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
Authority: NO; Norway
Prior art keywords: group; formula; compounds; compound; hydrogen
Prior art date: 1985-06-08

Application number

NO862279A

Other languages

English (en)

Norwegian (no)

Other versions

NO862279D0 (no

Inventor

Helmut Schoenenberger

Rolf W Hartmann

Martin Schneider

Walter Schwarz

Juergen Engel

Original Assignee

Asta Pharma Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-06-08

Filing date

1986-06-06

Publication date

1986-12-09

1986-06-06 Application filed by Asta Pharma Ag filed Critical Asta Pharma Ag

1986-06-06 Publication of NO862279D0 publication Critical patent/NO862279D0/no

1986-12-09 Publication of NO862279L publication Critical patent/NO862279L/no

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
239000003795 chemical substances by application Substances 0.000 description 5
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
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 2
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
229910001854 alkali hydroxide Inorganic materials 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
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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PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
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230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
238000005661 deetherification reaction Methods 0.000 description 2
235000019700 dicalcium phosphate Nutrition 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
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235000011852 gelatine desserts Nutrition 0.000 description 2
239000008187 granular material Substances 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
230000000366 juvenile effect Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000002674 ointment Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
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
MJOXZELXZLIYPI-UHFFFAOYSA-N titanium(2+) Chemical compound [Ti+2] MJOXZELXZLIYPI-UHFFFAOYSA-N 0.000 description 2
239000008215 water for injection Substances 0.000 description 2
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
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
PIRRWUMTIBFCCW-UHFFFAOYSA-N 1-(2-fluoro-4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(C)=O)C(F)=C1 PIRRWUMTIBFCCW-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
NXTLHAJDCMVQFB-UHFFFAOYSA-N 4-[3-(4-hydroxyphenyl)-2,3-dimethylbutan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(C)C(C)(C)C1=CC=C(O)C=C1 NXTLHAJDCMVQFB-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
230000004913 activation Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
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239000000443 aerosol Substances 0.000 description 1
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)
Compositions Of Macromolecular Compounds (AREA)
Polyesters Or Polycarbonates (AREA)
Hydrogenated Pyridines (AREA)
Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)

NO862279A 1985-06-08 1986-06-06 Nye derivater av 1,1,2,2-tetrametyl-1,2-bis-(2-fluor-4-hydroksy-fenyl)-etaner. NO862279L (no)

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 (pt)
EP (1)	EP0206021B1 (pt)
JP (1)	JPS6242953A (pt)
AT (1)	ATE36312T1 (pt)
AU (1)	AU5847386A (pt)
CA (1)	CA1273953A (pt)
DD (1)	DD260490A5 (pt)
DE (1)	DE3660489D1 (pt)
DK (1)	DK268386A (pt)
ES (1)	ES8705357A1 (pt)
FI (1)	FI862431A (pt)
GR (1)	GR861480B (pt)
HU (1)	HUT43552A (pt)
IL (1)	IL79055A0 (pt)
NO (1)	NO862279L (pt)
PT (1)	PT82726B (pt)
SU (1)	SU1676459A3 (pt)
YU (1)	YU95986A (pt)
ZA (1)	ZA864262B (pt)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
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
WO2001091744A1 (en) *	2000-05-26	2001-12-06	Harry Fisch	Methods of treating androgen deficiency in men using selective antiestrogens
PT1411916E (pt)	2001-07-09	2008-12-10	Repros Therapeutics Inc	Métodos e materiais para o tratamento de deficiência em testosterona nos homens
US7737185B2 (en)	2001-07-09	2010-06-15	Repros Therapeutics Inc.	Methods and compositions with trans-clomiphene
PL383444A1 (pl)	2005-03-22	2008-03-17	Repros Therapeutics Inc.	Sposoby dawkowania trans-klomifenu
ES2718912T3 (es)	2007-10-16	2019-07-05	Repros Therapeutics Inc	Trans-clomifeno para el tratamiento de la diabetes en hombres hipogonadales
UA113291C2 (xx)	2011-08-04	2017-01-10		Метаболіти транскломіфену і їх застосування
CN104994877A (zh)	2012-11-02	2015-10-21	利普生物药剂公司	用于癌症治疗的反式-克罗米芬

Family Cites Families (4)

* Cited by examiner, † Cited by third party
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 FI FI862431A patent/FI862431A/fi not_active IP Right Cessation
- 1986-06-06 CA CA000511010A patent/CA1273953A/en not_active Expired - Lifetime
- 1986-06-06 NO NO862279A patent/NO862279L/no unknown
- 1986-06-06 DD DD86291079A patent/DD260490A5/de unknown
- 1986-06-06 HU HU862404A patent/HUT43552A/hu unknown
- 1986-06-06 DK DK268386A patent/DK268386A/da not_active Application Discontinuation
- 1986-06-06 PT PT82726A patent/PT82726B/pt not_active IP Right Cessation
- 1986-06-06 GR GR861480A patent/GR861480B/el unknown
- 1986-06-06 IL IL79055A patent/IL79055A0/xx unknown
- 1986-06-06 JP JP61130455A patent/JPS6242953A/ja active Pending
- 1986-06-06 AU AU58473/86A patent/AU5847386A/en not_active Abandoned
- 1986-06-06 ES ES555785A patent/ES8705357A1/es not_active Expired
- 1986-06-06 ZA ZA864262A patent/ZA864262B/xx 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
ATE36312T1 (de)	1988-08-15
CA1273953A (en)	1990-09-11
YU95986A (en)	1988-02-29
DD260490A5 (de)	1988-09-28
ES555785A0 (es)	1987-05-01
DE3660489D1 (en)	1988-09-15
US4745233A (en)	1988-05-17
DK268386A (da)	1986-12-09
GR861480B (en)	1986-10-07
FI862431A0 (fi)	1986-06-06
SU1676459A3 (ru)	1991-09-07
HUT43552A (en)	1987-11-30
IL79055A0 (en)	1986-09-30
JPS6242953A (ja)	1987-02-24
AU5847386A (en)	1986-12-11
NO862279D0 (no)	1986-06-06
EP0206021A1 (de)	1986-12-30
ZA864262B (en)	1987-02-25
PT82726A (de)	1986-07-01
DK268386D0 (da)	1986-06-06
EP0206021B1 (de)	1988-08-10
ES8705357A1 (es)	1987-05-01
PT82726B (pt)	1988-12-15
FI862431A (fi)	1986-12-09

Publication	Publication Date	Title
EP1024800B1 (en)	2002-08-21	Thyroxine analogues having no significant hormonal activity to treat malignant tumors
EP0028833B1 (en)	1984-01-25	Imidazole derivatives, their production and use
US5137918A (en)	1992-08-11	N-(2'-aminophenyl)-benzamide derivatives process for the preparation thereof and pharmaceutical compositions containing them
NO175620B (pt)	1994-08-01
IE56343B1 (en)	1991-07-03	Anti-inflammatory products derived from methylene-diphosphonic acid,and process for their preparation
NO862279L (no)	1986-12-09	Nye derivater av 1,1,2,2-tetrametyl-1,2-bis-(2-fluor-4-hydroksy-fenyl)-etaner.
NZ236200A (en)	1994-12-22	3-oxime-indol-2-one derivatives and pharmaceutical compositions
PT85337B (pt)	1990-04-30	Processo para a preparacao de derivados cicloalquilicos 4-piridil-substituidos e de composicoes farmaceuticas que os contem
EP0167204B1 (en)	1989-09-27	Method for improving the absorption and effectiveness of a catecholamine compound
BR112013023316B1 (pt)	2021-12-14	Derivados de difenila substituídos, seu uso e seu processo de preparação, e medicamento
RU2160729C2 (ru)	2000-12-20	Производные бензолсульфонамида, их получение и терапевтическое применение
CS200483B2 (en)	1980-09-15	Process for preparing 6-methyl-8-/2-methylsulphinylethyl/ergoline
EP0107963B1 (en)	1987-04-01	Indole derivatives
US4707498A (en)	1987-11-17	Fluorinated diaminoalkyne derivatives
EP0058009A1 (en)	1982-08-18	Novel benzanilide derivatives and pharmaceutical compositions containing them
FI80440B (fi)	1990-02-28	Analogifoerfarande foer framstaellning av terapeutiskt anvaendbara afidkolanderivat.
KR890000795B1 (ko)	1989-04-07	플루오르화 디아미노-헵텐 및 -헵틴 유도체 및 이의 제조방법
NO874139L (no)	1988-04-05	Diamin-platina(ii)-kompleksforbindelser med en hydroksylert 2-fenyl-indolring.
Shapiro et al.	1958	N, N'-Polymethylene-bis-anilines and Related Compounds
KR890000621B1 (ko)	1989-03-22	불소화된 디아미노알켄 유도체의 제조방법
Cohen et al.	1963	Some Derivatives of 2, 2'-(Phenylimino) diethanol
US3646144A (en)	1972-02-29	Drug with hypertensive action on the base of 1-(3 4 - dimethoxy - 4-hydroxyphenyl)-2-monomethylaminoethanol
KR820000097B1 (ko)	1982-02-17	피리도[2,1-b] 퀴나졸린 유도체의 제조방법
NO153172B (no)	1985-10-21	Analogifremgangsmaate ved fremstilling av terapeutisk aktive decarboxylaseinhiberende fluorerte alkandiaminderivater
KR810001887B1 (ko)	1981-11-20	페닐에틸아민류의 제조방법