SE450250B - Nya 1,1,2-trifenylpropan-och-propenderivat, sett for deras framstellning och farmaceutiska beredningar innehallande dem - Google Patents
Nya 1,1,2-trifenylpropan-och-propenderivat, sett for deras framstellning och farmaceutiska beredningar innehallande demInfo
- Publication number
- SE450250B SE450250B SE8005688A SE8005688A SE450250B SE 450250 B SE450250 B SE 450250B SE 8005688 A SE8005688 A SE 8005688A SE 8005688 A SE8005688 A SE 8005688A SE 450250 B SE450250 B SE 450250B
- Authority
- SE
- Sweden
- Prior art keywords
- group
- phenyl
- general formula
- trifluoro
- compound
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 67
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 128
- 229910052739 hydrogen Inorganic materials 0.000 claims description 128
- 239000000203 mixture Substances 0.000 claims description 117
- -1 methoxy-methoxy Chemical group 0.000 claims description 96
- 229910052757 nitrogen Inorganic materials 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 20
- 239000000460 chlorine Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 12
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 150000007514 bases Chemical class 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 9
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 9
- 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 9
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 8
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- UVGJVHUDMMBHRM-UHFFFAOYSA-N 1,1,2-Triphenylpropane Chemical compound C=1C=CC=CC=1C(C)C(C=1C=CC=CC=1)C1=CC=CC=C1 UVGJVHUDMMBHRM-UHFFFAOYSA-N 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical class CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 238000005661 deetherification reaction Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000005335 azido alkyl group Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 123
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 121
- 229910052731 fluorine Inorganic materials 0.000 description 107
- 238000004458 analytical method Methods 0.000 description 106
- 229910052799 carbon Inorganic materials 0.000 description 101
- 239000000243 solution Substances 0.000 description 96
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 90
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- 239000000047 product Substances 0.000 description 75
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 70
- 238000002844 melting Methods 0.000 description 70
- 230000008018 melting Effects 0.000 description 70
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 28
- 239000000499 gel Substances 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
- 239000007858 starting material Substances 0.000 description 21
- 238000000034 method Methods 0.000 description 17
- 238000001704 evaporation Methods 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 16
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- 239000012043 crude product Substances 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 12
- SFAOEAYQPFKFRE-FMQUCBEESA-N 4-[(e)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]phenol Chemical compound C1=CC(O)=CC=C1C(\C=1C=CC=CC=1)=C(C(F)(F)F)/C1=CC=CC=C1 SFAOEAYQPFKFRE-FMQUCBEESA-N 0.000 description 11
- 206010028980 Neoplasm Diseases 0.000 description 11
- 238000009835 boiling Methods 0.000 description 11
- 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 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 description 10
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- BRCGOGKJLHHRDS-QURGRASLSA-N 1-(2-bromoethoxy)-4-[(e)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]benzene Chemical group C=1C=CC=CC=1/C(C(F)(F)F)=C(C=1C=CC(OCCBr)=CC=1)/C1=CC=CC=C1 BRCGOGKJLHHRDS-QURGRASLSA-N 0.000 description 9
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 238000010171 animal model Methods 0.000 description 8
- 125000006016 2-bromoethoxy group Chemical group 0.000 description 7
- 101100441092 Danio rerio crlf3 gene Proteins 0.000 description 7
- 102000009151 Luteinizing Hormone Human genes 0.000 description 7
- 108010073521 Luteinizing Hormone Proteins 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 229940040129 luteinizing hormone Drugs 0.000 description 7
- 239000012452 mother liquor Substances 0.000 description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 6
- ARSRBNBHOADGJU-UHFFFAOYSA-N 7,12-dimethyltetraphene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C)=C(C=CC=C1)C1=C2C ARSRBNBHOADGJU-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000001294 propane Substances 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 239000012261 resinous substance Substances 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229960001603 tamoxifen Drugs 0.000 description 5
- VFZRZRDOXPRTSC-UHFFFAOYSA-N DMBA Natural products COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- HRQGCQVOJVTVLU-UHFFFAOYSA-N bis(chloromethyl) ether Chemical compound ClCOCCl HRQGCQVOJVTVLU-UHFFFAOYSA-N 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- BYKATOOZEOHCIQ-UHFFFAOYSA-N 1-fluoro-4-[3,3,3-trifluoro-1,2-bis(4-methoxyphenyl)prop-1-enyl]benzene Chemical group C1=CC(OC)=CC=C1C(C=1C=CC(F)=CC=1)=C(C(F)(F)F)C1=CC=C(OC)C=C1 BYKATOOZEOHCIQ-UHFFFAOYSA-N 0.000 description 3
- BACVWORDWWQYGD-UHFFFAOYSA-N 1-fluoro-4-[3,3,3-trifluoro-1-(4-methoxyphenyl)-2-phenylpropyl]benzene Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(F)=CC=1)C(C(F)(F)F)C1=CC=CC=C1 BACVWORDWWQYGD-UHFFFAOYSA-N 0.000 description 3
- VDANWWLAEZSDEU-UHFFFAOYSA-N 1-fluoro-4-[3,3,3-trifluoro-2-(4-methoxyphenyl)-1-phenylprop-1-enyl]benzene Chemical compound C1=CC(OC)=CC=C1C(C(F)(F)F)=C(C=1C=CC(F)=CC=1)C1=CC=CC=C1 VDANWWLAEZSDEU-UHFFFAOYSA-N 0.000 description 3
- VJGVEHOZSWTFCV-QURGRASLSA-N 2-[4-[(e)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]phenoxy]ethanamine Chemical group C1=CC(OCCN)=CC=C1C(\C=1C=CC=CC=1)=C(C(F)(F)F)/C1=CC=CC=C1 VJGVEHOZSWTFCV-QURGRASLSA-N 0.000 description 3
- CXSJUKLCVLLACK-UHFFFAOYSA-N 4-[3,3,3-trifluoro-1-(4-fluorophenyl)-2-phenylpropyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(F)=CC=1)C(C(F)(F)F)C1=CC=CC=C1 CXSJUKLCVLLACK-UHFFFAOYSA-N 0.000 description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 3
- 208000026310 Breast neoplasm Diseases 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000001833 anti-estrogenic effect Effects 0.000 description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000328 estrogen antagonist Substances 0.000 description 3
- 230000001076 estrogenic effect Effects 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- VUXPBJNOQSAYCC-UHFFFAOYSA-N n,n-dimethyl-2-[4-[3,3,3-trifluoro-2-phenyl-1-(4-phenylmethoxyphenyl)prop-1-enyl]phenoxy]ethanamine Chemical group C1=CC(OCCN(C)C)=CC=C1C(C=1C=CC(OCC=2C=CC=CC=2)=CC=1)=C(C(F)(F)F)C1=CC=CC=C1 VUXPBJNOQSAYCC-UHFFFAOYSA-N 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 230000001836 utereotrophic effect Effects 0.000 description 3
- CBHDAHHYMRXLIP-UHFFFAOYSA-M (4-fluorophenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].C1=CC(F)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CBHDAHHYMRXLIP-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BRCGOGKJLHHRDS-DQRAZIAOSA-N 1-(2-bromoethoxy)-4-[(z)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]benzene Chemical group C=1C=CC=CC=1/C(C(F)(F)F)=C(C=1C=CC(OCCBr)=CC=1)\C1=CC=CC=C1 BRCGOGKJLHHRDS-DQRAZIAOSA-N 0.000 description 2
- SHQPQWDRGVNWJZ-UHFFFAOYSA-N 1-[3-bromo-1,1,1-trifluoro-3-(4-fluorophenyl)propan-2-yl]-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1C(C(F)(F)F)C(Br)C1=CC=C(F)C=C1 SHQPQWDRGVNWJZ-UHFFFAOYSA-N 0.000 description 2
- CFGFVCRICOEJSC-UHFFFAOYSA-N 1-fluoro-4-[3,3,3-trifluoro-1-(4-methoxyphenyl)-2-phenylprop-1-enyl]benzene Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(F)=CC=1)=C(C(F)(F)F)C1=CC=CC=C1 CFGFVCRICOEJSC-UHFFFAOYSA-N 0.000 description 2
- AAEZWDFUXYFSLS-UHFFFAOYSA-N 1-fluoro-4-[3,3,3-trifluoro-2-(4-methoxyphenyl)-1-phenylpropyl]benzene Chemical compound C1=CC(OC)=CC=C1C(C(F)(F)F)C(C=1C=CC(F)=CC=1)C1=CC=CC=C1 AAEZWDFUXYFSLS-UHFFFAOYSA-N 0.000 description 2
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 2
- KZJRKRQSDZGHEC-UHFFFAOYSA-N 2,2,2-trifluoro-1-phenylethanone Chemical compound FC(F)(F)C(=O)C1=CC=CC=C1 KZJRKRQSDZGHEC-UHFFFAOYSA-N 0.000 description 2
- 229940087189 2,2,2-trifluoroacetophenone Drugs 0.000 description 2
- CFAFEJHONLMPQY-UHFFFAOYSA-N 2-(dimethylazaniumyl)ethanesulfonate Chemical compound CN(C)CCS(O)(=O)=O CFAFEJHONLMPQY-UHFFFAOYSA-N 0.000 description 2
- MHXVDXXARZCVRK-WCWDXBQESA-N 2-[2-[4-[(e)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]phenoxy]ethylamino]ethanol Chemical compound C1=CC(OCCNCCO)=CC=C1C(\C=1C=CC=CC=1)=C(C(F)(F)F)/C1=CC=CC=C1 MHXVDXXARZCVRK-WCWDXBQESA-N 0.000 description 2
- QZBSWHQXYVYKBH-UHFFFAOYSA-N 4-[2-(4-chlorophenyl)-3,3,3-trifluoro-1-phenylpropyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC=CC=1)C(C(F)(F)F)C1=CC=C(Cl)C=C1 QZBSWHQXYVYKBH-UHFFFAOYSA-N 0.000 description 2
- FQEZUJYENUITNB-OCEACIFDSA-N 4-[2-[4-[(e)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]phenoxy]ethyl]morpholine Chemical compound C=1C=CC=CC=1/C(C(F)(F)F)=C(C=1C=CC(OCCN2CCOCC2)=CC=1)/C1=CC=CC=C1 FQEZUJYENUITNB-OCEACIFDSA-N 0.000 description 2
- AUXAVMQTOZMWTG-UHFFFAOYSA-N 4-[2-[4-[3,3,3-trifluoro-1-[4-(methoxymethoxy)phenyl]-2-phenylprop-1-enyl]phenoxy]ethyl]morpholine Chemical compound C1=CC(OCOC)=CC=C1C(C=1C=CC(OCCN2CCOCC2)=CC=1)=C(C(F)(F)F)C1=CC=CC=C1 AUXAVMQTOZMWTG-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 206010006187 Breast cancer Diseases 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 235000019759 Maize starch Nutrition 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 210000000750 endocrine system Anatomy 0.000 description 2
- 229960005309 estradiol Drugs 0.000 description 2
- 229930182833 estradiol Natural products 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- IESSOWYGECYNGF-UHFFFAOYSA-N n-methyl-2-[4-[3,3,3-trifluoro-1-[4-(methoxymethoxy)phenyl]-2-phenylprop-1-enyl]phenoxy]ethanamine Chemical compound C1=CC(OCCNC)=CC=C1C(C=1C=CC(OCOC)=CC=1)=C(C(F)(F)F)C1=CC=CC=C1 IESSOWYGECYNGF-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 210000002381 plasma Anatomy 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 210000004291 uterus Anatomy 0.000 description 2
- BZLSCVAPEFKLSB-UHFFFAOYSA-N (1,1,1-trifluoro-2-phenylpropan-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C(F)(F)F)(C)C1=CC=CC=C1 BZLSCVAPEFKLSB-UHFFFAOYSA-N 0.000 description 1
- VQQBQTCNLRMSKY-UHFFFAOYSA-N (1,1,1-trifluoro-3-phenylpropan-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C(F)(F)F)CC1=CC=CC=C1 VQQBQTCNLRMSKY-UHFFFAOYSA-N 0.000 description 1
- RTSUHIVNLKAOKO-UHFFFAOYSA-N (3,3,3-trifluoro-1-phenylprop-1-en-2-yl)benzene Chemical group C=1C=CC=CC=1C(C(F)(F)F)=CC1=CC=CC=C1 RTSUHIVNLKAOKO-UHFFFAOYSA-N 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- 229940005561 1,4-benzoquinone Drugs 0.000 description 1
- LDECJCHQNOJURM-UHFFFAOYSA-N 1-(1-bromo-3,3,3-trifluoro-2-phenylpropyl)-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1C(Br)C(C(F)(F)F)C1=CC=CC=C1 LDECJCHQNOJURM-UHFFFAOYSA-N 0.000 description 1
- RKXXDPOIOWRHNT-QURGRASLSA-N 1-(2-azidoethoxy)-4-[(e)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]benzene Chemical group C=1C=CC=CC=1/C(C(F)(F)F)=C(C=1C=CC(OCCN=[N+]=[N-])=CC=1)/C1=CC=CC=C1 RKXXDPOIOWRHNT-QURGRASLSA-N 0.000 description 1
- WRNCYMIXRZYIJU-UHFFFAOYSA-N 1-(2-azidoethoxy)-4-[3,3,3-trifluoro-2-(4-fluorophenyl)-1-phenylprop-1-enyl]benzene Chemical compound C1=CC(F)=CC=C1C(C(F)(F)F)=C(C=1C=CC(OCCN=[N+]=[N-])=CC=1)C1=CC=CC=C1 WRNCYMIXRZYIJU-UHFFFAOYSA-N 0.000 description 1
- ZDTOXWBPTYMOGR-UHFFFAOYSA-N 1-(2-bromoethoxy)-4-[3,3,3-trifluoro-1-(4-fluorophenyl)-2-phenylprop-1-enyl]benzene Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(OCCBr)=CC=1)=C(C(F)(F)F)C1=CC=CC=C1 ZDTOXWBPTYMOGR-UHFFFAOYSA-N 0.000 description 1
- XARMJGRAZKMKBU-UHFFFAOYSA-N 1-(2-bromoethoxy)-4-[3,3,3-trifluoro-2-(4-fluorophenyl)-1-phenylprop-1-enyl]benzene Chemical group C1=CC(F)=CC=C1C(C(F)(F)F)=C(C=1C=CC(OCCBr)=CC=1)C1=CC=CC=C1 XARMJGRAZKMKBU-UHFFFAOYSA-N 0.000 description 1
- FHDYRFNCTJFNQX-UHFFFAOYSA-N 1-(2-chloroethyl)-4-methylpiperazine Chemical compound CN1CCN(CCCl)CC1 FHDYRFNCTJFNQX-UHFFFAOYSA-N 0.000 description 1
- RMGFLMXDCGQKPS-UHFFFAOYSA-N 1-(2-chloroethyl)pyrrolidine Chemical compound ClCCN1CCCC1 RMGFLMXDCGQKPS-UHFFFAOYSA-N 0.000 description 1
- OCKXVEYJKZHKLT-UHFFFAOYSA-N 1-(3-bromo-1,1,1-trifluoro-3-phenylpropan-2-yl)-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1C(C(F)(F)F)C(Br)C1=CC=CC=C1 OCKXVEYJKZHKLT-UHFFFAOYSA-N 0.000 description 1
- DYPQUENOGZXOGE-UHFFFAOYSA-N 1-(4-chlorophenyl)-2,2,2-trifluoroethanone Chemical compound FC(F)(F)C(=O)C1=CC=C(Cl)C=C1 DYPQUENOGZXOGE-UHFFFAOYSA-N 0.000 description 1
- OOELKUNWFXFKAD-UHFFFAOYSA-N 1-(methoxymethoxy)-4-prop-1-enylbenzene Chemical compound COCOC1=CC=C(C=CC)C=C1 OOELKUNWFXFKAD-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- QMBCBSQHCXGXCM-OCEACIFDSA-N 1-[2-[4-[(e)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]phenoxy]ethyl]pyrrolidine Chemical compound C=1C=CC=CC=1/C(C(F)(F)F)=C(C=1C=CC(OCCN2CCCC2)=CC=1)/C1=CC=CC=C1 QMBCBSQHCXGXCM-OCEACIFDSA-N 0.000 description 1
- BQGMEHFJNDYZLG-UHFFFAOYSA-N 1-chloro-4-(1,1,1-trifluoro-3-phenylpropan-2-yl)benzene Chemical compound C=1C=C(Cl)C=CC=1C(C(F)(F)F)CC1=CC=CC=C1 BQGMEHFJNDYZLG-UHFFFAOYSA-N 0.000 description 1
- UQQQRJZRRMOOPO-UHFFFAOYSA-N 1-chloro-4-(3,3,3-trifluoro-1-phenylprop-1-en-2-yl)benzene Chemical group C=1C=C(Cl)C=CC=1C(C(F)(F)F)=CC1=CC=CC=C1 UQQQRJZRRMOOPO-UHFFFAOYSA-N 0.000 description 1
- XEYIQUKYKYRQCR-UHFFFAOYSA-N 1-chloro-4-[1,1,1-trifluoro-3-(4-methoxyphenyl)-3-phenylpropan-2-yl]benzene Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC=CC=1)C(C(F)(F)F)C1=CC=C(Cl)C=C1 XEYIQUKYKYRQCR-UHFFFAOYSA-N 0.000 description 1
- QPWGGIPIVVOZOE-UHFFFAOYSA-N 1-fluoro-4-(1,1,1-trifluoro-3-phenylpropan-2-yl)benzene Chemical compound C1=CC(F)=CC=C1C(C(F)(F)F)CC1=CC=CC=C1 QPWGGIPIVVOZOE-UHFFFAOYSA-N 0.000 description 1
- XCYDVXGAQPYGJG-UHFFFAOYSA-N 1-fluoro-4-(3,3,3-trifluoro-2-phenylprop-1-enyl)benzene Chemical group C1=CC(F)=CC=C1C=C(C(F)(F)F)C1=CC=CC=C1 XCYDVXGAQPYGJG-UHFFFAOYSA-N 0.000 description 1
- XKGCOZOMRXODOF-UHFFFAOYSA-N 1-fluoro-4-(3,3,3-trifluoro-2-phenylpropyl)benzene Chemical compound C1=CC(F)=CC=C1CC(C(F)(F)F)C1=CC=CC=C1 XKGCOZOMRXODOF-UHFFFAOYSA-N 0.000 description 1
- CNYKYXANFLSTCU-VXPUYCOJSA-N 1-fluoro-4-[(z)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]benzene Chemical group C1=CC(F)=CC=C1C(\C=1C=CC=CC=1)=C(C(F)(F)F)\C1=CC=CC=C1 CNYKYXANFLSTCU-VXPUYCOJSA-N 0.000 description 1
- KDCPHMMIAJWHSV-UHFFFAOYSA-N 1-fluoro-4-[1,1,1-trifluoro-3-(4-methoxyphenyl)-3-phenylpropan-2-yl]benzene Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC=CC=1)C(C(F)(F)F)C1=CC=C(F)C=C1 KDCPHMMIAJWHSV-UHFFFAOYSA-N 0.000 description 1
- CWYBAFLCKCFIDG-UHFFFAOYSA-N 1-fluoro-4-[3,3,3-trifluoro-1,2-bis(4-methoxyphenyl)propyl]benzene Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(F)=CC=1)C(C(F)(F)F)C1=CC=C(OC)C=C1 CWYBAFLCKCFIDG-UHFFFAOYSA-N 0.000 description 1
- QHXLOGCPLXWLFP-UHFFFAOYSA-N 1-fluoro-4-[3,3,3-trifluoro-1,2-bis[4-(methoxymethoxy)phenyl]prop-1-enyl]benzene Chemical compound FC1=CC=C(C=C1)C(=C(C(F)(F)F)C1=CC=C(C=C1)OCOC)C1=CC=C(C=C1)OCOC QHXLOGCPLXWLFP-UHFFFAOYSA-N 0.000 description 1
- SBQYMRUYWPHDQY-UHFFFAOYSA-N 1-fluoro-4-[3,3,3-trifluoro-1-[4-(methoxymethoxy)phenyl]-2-phenylprop-1-enyl]benzene Chemical group C1=CC(OCOC)=CC=C1C(C=1C=CC(F)=CC=1)=C(C(F)(F)F)C1=CC=CC=C1 SBQYMRUYWPHDQY-UHFFFAOYSA-N 0.000 description 1
- UUSNOKKYMDRDKA-UHFFFAOYSA-N 1-fluoro-4-[3,3,3-trifluoro-1-[4-(methoxymethoxy)phenyl]-2-phenylpropyl]benzene Chemical compound C1=CC(OCOC)=CC=C1C(C=1C=CC(F)=CC=1)C(C(F)(F)F)C1=CC=CC=C1 UUSNOKKYMDRDKA-UHFFFAOYSA-N 0.000 description 1
- DZJFECRVYIBCNU-UHFFFAOYSA-N 1-fluoro-4-[3,3,3-trifluoro-2-(4-methoxyphenyl)prop-1-enyl]benzene Chemical compound C1=CC(OC)=CC=C1C(C(F)(F)F)=CC1=CC=C(F)C=C1 DZJFECRVYIBCNU-UHFFFAOYSA-N 0.000 description 1
- UHHDYKSJEMUQIQ-UHFFFAOYSA-N 1-fluoro-4-[3,3,3-trifluoro-2-(4-methoxyphenyl)propyl]benzene Chemical compound C1=CC(OC)=CC=C1C(C(F)(F)F)CC1=CC=C(F)C=C1 UHHDYKSJEMUQIQ-UHFFFAOYSA-N 0.000 description 1
- YLOIIRKIMWNQGE-UHFFFAOYSA-N 1-fluoro-4-[3,3,3-trifluoro-2-[4-(methoxymethoxy)phenyl]-1-phenylprop-1-enyl]benzene Chemical compound C1(=CC=CC=C1)C(=C(C(F)(F)F)C1=CC=C(C=C1)OCOC)C1=CC=C(C=C1)F YLOIIRKIMWNQGE-UHFFFAOYSA-N 0.000 description 1
- DAKDWUJZQTVHNO-UHFFFAOYSA-N 1-fluoro-4-[3,3,3-trifluoro-2-[4-(methoxymethoxy)phenyl]-1-phenylpropyl]benzene Chemical compound C1=CC(OCOC)=CC=C1C(C(F)(F)F)C(C=1C=CC(F)=CC=1)C1=CC=CC=C1 DAKDWUJZQTVHNO-UHFFFAOYSA-N 0.000 description 1
- RQQGFXQENHKJLU-UHFFFAOYSA-N 1-fluoro-4-[3,3,3-trifluoro-2-phenyl-1-(4-phenylmethoxyphenyl)prop-1-enyl]benzene Chemical group C(C1=CC=CC=C1)OC1=CC=C(C=C1)C(=C(C(F)(F)F)C1=CC=CC=C1)C1=CC=C(C=C1)F RQQGFXQENHKJLU-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- SMILDTCRTVKJRM-UHFFFAOYSA-N 1-methoxy-4-(3,3,3-trifluoroprop-1-enyl)benzene Chemical group COC1=CC=C(C=CC(F)(F)F)C=C1 SMILDTCRTVKJRM-UHFFFAOYSA-N 0.000 description 1
- UHKDEXCHHRFEIA-QURGRASLSA-N 1-nitro-2-[2-[4-[(e)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]phenoxy]ethyl]guanidine Chemical compound C1=CC(OCCN=C(N[N+]([O-])=O)N)=CC=C1C(\C=1C=CC=CC=1)=C(C(F)(F)F)/C1=CC=CC=C1 UHKDEXCHHRFEIA-QURGRASLSA-N 0.000 description 1
- FWFSVRAOFAWTBN-CYYJNZCTSA-N 1-phenylmethoxy-4-[(e)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]benzene Chemical group C=1C=CC=CC=1/C(C(F)(F)F)=C(C=1C=CC(OCC=2C=CC=CC=2)=CC=1)/C1=CC=CC=C1 FWFSVRAOFAWTBN-CYYJNZCTSA-N 0.000 description 1
- LUKLMXJAEKXROG-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-fluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)C(F)(F)F)C=C1 LUKLMXJAEKXROG-UHFFFAOYSA-N 0.000 description 1
- NCJZVRPXSSYDBG-UHFFFAOYSA-N 2,2,2-trifluoro-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)C(F)(F)F)C=C1 NCJZVRPXSSYDBG-UHFFFAOYSA-N 0.000 description 1
- HCTVOEJAGPGJMS-UHFFFAOYSA-N 2,4-dimethoxy-1-(3,3,3-trifluoroprop-1-enyl)benzene Chemical group COC1=CC(=C(C=C1)C=CC(F)(F)F)OC HCTVOEJAGPGJMS-UHFFFAOYSA-N 0.000 description 1
- 125000000586 2-(4-morpholinyl)ethoxy group Chemical group [H]C([H])(O*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
- KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical compound OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 description 1
- VJPLIVYQOFNXNF-OCEACIFDSA-N 2-[2-hydroxyethyl-[2-[4-[(e)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]phenoxy]ethyl]amino]ethanol Chemical group C1=CC(OCCN(CCO)CCO)=CC=C1C(\C=1C=CC=CC=1)=C(C(F)(F)F)/C1=CC=CC=C1 VJPLIVYQOFNXNF-OCEACIFDSA-N 0.000 description 1
- PAPFKQMLZNVGIM-UHFFFAOYSA-N 2-[4-[3,3,3-trifluoro-2-(4-fluorophenyl)-1-phenylprop-1-enyl]phenoxy]ethanamine Chemical compound C1=CC(OCCN)=CC=C1C(C=1C=CC=CC=1)=C(C(F)(F)F)C1=CC=C(F)C=C1 PAPFKQMLZNVGIM-UHFFFAOYSA-N 0.000 description 1
- SYOITAKYEVGUCF-GHVJWSGMSA-N 2-[[4-[(e)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]phenoxy]methyl]oxirane Chemical group C=1C=CC=CC=1/C(C(F)(F)F)=C(C=1C=CC(OCC2OC2)=CC=1)/C1=CC=CC=C1 SYOITAKYEVGUCF-GHVJWSGMSA-N 0.000 description 1
- NXFMZCXQGYAODD-UHFFFAOYSA-N 2-[[4-[2-(4-chlorophenyl)-3,3,3-trifluoro-1-phenylpropyl]phenoxy]methyl]oxirane Chemical compound C=1C=C(Cl)C=CC=1C(C(F)(F)F)C(C=1C=CC(OCC2OC2)=CC=1)C1=CC=CC=C1 NXFMZCXQGYAODD-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- OVHZLCNZAYAVFH-UHFFFAOYSA-N 3-(4-chlorophenyl)-8-[[cyclohexyl(ethyl)azaniumyl]methyl]-4-oxo-2-(trifluoromethyl)chromen-7-olate Chemical compound C1CCCCC1N(CC)CC1=C(O)C=CC(C2=O)=C1OC(C(F)(F)F)=C2C1=CC=C(Cl)C=C1 OVHZLCNZAYAVFH-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZAPMTSHEXFEPSD-UHFFFAOYSA-N 4-(2-chloroethyl)morpholine Chemical compound ClCCN1CCOCC1 ZAPMTSHEXFEPSD-UHFFFAOYSA-N 0.000 description 1
- WIQVHKYWMPIUPL-QZQOTICOSA-N 4-[(e)-3,3,3-trifluoro-1-(4-methoxyphenyl)-2-phenylprop-1-enyl]phenol Chemical group C1=CC(OC)=CC=C1C(\C=1C=CC(O)=CC=1)=C(C(F)(F)F)/C1=CC=CC=C1 WIQVHKYWMPIUPL-QZQOTICOSA-N 0.000 description 1
- SFAOEAYQPFKFRE-VXPUYCOJSA-N 4-[(z)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]phenol Chemical compound C1=CC(O)=CC=C1C(\C=1C=CC=CC=1)=C(C(F)(F)F)\C1=CC=CC=C1 SFAOEAYQPFKFRE-VXPUYCOJSA-N 0.000 description 1
- LJKZTGWVFITPBB-UHFFFAOYSA-N 4-[1,1,1-trifluoro-3-(4-fluorophenyl)-3-phenylpropan-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)C(C=1C=CC(F)=CC=1)C1=CC=CC=C1 LJKZTGWVFITPBB-UHFFFAOYSA-N 0.000 description 1
- WXLHNNXCLHXNJJ-UHFFFAOYSA-N 4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-3,3,3-trifluoro-1-phenylprop-1-en-2-yl]phenol;hydrochloride Chemical compound Cl.C1=CC(OCCN(C)C)=CC=C1C(C=1C=CC=CC=1)=C(C(F)(F)F)C1=CC=C(O)C=C1 WXLHNNXCLHXNJJ-UHFFFAOYSA-N 0.000 description 1
- SLBPTGDZITTZRH-UHFFFAOYSA-N 4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-3,3,3-trifluoro-2-(4-hydroxyphenyl)prop-1-enyl]phenol Chemical compound C1=CC(OCCN(C)C)=CC=C1C(C=1C=CC(O)=CC=1)=C(C(F)(F)F)C1=CC=C(O)C=C1 SLBPTGDZITTZRH-UHFFFAOYSA-N 0.000 description 1
- JDCBOQULKZIXDQ-UHFFFAOYSA-N 4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-3,3,3-trifluoro-2-(4-hydroxyphenyl)prop-1-enyl]phenol;hydrochloride Chemical compound Cl.C1=CC(OCCN(C)C)=CC=C1C(C=1C=CC(O)=CC=1)=C(C(F)(F)F)C1=CC=C(O)C=C1 JDCBOQULKZIXDQ-UHFFFAOYSA-N 0.000 description 1
- ICAWOROTCPABQF-UHFFFAOYSA-N 4-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-3,3,3-trifluoro-2-phenylprop-1-enyl]phenol Chemical group C1=CC(OCCN(C)C)=CC=C1C(C=1C=CC(O)=CC=1)=C(C(F)(F)F)C1=CC=CC=C1 ICAWOROTCPABQF-UHFFFAOYSA-N 0.000 description 1
- HDPHDNLOVIMODX-UHFFFAOYSA-N 4-[2-[4-[3,3,3-trifluoro-1-(4-fluorophenyl)-2-phenylprop-1-enyl]phenoxy]ethyl]morpholine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(OCCN2CCOCC2)=CC=1)=C(C(F)(F)F)C1=CC=CC=C1 HDPHDNLOVIMODX-UHFFFAOYSA-N 0.000 description 1
- UYRHFIGOKINGNL-UHFFFAOYSA-N 4-[3,3,3-trifluoro-1-(4-fluorophenyl)-2-(4-hydroxyphenyl)propyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(F)=CC=1)C(C(F)(F)F)C1=CC=C(O)C=C1 UYRHFIGOKINGNL-UHFFFAOYSA-N 0.000 description 1
- VODMBSIHCSMJQR-UHFFFAOYSA-N 4-[3,3,3-trifluoro-1-[4-(2-morpholin-4-ylethoxy)phenyl]-2-phenylprop-1-enyl]phenol Chemical group C1=CC(O)=CC=C1C(C=1C=CC(OCCN2CCOCC2)=CC=1)=C(C(F)(F)F)C1=CC=CC=C1 VODMBSIHCSMJQR-UHFFFAOYSA-N 0.000 description 1
- JHSCBGJTVFMDQQ-UHFFFAOYSA-N 4-[3,3,3-trifluoro-1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenylprop-1-enyl]phenol;hydrochloride Chemical compound Cl.C1=CC(OCCNC)=CC=C1C(C=1C=CC(O)=CC=1)=C(C(F)(F)F)C1=CC=CC=C1 JHSCBGJTVFMDQQ-UHFFFAOYSA-N 0.000 description 1
- VSCBKIDBBWINHA-UHFFFAOYSA-N 4-[3,3,3-trifluoro-2-(4-fluorophenyl)-1-phenylpropyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC=CC=1)C(C(F)(F)F)C1=CC=C(F)C=C1 VSCBKIDBBWINHA-UHFFFAOYSA-N 0.000 description 1
- GTXCDTSRYQBWTC-QUABFQRHSA-N 4-methylbenzenesulfonic acid;2-[4-[(e)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]phenoxy]ethanamine Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.C1=CC(OCCN)=CC=C1C(\C=1C=CC=CC=1)=C(C(F)(F)F)/C1=CC=CC=C1 GTXCDTSRYQBWTC-QUABFQRHSA-N 0.000 description 1
- MWJDNCANDJACFK-RXQWRGDBSA-N 4-methylbenzenesulfonic acid;n-[2-[4-[(e)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]phenoxy]ethyl]hexan-1-amine Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.C1=CC(OCCNCCCCCC)=CC=C1C(\C=1C=CC=CC=1)=C(C(F)(F)F)/C1=CC=CC=C1 MWJDNCANDJACFK-RXQWRGDBSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 1
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
- BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 description 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 206010067572 Oestrogenic effect Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 101001109716 Rhizobium meliloti (strain 1021) NAD(P)H dehydrogenase (quinone) 3 Proteins 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000282485 Vulpes vulpes Species 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229960003608 clomifene Drugs 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical class C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940113088 dimethylacetamide Drugs 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 229960002568 ethinylestradiol Drugs 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- BHCHMKIUFDXIGK-BTKVJIOYSA-N n,n-diethyl-2-[4-[(e)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]phenoxy]ethanamine;2,4,6-trinitrophenol Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O.C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(C(F)(F)F)/C1=CC=CC=C1 BHCHMKIUFDXIGK-BTKVJIOYSA-N 0.000 description 1
- WNCNUKOFVFRDCT-WCWDXBQESA-N n,n-dimethyl-2-[4-[(e)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]phenoxy]ethanamine Chemical group C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(C(F)(F)F)/C1=CC=CC=C1 WNCNUKOFVFRDCT-WCWDXBQESA-N 0.000 description 1
- JWYHVPQNHSQJEJ-XMXXDQCKSA-N n,n-dimethyl-2-[4-[(e)-3,3,3-trifluoro-1,2-diphenylprop-1-enyl]phenoxy]ethanamine;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC(OCCN(C)C)=CC=C1C(\C=1C=CC=CC=1)=C(C(F)(F)F)/C1=CC=CC=C1 JWYHVPQNHSQJEJ-XMXXDQCKSA-N 0.000 description 1
- YOIJUNCHTLOCFA-UHFFFAOYSA-N n,n-dimethyl-2-[4-[3,3,3-trifluoro-1,2-bis(4-methoxyphenyl)prop-1-enyl]phenoxy]ethanamine Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(OCCN(C)C)=CC=1)=C(C(F)(F)F)C1=CC=C(OC)C=C1 YOIJUNCHTLOCFA-UHFFFAOYSA-N 0.000 description 1
- ZOMLVQJMPDARHL-UHFFFAOYSA-N n,n-dimethyl-2-[4-[3,3,3-trifluoro-1,2-bis[4-(methoxymethoxy)phenyl]prop-1-enyl]phenoxy]ethanamine Chemical group C1=CC(OCOC)=CC=C1C(C=1C=CC(OCCN(C)C)=CC=1)=C(C(F)(F)F)C1=CC=C(OCOC)C=C1 ZOMLVQJMPDARHL-UHFFFAOYSA-N 0.000 description 1
- FCQIHSVBRSIHSE-UHFFFAOYSA-N n,n-dimethyl-2-[4-[3,3,3-trifluoro-2-(4-methoxyphenyl)-1-phenylprop-1-enyl]phenoxy]ethanamine Chemical group C1=CC(OC)=CC=C1C(C(F)(F)F)=C(C=1C=CC(OCCN(C)C)=CC=1)C1=CC=CC=C1 FCQIHSVBRSIHSE-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
- 239000000376 reactant Substances 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
- 230000028327 secretion Effects 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 230000001875 tumorinhibitory effect Effects 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/2635—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions involving a phosphorus compound, e.g. Wittig synthesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/14—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the side-chain of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
-
- 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
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/18—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/20—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
-
- 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
- C07C37/001—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain
- C07C37/003—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by modification in a side chain by hydrogenation of an unsaturated part
-
- 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
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- 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
- C07D295/08—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 bound oxygen or sulfur atoms
- C07D295/084—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B63—SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
- B63B—SHIPS OR OTHER WATERBORNE VESSELS; EQUIPMENT FOR SHIPPING
- B63B22/00—Buoys
- B63B2022/006—Buoys specially adapted for measuring or watch purposes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B63—SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
- B63B—SHIPS OR OTHER WATERBORNE VESSELS; EQUIPMENT FOR SHIPPING
- B63B2211/00—Applications
- B63B2211/02—Oceanography
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Endocrinology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Reproductive Health (AREA)
- Diabetes (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79GO1455A HU178253B (en) | 1979-08-15 | 1979-08-15 | Process for preparing 1,1,2-triphenyl-propane and -propane derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE8005688L SE8005688L (sv) | 1981-02-16 |
| SE450250B true SE450250B (sv) | 1987-06-15 |
Family
ID=10996899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8005688A SE450250B (sv) | 1979-08-15 | 1980-08-12 | Nya 1,1,2-trifenylpropan-och-propenderivat, sett for deras framstellning och farmaceutiska beredningar innehallande dem |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5668637A (cs) |
| AT (1) | AT372074B (cs) |
| BE (1) | BE884716A (cs) |
| BG (3) | BG35031A3 (cs) |
| CA (1) | CA1179359A (cs) |
| CH (1) | CH649758A5 (cs) |
| CS (1) | CS241030B2 (cs) |
| DD (1) | DD152536A5 (cs) |
| DE (1) | DE3030802A1 (cs) |
| DK (1) | DK351780A (cs) |
| ES (1) | ES494286A0 (cs) |
| FI (1) | FI74271C (cs) |
| FR (1) | FR2463121B1 (cs) |
| GB (1) | GB2058061B (cs) |
| GR (1) | GR69821B (cs) |
| HU (1) | HU178253B (cs) |
| IT (1) | IT1228130B (cs) |
| NL (1) | NL8004542A (cs) |
| PL (3) | PL131226B1 (cs) |
| SE (1) | SE450250B (cs) |
| SU (3) | SU1253426A1 (cs) |
| YU (2) | YU42980B (cs) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0175188A1 (de) * | 1984-09-11 | 1986-03-26 | Nihon Tokushu Noyaku Seizo K.K. | Carbamoylimidazol-Derivate |
| US5681835A (en) * | 1994-04-25 | 1997-10-28 | Glaxo Wellcome Inc. | Non-steroidal ligands for the estrogen receptor |
| AU3879095A (en) * | 1994-11-02 | 1996-05-31 | Egis Gyogyszergyar Rt. | Process and intermediates for preparing triphenyltrifluoropropanes and -propenes |
| HUP0002852A3 (en) | 1997-08-15 | 2001-11-28 | Univ Durham | A method of preventing or treating estrogen-dependent diseases and disorders using triphenil-ethylene derivatives |
| CN1061334C (zh) * | 1998-06-02 | 2001-01-31 | 中国科学院上海有机化学研究所 | 不饱和键三氟乙基化化合物的制备方法 |
| US7935697B2 (en) * | 2006-12-28 | 2011-05-03 | Kinex Pharmaceuticals, Llc | Compositions for modulating a kinase cascade and methods of use thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE637389A (cs) * | 1962-09-13 | |||
| US3712929A (en) * | 1969-10-31 | 1973-01-23 | Du Pont | 1-perfluoroalkyl-1,2,2-triphenylethylenes |
-
1979
- 1979-08-15 HU HU79GO1455A patent/HU178253B/hu not_active IP Right Cessation
-
1980
- 1980-08-11 BE BE1/9927A patent/BE884716A/fr not_active IP Right Cessation
- 1980-08-11 NL NL8004542A patent/NL8004542A/nl not_active Application Discontinuation
- 1980-08-12 GR GR62652A patent/GR69821B/el unknown
- 1980-08-12 FR FR8017735A patent/FR2463121B1/fr not_active Expired
- 1980-08-12 SE SE8005688A patent/SE450250B/sv not_active IP Right Cessation
- 1980-08-14 IT IT8024152A patent/IT1228130B/it active
- 1980-08-14 BG BG052061A patent/BG35031A3/xx unknown
- 1980-08-14 BG BG052060A patent/BG35032A3/xx unknown
- 1980-08-14 CH CH6129/80A patent/CH649758A5/de not_active IP Right Cessation
- 1980-08-14 DE DE19803030802 patent/DE3030802A1/de active Granted
- 1980-08-14 BG BG048852A patent/BG34903A3/xx unknown
- 1980-08-14 CS CS805616A patent/CS241030B2/cs unknown
- 1980-08-14 ES ES494286A patent/ES494286A0/es active Granted
- 1980-08-14 DK DK351780A patent/DK351780A/da not_active Application Discontinuation
- 1980-08-14 AT AT0419280A patent/AT372074B/de not_active IP Right Cessation
- 1980-08-14 DD DD80223329A patent/DD152536A5/de not_active IP Right Cessation
- 1980-08-15 GB GB8026768A patent/GB2058061B/en not_active Expired
- 1980-08-15 PL PL1980238084A patent/PL131226B1/pl unknown
- 1980-08-15 FI FI802584A patent/FI74271C/fi not_active IP Right Cessation
- 1980-08-15 PL PL1980238085A patent/PL131227B1/pl unknown
- 1980-08-15 CA CA000358369A patent/CA1179359A/en not_active Expired
- 1980-08-15 SU SU802968606A patent/SU1253426A1/ru active
- 1980-08-15 JP JP11260780A patent/JPS5668637A/ja active Granted
- 1980-08-15 YU YU2068/80A patent/YU42980B/xx unknown
- 1980-08-16 PL PL1980226254A patent/PL130386B1/pl unknown
-
1981
- 1981-10-16 SU SU813344199A patent/SU1114332A3/ru active
- 1981-10-16 SU SU813344743A patent/SU1097192A3/ru active
-
1983
- 1983-06-03 YU YU1239/83A patent/YU43182B/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0005142A1 (de) | Phenylpiperazinderivate, Verfahren zu ihrer Herstellung, Zwischenprodukte hierfür und Arzneimittel enthaltend solche Phenylpiperazinderivate | |
| SE445640B (sv) | Imidazolderivat, forfarande for framstellning derav samt farmaceutiska kompositioner derav | |
| DE69208551T2 (de) | Benzo(a)fluorenverbindungen | |
| US4304721A (en) | Adrenergic blocking agents | |
| US4806685A (en) | 1,1,2-triphenylpropane and -propene derivatives | |
| FR2463122A1 (fr) | Amides polyprenylcarboxyliques, procede de preparation de ceux-ci et composition pharmaceutique a base desdits amides | |
| US4556677A (en) | Alkane and alkene derivatives and their use | |
| US4247710A (en) | Intermediate in the production of adrenergic blocking agents | |
| GB2058061A (en) | 1,1,2-Triphenylpropane and -propene derivatives | |
| US4329289A (en) | Adrenergic blocking agents | |
| NZ191916A (en) | 1,1,2-triphenylalkene derivatives and pharmaceutical compositions | |
| US4285873A (en) | Adrenergic blocking agents | |
| US4281189A (en) | Sulfonamide intermediates for adrenergic blocking agents | |
| US4278608A (en) | Adrenergic blocking agents | |
| WO1982000141A1 (en) | 3-amino-propoxy-phenyl derivatives,preparation thereof and drugs containing them | |
| DE2754029C2 (de) | ω-Aminoalkoxybenzol-Derivate, deren Herstellung und Verwendung | |
| FR2505655A1 (fr) | Medicaments constitues par de nouveaux aminoderives en position 1 du 1-(3',4'-methylenedioxyphenyl)propan-2-ol et leur procede de fabrication | |
| US4659833A (en) | Optically active isocarbostyril derivatives and a method of preparing the same | |
| US4336382A (en) | 1,4-Disubstituted piperazine compounds | |
| JPH0353314B2 (cs) | ||
| US4503075A (en) | Derivatives of 1-alkylamine-3[4(p-alkyloxy-benzamide)phenoxy]-2-propanol, having beta-sympatholytic activity, their salts, and production processes thereof | |
| KR840002089B1 (ko) | 치환된 펜옥시-아미노프로판올 유도체의 제조방법 | |
| US4314085A (en) | Intermediates for preparing adrenergic blocking agents | |
| AU633261B2 (en) | Antiinflammatory carbinoloimidazoles | |
| CS247575B1 (cs) | Deriváty 1-fenoxy-3-fenoxyethylamino-2-propanolu a způsob jejich přípravy |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAL | Patent in force |
Ref document number: 8005688-0 Format of ref document f/p: F |
|
| NUG | Patent has lapsed |
Ref document number: 8005688-0 Format of ref document f/p: F |