NO862279L - Nye derivater av 1,1,2,2-tetrametyl-1,2-bis-(2-fluor-4-hydroksy-fenyl)-etaner. - Google Patents
Nye derivater av 1,1,2,2-tetrametyl-1,2-bis-(2-fluor-4-hydroksy-fenyl)-etaner.Info
- Publication number
- NO862279L NO862279L NO862279A NO862279A NO862279L NO 862279 L NO862279 L NO 862279L NO 862279 A NO862279 A NO 862279A NO 862279 A NO862279 A NO 862279A NO 862279 L NO862279 L NO 862279L
- Authority
- NO
- Norway
- Prior art keywords
- group
- formula
- compounds
- compound
- hydrogen
- Prior art date
Links
- -1 2-FLUORO-4-HYDROXY-PHENYL Chemical class 0.000 title description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 229940126601 medicinal product Drugs 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 238000010790 dilution Methods 0.000 claims 1
- 239000012895 dilution Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 abstract description 10
- 125000002252 acyl group Chemical group 0.000 abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 5
- 206010060862 Prostate cancer Diseases 0.000 abstract description 4
- 201000001514 prostate carcinoma Diseases 0.000 abstract description 4
- 230000000259 anti-tumor effect Effects 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000003513 alkali Substances 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910001868 water Inorganic materials 0.000 description 8
- 125000005843 halogen group Chemical group 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 201000008275 breast carcinoma Diseases 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- IUTGISNYEDWTCS-UHFFFAOYSA-N 3-fluoro-4-[3-(2-fluoro-4-hydroxyphenyl)-2,3-dimethylbutan-2-yl]phenol Chemical compound C=1C=C(O)C=C(F)C=1C(C)(C)C(C)(C)C1=CC=C(O)C=C1F IUTGISNYEDWTCS-UHFFFAOYSA-N 0.000 description 5
- 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 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 230000010933 acylation Effects 0.000 description 5
- 238000005917 acylation reaction Methods 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
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- 238000001816 cooling Methods 0.000 description 5
- 230000001419 dependent effect Effects 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000375 suspending agent Substances 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VFZRZRDOXPRTSC-UHFFFAOYSA-N DMBA Natural products COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000001833 anti-estrogenic effect Effects 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000328 estrogen antagonist Substances 0.000 description 4
- 229940088597 hormone Drugs 0.000 description 4
- 239000005556 hormone Substances 0.000 description 4
- 150000004678 hydrides Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229940046836 anti-estrogen Drugs 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 102000015694 estrogen receptors Human genes 0.000 description 3
- 108010038795 estrogen receptors Proteins 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RNCUHIILUNOEGW-UHFFFAOYSA-N 2-(2-fluoro-4-methoxyphenyl)propan-2-ol Chemical compound COC1=CC=C(C(C)(C)O)C(F)=C1 RNCUHIILUNOEGW-UHFFFAOYSA-N 0.000 description 2
- BDWVXXSVUXFIIW-UHFFFAOYSA-N 2-fluoro-1-[3-(2-fluoro-4-methoxyphenyl)-2,3-dimethylbutan-2-yl]-4-methoxybenzene Chemical compound FC1=CC(OC)=CC=C1C(C)(C)C(C)(C)C1=CC=C(OC)C=C1F BDWVXXSVUXFIIW-UHFFFAOYSA-N 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 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 2
- 241001465754 Metazoa Species 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- DYGWVFAVZJGSNB-UHFFFAOYSA-N [4-[3-(4-carbamoyloxy-2-fluorophenyl)-2,3-dimethylbutan-2-yl]-3-fluorophenyl] carbamate Chemical compound C=1C=C(OC(N)=O)C=C(F)C=1C(C)(C)C(C)(C)C1=CC=C(OC(N)=O)C=C1F DYGWVFAVZJGSNB-UHFFFAOYSA-N 0.000 description 2
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- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
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- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000012453 sprague-dawley rat model Methods 0.000 description 2
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- RQHMQURGSQBBJY-UHFFFAOYSA-N (2,2-dichloroacetyl) 2,2-dichloroacetate Chemical compound ClC(Cl)C(=O)OC(=O)C(Cl)Cl RQHMQURGSQBBJY-UHFFFAOYSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
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- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
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- VXTPSLDGPFDDHR-UHFFFAOYSA-N [4-[3-(4-acetyloxy-2-fluorophenyl)-2,3-dimethylbutan-2-yl]-3-fluorophenyl] acetate Chemical compound FC1=CC(OC(=O)C)=CC=C1C(C)(C)C(C)(C)C1=CC=C(OC(C)=O)C=C1F VXTPSLDGPFDDHR-UHFFFAOYSA-N 0.000 description 1
- LCCUSOAFUPEPRM-UHFFFAOYSA-N [4-[3-[4-(2,2-dichloroacetyl)oxy-2-fluorophenyl]-2,3-dimethylbutan-2-yl]-3-fluorophenyl] 2,2-dichloroacetate Chemical compound C=1C=C(OC(=O)C(Cl)Cl)C=C(F)C=1C(C)(C)C(C)(C)C1=CC=C(OC(=O)C(Cl)Cl)C=C1F LCCUSOAFUPEPRM-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
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- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- RDXABLXNTVBVML-UHFFFAOYSA-N diethoxyphosphanyl diethyl phosphite Chemical compound CCOP(OCC)OP(OCC)OCC RDXABLXNTVBVML-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- UZZWBUYVTBPQIV-UHFFFAOYSA-N dme dimethoxyethane Chemical compound COCCOC.COCCOC UZZWBUYVTBPQIV-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 201000003914 endometrial carcinoma Diseases 0.000 description 1
- 229960005309 estradiol Drugs 0.000 description 1
- 229930182833 estradiol Natural products 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 230000001076 estrogenic effect Effects 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000000659 freezing mixture Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006578 reductive coupling reaction Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229960003604 testosterone Drugs 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- NRTLTGGGUQIRRT-UHFFFAOYSA-N triethylazanium;bromide Chemical compound [Br-].CC[NH+](CC)CC NRTLTGGGUQIRRT-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/367—Halogenated derivatives polycyclic non-condensed, containing only six-membered aromatic rings as cyclic parts, e.g. halogenated poly-hydroxyphenylalkanes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3520622 | 1985-06-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO862279D0 NO862279D0 (no) | 1986-06-06 |
| NO862279L true NO862279L (no) | 1986-12-09 |
Family
ID=6272805
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO862279A NO862279L (no) | 1985-06-08 | 1986-06-06 | Nye derivater av 1,1,2,2-tetrametyl-1,2-bis-(2-fluor-4-hydroksy-fenyl)-etaner. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4745233A (fi) |
| EP (1) | EP0206021B1 (fi) |
| JP (1) | JPS6242953A (fi) |
| AT (1) | ATE36312T1 (fi) |
| AU (1) | AU5847386A (fi) |
| CA (1) | CA1273953A (fi) |
| DD (1) | DD260490A5 (fi) |
| DE (1) | DE3660489D1 (fi) |
| DK (1) | DK268386A (fi) |
| ES (1) | ES8705357A1 (fi) |
| FI (1) | FI862431A (fi) |
| GR (1) | GR861480B (fi) |
| HU (1) | HUT43552A (fi) |
| IL (1) | IL79055A0 (fi) |
| NO (1) | NO862279L (fi) |
| PT (1) | PT82726B (fi) |
| SU (1) | SU1676459A3 (fi) |
| YU (1) | YU95986A (fi) |
| ZA (1) | ZA864262B (fi) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01155753A (ja) * | 1987-12-11 | 1989-06-19 | Nippon Telegr & Teleph Corp <Ntt> | 留守番電話機 |
| EP1289519B1 (en) * | 2000-05-26 | 2019-02-13 | Harry Fisch | Methods of treating androgen deficiency in men using clomiphene |
| CA2453337C (en) | 2001-07-09 | 2012-08-28 | Zonagen, Inc. | Methods and materials for the treatment of testosterone deficiency in men |
| US7737185B2 (en) | 2001-07-09 | 2010-06-15 | Repros Therapeutics Inc. | Methods and compositions with trans-clomiphene |
| BRPI0609389A2 (pt) | 2005-03-22 | 2010-03-30 | Repros Therapeutics Inc | tablete, composição e respectivos usos |
| UA96076C2 (en) | 2007-10-16 | 2011-09-26 | Репрос Терапьютикс Инк. | Use of trans-clomiphene |
| UA113291C2 (xx) | 2011-08-04 | 2017-01-10 | Метаболіти транскломіфену і їх застосування | |
| US9687458B2 (en) | 2012-11-02 | 2017-06-27 | Repros Therapeutics Inc. | Trans-clomiphene for use in cancer therapy |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2021588B (en) * | 1978-04-05 | 1983-03-30 | Biorex Laboratories Ltd | Bibenzyl derivatives the preparation thereof and pharmaceutical compositions containing them |
| DE2927050A1 (de) * | 1979-07-04 | 1981-01-15 | Biorex Laboratories Ltd | Bibenzylderivate |
| US4427697A (en) * | 1980-11-18 | 1984-01-24 | Biorex Laboratories Limited | 1,2-Diphenylethane derivatives |
| US4467121A (en) * | 1980-12-31 | 1984-08-21 | General Electric Company | Fluorinated diphenols and method for their preparation |
-
1986
- 1986-06-04 DE DE8686107568T patent/DE3660489D1/de not_active Expired
- 1986-06-04 EP EP86107568A patent/EP0206021B1/de not_active Expired
- 1986-06-04 AT AT86107568T patent/ATE36312T1/de not_active IP Right Cessation
- 1986-06-05 YU YU00959/86A patent/YU95986A/xx unknown
- 1986-06-06 ES ES555785A patent/ES8705357A1/es not_active Expired
- 1986-06-06 DD DD86291079A patent/DD260490A5/de unknown
- 1986-06-06 GR GR861480A patent/GR861480B/el unknown
- 1986-06-06 ZA ZA864262A patent/ZA864262B/xx unknown
- 1986-06-06 JP JP61130455A patent/JPS6242953A/ja active Pending
- 1986-06-06 CA CA000511010A patent/CA1273953A/en not_active Expired - Lifetime
- 1986-06-06 DK DK268386A patent/DK268386A/da not_active Application Discontinuation
- 1986-06-06 AU AU58473/86A patent/AU5847386A/en not_active Abandoned
- 1986-06-06 HU HU862404A patent/HUT43552A/hu unknown
- 1986-06-06 FI FI862431A patent/FI862431A/fi not_active IP Right Cessation
- 1986-06-06 PT PT82726A patent/PT82726B/pt not_active IP Right Cessation
- 1986-06-06 IL IL79055A patent/IL79055A0/xx unknown
- 1986-06-06 NO NO862279A patent/NO862279L/no unknown
- 1986-06-09 US US06/871,892 patent/US4745233A/en not_active Expired - Fee Related
-
1987
- 1987-02-06 SU SU874028942A patent/SU1676459A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6242953A (ja) | 1987-02-24 |
| HUT43552A (en) | 1987-11-30 |
| IL79055A0 (en) | 1986-09-30 |
| PT82726B (pt) | 1988-12-15 |
| FI862431A (fi) | 1986-12-09 |
| EP0206021A1 (de) | 1986-12-30 |
| AU5847386A (en) | 1986-12-11 |
| PT82726A (de) | 1986-07-01 |
| FI862431A0 (fi) | 1986-06-06 |
| NO862279D0 (no) | 1986-06-06 |
| YU95986A (en) | 1988-02-29 |
| ES555785A0 (es) | 1987-05-01 |
| ATE36312T1 (de) | 1988-08-15 |
| DK268386A (da) | 1986-12-09 |
| DE3660489D1 (en) | 1988-09-15 |
| ES8705357A1 (es) | 1987-05-01 |
| DK268386D0 (da) | 1986-06-06 |
| GR861480B (en) | 1986-10-07 |
| EP0206021B1 (de) | 1988-08-10 |
| ZA864262B (en) | 1987-02-25 |
| CA1273953A (en) | 1990-09-11 |
| US4745233A (en) | 1988-05-17 |
| DD260490A5 (de) | 1988-09-28 |
| SU1676459A3 (ru) | 1991-09-07 |
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