DE2514809A1 - Substituierte triphenylaethylene, verfahren zu ihrer herstellung und sie enthaltende arzneimittel - Google Patents
Substituierte triphenylaethylene, verfahren zu ihrer herstellung und sie enthaltende arzneimittelInfo
- Publication number
- DE2514809A1 DE2514809A1 DE19752514809 DE2514809A DE2514809A1 DE 2514809 A1 DE2514809 A1 DE 2514809A1 DE 19752514809 DE19752514809 DE 19752514809 DE 2514809 A DE2514809 A DE 2514809A DE 2514809 A1 DE2514809 A1 DE 2514809A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- formula
- compound
- carbon atoms
- methanesulfonanilide
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229940126601 medicinal product Drugs 0.000 title 1
- -1 α-chloro-β-phenylstyryl Chemical group 0.000 claims description 68
- 150000001875 compounds Chemical class 0.000 claims description 64
- 239000000047 product Substances 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 238000006297 dehydration reaction Methods 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
- 230000018044 dehydration Effects 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
- 239000000243 solution Substances 0.000 description 35
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 22
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- LBTPIFQNEKOAIM-UHFFFAOYSA-N n-phenylmethanesulfonamide Chemical class CS(=O)(=O)NC1=CC=CC=C1 LBTPIFQNEKOAIM-UHFFFAOYSA-N 0.000 description 18
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N N,N-Diethylethanamine Substances CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- MKYQPGPNVYRMHI-UHFFFAOYSA-N Triphenylethylene Chemical class C=1C=CC=CC=1C=C(C=1C=CC=CC=1)C1=CC=CC=C1 MKYQPGPNVYRMHI-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000003509 anti-fertility effect Effects 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 230000001076 estrogenic effect Effects 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 229940086542 triethylamine Drugs 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000003776 cleavage reaction Methods 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride 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
- OHBTULDTCSOWOY-UHFFFAOYSA-N [C].C=C Chemical group [C].C=C OHBTULDTCSOWOY-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 230000007017 scission Effects 0.000 description 5
- HXKPUARSGIFGQU-UHFFFAOYSA-N 1-(1-bromopropyl)-4-methoxybenzene Chemical compound CCC(Br)C1=CC=C(OC)C=C1 HXKPUARSGIFGQU-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000699666 Mus <mouse, genus> Species 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 150000001860 citric acid derivatives Chemical class 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 125000005322 morpholin-1-yl group Chemical group 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 4
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 3
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- 229910010082 LiAlH Inorganic materials 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 206010067572 Oestrogenic effect Diseases 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000005122 aminoalkylamino group Chemical group 0.000 description 3
- 239000012965 benzophenone Substances 0.000 description 3
- 125000002837 carbocyclic group Chemical group 0.000 description 3
- 150000001722 carbon compounds Chemical class 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000000262 estrogen Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- FVWVXLPJUYNZLL-UHFFFAOYSA-N n-(4-benzoylphenyl)methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(=O)C1=CC=CC=C1 FVWVXLPJUYNZLL-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- OAWJISLDPLWHLQ-UHFFFAOYSA-N n-phenylbutane-1-sulfonamide Chemical compound CCCCS(=O)(=O)NC1=CC=CC=C1 OAWJISLDPLWHLQ-UHFFFAOYSA-N 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 230000001836 utereotrophic effect Effects 0.000 description 3
- 210000004291 uterus Anatomy 0.000 description 3
- QMPKJVBRCQVFLL-UHFFFAOYSA-N 1,1,2-triphenylethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)CC1=CC=CC=C1 QMPKJVBRCQVFLL-UHFFFAOYSA-N 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- SKRFPQORFROXTP-UHFFFAOYSA-N 2-oxo-n,2-diphenylethanesulfonamide Chemical compound C=1C=CC=CC=1C(=O)CS(=O)(=O)NC1=CC=CC=C1 SKRFPQORFROXTP-UHFFFAOYSA-N 0.000 description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- 206010012373 Depressed level of consciousness Diseases 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- 125000002431 aminoalkoxy group Chemical group 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000001833 anti-estrogenic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 239000003433 contraceptive agent Substances 0.000 description 2
- 230000006003 cornification Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910003480 inorganic solid Inorganic materials 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- GDRRXTCEIGOOCZ-UHFFFAOYSA-N n-(3-benzoylphenyl)-n-[2-(diethylamino)ethyl]methanesulfonamide Chemical compound CCN(CC)CCN(S(C)(=O)=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 GDRRXTCEIGOOCZ-UHFFFAOYSA-N 0.000 description 2
- FBYZMZOTNKLBRL-UHFFFAOYSA-N n-(4-benzoylphenyl)-n-[2-(diethylamino)ethyl]methanesulfonamide Chemical compound C1=CC(N(CCN(CC)CC)S(C)(=O)=O)=CC=C1C(=O)C1=CC=CC=C1 FBYZMZOTNKLBRL-UHFFFAOYSA-N 0.000 description 2
- YPJAFEKEOIXZLW-UHFFFAOYSA-N n-(4-benzoylphenyl)butane-1-sulfonamide Chemical compound C1=CC(NS(=O)(=O)CCCC)=CC=C1C(=O)C1=CC=CC=C1 YPJAFEKEOIXZLW-UHFFFAOYSA-N 0.000 description 2
- NYNXRTRNYULVNX-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-n-[4-(2-phenylbutanoyl)phenyl]methanesulfonamide Chemical compound C=1C=CC=CC=1C(CC)C(=O)C1=CC=C(N(CCN(CC)CC)S(C)(=O)=O)C=C1 NYNXRTRNYULVNX-UHFFFAOYSA-N 0.000 description 2
- IGCVCLCQYWQFQB-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-n-[4-(3-methoxybenzoyl)phenyl]methanesulfonamide Chemical compound C1=CC(N(CCN(CC)CC)S(C)(=O)=O)=CC=C1C(=O)C1=CC=CC(OC)=C1 IGCVCLCQYWQFQB-UHFFFAOYSA-N 0.000 description 2
- NLKCFMIBBKAJNS-UHFFFAOYSA-N n-[4-(2-methoxybenzoyl)phenyl]methanesulfonamide Chemical compound COC1=CC=CC=C1C(=O)C1=CC=C(NS(C)(=O)=O)C=C1 NLKCFMIBBKAJNS-UHFFFAOYSA-N 0.000 description 2
- NHEDSBDOSXNUKU-UHFFFAOYSA-N n-[4-(3-methoxybenzoyl)phenyl]methanesulfonamide Chemical compound COC1=CC=CC(C(=O)C=2C=CC(NS(C)(=O)=O)=CC=2)=C1 NHEDSBDOSXNUKU-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- FUADXEJBHCKVBN-UHFFFAOYSA-N (3-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 FUADXEJBHCKVBN-UHFFFAOYSA-N 0.000 description 1
- BDSVOVBZCXYQBU-UHFFFAOYSA-N (4-aminophenyl)-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)C=2C=CC(N)=CC=2)=C1 BDSVOVBZCXYQBU-UHFFFAOYSA-N 0.000 description 1
- RBKHNGHPZZZJCI-UHFFFAOYSA-N (4-aminophenyl)-phenylmethanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 RBKHNGHPZZZJCI-UHFFFAOYSA-N 0.000 description 1
- MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical class C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- ZZEPPWLXZLMJOL-UHFFFAOYSA-N 1-(2-chloroethyl)azocane Chemical compound ClCCN1CCCCCCC1 ZZEPPWLXZLMJOL-UHFFFAOYSA-N 0.000 description 1
- WNRWEBKEQARBKV-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine Chemical compound ClCCN1CCCCC1 WNRWEBKEQARBKV-UHFFFAOYSA-N 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45793274A | 1974-04-04 | 1974-04-04 | |
| US05/457,931 US4001229A (en) | 1974-04-04 | 1974-04-04 | Alkanesulfonamido triphenylethylenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2514809A1 true DE2514809A1 (de) | 1975-10-16 |
Family
ID=27038784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752514809 Pending DE2514809A1 (de) | 1974-04-04 | 1975-04-04 | Substituierte triphenylaethylene, verfahren zu ihrer herstellung und sie enthaltende arzneimittel |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS50137965A (en, 2012) |
| CH (1) | CH614192A5 (en, 2012) |
| DE (1) | DE2514809A1 (en, 2012) |
| DK (1) | DK135375A (en, 2012) |
| FR (2) | FR2266494B1 (en, 2012) |
| GB (1) | GB1481648A (en, 2012) |
| IE (1) | IE40905B1 (en, 2012) |
| LU (1) | LU72188A1 (en, 2012) |
| NL (1) | NL7503855A (en, 2012) |
| SE (1) | SE418179B (en, 2012) |
| YU (1) | YU71175A (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4572884A (en) * | 1982-11-25 | 1986-02-25 | Ricoh Company, Ltd. | Stilbene derivatives and electrophotographic photoconductor comprising one stilbene derivative |
-
1975
- 1975-03-24 YU YU00711/75A patent/YU71175A/xx unknown
- 1975-03-26 DK DK135375A patent/DK135375A/da unknown
- 1975-03-28 FR FR7509807A patent/FR2266494B1/fr not_active Expired
- 1975-04-01 NL NL7503855A patent/NL7503855A/xx not_active Application Discontinuation
- 1975-04-01 SE SE7503725A patent/SE418179B/xx unknown
- 1975-04-02 LU LU72188A patent/LU72188A1/xx unknown
- 1975-04-03 GB GB13684/75A patent/GB1481648A/en not_active Expired
- 1975-04-03 IE IE743/75A patent/IE40905B1/xx unknown
- 1975-04-03 JP JP50039876A patent/JPS50137965A/ja active Pending
- 1975-04-04 DE DE19752514809 patent/DE2514809A1/de active Pending
- 1975-04-04 CH CH430375A patent/CH614192A5/xx not_active IP Right Cessation
-
1978
- 1978-08-31 FR FR7825227A patent/FR2391724A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SE418179B (sv) | 1981-05-11 |
| IE40905B1 (en) | 1979-09-12 |
| SE7503725L (sv) | 1975-10-06 |
| AU7892475A (en) | 1976-09-16 |
| IE40905L (en) | 1975-10-04 |
| FR2266494B1 (en, 2012) | 1980-02-08 |
| NL7503855A (nl) | 1975-10-07 |
| DK135375A (en, 2012) | 1975-10-05 |
| YU71175A (en) | 1982-06-18 |
| FR2391724B1 (en, 2012) | 1981-12-04 |
| LU72188A1 (en, 2012) | 1976-03-02 |
| FR2391724A1 (fr) | 1978-12-22 |
| CH614192A5 (en) | 1979-11-15 |
| FR2266494A1 (en, 2012) | 1975-10-31 |
| GB1481648A (en) | 1977-08-03 |
| JPS50137965A (en, 2012) | 1975-11-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |