL47826A0 (en) | 1975-10-15 |
| IL47826A (en) | 1979-05-31 |
| AU500006B2 (en) | 1979-05-10 |
| FR2280368A1 (fr) | 1976-02-27 |
| CA1077478A (en) | 1980-05-13 |
| AR210500A1 (es) | 1977-08-15 |
| SE420490B (sv) | 1981-10-12 |
| FR2313025B1 (enExample) | 1979-10-05 |
| USRE30739E (en) | 1981-09-08 |
| CH624111A5 (en) | 1981-07-15 |
| IE41273L (en) | 1976-01-30 |
| BE831939A (fr) | 1976-01-30 |
| ES439856A1 (es) | 1977-06-16 |
| ATA582775A (de) | 1978-01-15 |
| SE7508414L (sv) | 1976-02-02 |
| CH624110A5 (en) | 1981-07-15 |
| IE41273B1 (en) | 1979-11-21 |
| GB1486001A (en) | 1977-09-14 |
| AT345283B (de) | 1978-09-11 |
| FR2280368B1 (enExample) | 1979-08-10 |
| AU8353675A (en) | 1977-02-03 |
| DK344175A (da) | 1976-01-31 |
| JPS51125055A (en) | 1976-11-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1643224C3 (de) | 1 -Phenyl-2-aminoäthanolderivate und deren Säureadditionssalze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2635276A1 (de) | Tetrahydroisochinolin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate | |
| DE69820102T2 (de) | Substituierte chromanderivate | |
| DE2624570A1 (de) | Mehrkernige verbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| EP0075207B1 (de) | Aminopropanolderivate von 2-Hydroxy-beta-phenyl-propiophenonen, Verfahren zu ihrer Herstellung und diese enthaltende therapeutische Mittel | |
| DE1620198C3 (de) | 5H-Benz eckige Klammer auf f eckige Klammer zu 2,5-oxazocine oder Benz eckige Klammer auf g eckige Klammer zu 2,6-oxazonine, ihre Salze und Arzneimittel | |
| DE2533885A1 (de) | Chroman-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate | |
| AT390054B (de) | Verfahren zur herstellung von neuen benzoylderivaten von aliphatischen carbonsaeuren | |
| DE1793383C3 (de) | 4-Cyan-4-phenyl-aminocyclohexane und deren wasserlösliche Salze, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel | |
| DE2044172B2 (de) | Pyrrolderivate, ein Verfahren zu ihrer Herstellung und Arzneimittel | |
| EP0303920B1 (de) | Neue Benzofuranderivate und diese enthaltende therapeutische Mittel | |
| EP0082461A2 (de) | Substituierte Phenoxyalkanolamine und Phenoxyalkanol-cycloalkylamine, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende pharmazeutische Zubereitungen und Zwischenprodukte | |
| CH619208A5 (enExample) | ||
| DE2835536A1 (de) | Verfahren zur erzielung eines antioestrogenen effekts bei warmbluetern, hierfuer geeignete zusammensetzungen und verbindungen sowie verfahren zur herstellung dieser verbindungen | |
| US4148909A (en) | Chromans to treat depression and reduce appetite | |
| CH624382A5 (enExample) | ||
| DE2747987C2 (enExample) | ||
| EP0037062B1 (de) | Substituierte 3-Aryl-2-cycloalken-1-one, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel | |
| EP0031910B1 (de) | Anilinderivate, diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung | |
| DE1922280A1 (de) | Tricyclische Verbindungen und Verfahren zu deren Herstellung | |
| DE2639291A1 (de) | Neue aryl-alkylamine | |
| DE2013668A1 (de) | Neue Oxazolidin-2-one, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE4112353A1 (de) | 1,3,4-trisubstituierte piperidin-derivate, ihre herstellung und verwendung | |
| DE1545714C (de) | 4 eckige Klammer auf 1 Benzylpipendyl (2) eckige Klammer zu 2,2 diphenyl 1,3 dioxolane und Verfahren zu ihrer Herstellung | |
| DE2032642C3 (de) | 1 -Phenyl-2-aminoäthanol-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: JUNG, E., DIPL.-CHEM. DR.PHIL. SCHIRDEWAHN, J., DI |
|
| 8130 | Withdrawal |