CS208112B2 - Method of making the new fluoralcylsubstituted derivatives of theacylanilides - Google Patents
Method of making the new fluoralcylsubstituted derivatives of theacylanilides Download PDFInfo
- Publication number
- CS208112B2 CS208112B2 CS788289A CS828978A CS208112B2 CS 208112 B2 CS208112 B2 CS 208112B2 CS 788289 A CS788289 A CS 788289A CS 828978 A CS828978 A CS 828978A CS 208112 B2 CS208112 B2 CS 208112B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- carbon atoms
- trifluoromethyl
- nitro
- acylanilide
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- -1 chloro, bromo, iodo Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 239000000460 chlorine Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 230000002280 anti-androgenic effect Effects 0.000 abstract description 7
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000000203 mixture Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 150000003931 anilides Chemical class 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 5
- HPUAIGRGCRIKGO-UHFFFAOYSA-N 2-hydroxy-2-(trifluoromethyl)butanoic acid Chemical compound CCC(O)(C(O)=O)C(F)(F)F HPUAIGRGCRIKGO-UHFFFAOYSA-N 0.000 description 4
- FSBVERYRVPGNGG-UHFFFAOYSA-N dimagnesium dioxido-bis[[oxido(oxo)silyl]oxy]silane hydrate Chemical compound O.[Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O FSBVERYRVPGNGG-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 239000000391 magnesium silicate Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 229910000386 magnesium trisilicate Inorganic materials 0.000 description 3
- 235000019793 magnesium trisilicate Nutrition 0.000 description 3
- 229940099273 magnesium trisilicate Drugs 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- CTGJACFEVDCYMC-UHFFFAOYSA-N 3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid Chemical compound OC(=O)C(O)(C)C(F)(F)F CTGJACFEVDCYMC-UHFFFAOYSA-N 0.000 description 2
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 2
- HVPKIOUHNVOKDK-UHFFFAOYSA-N 3-methylnonan-3-yl acetate Chemical compound CCCCCCC(C)(CC)OC(C)=O HVPKIOUHNVOKDK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-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
- 239000003098 androgen Substances 0.000 description 2
- 239000000051 antiandrogen Substances 0.000 description 2
- 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- QBVHMPFSDVNFAY-UHFFFAOYSA-N 1,1,1-trifluorobutan-2-one Chemical compound CCC(=O)C(F)(F)F QBVHMPFSDVNFAY-UHFFFAOYSA-N 0.000 description 1
- HGANPMZHRFOEDM-UHFFFAOYSA-N 1,1,1-trifluorohexan-2-one Chemical compound CCCCC(=O)C(F)(F)F HGANPMZHRFOEDM-UHFFFAOYSA-N 0.000 description 1
- ZWXJKMUOASQXRN-UHFFFAOYSA-N 2-hydroxy-2-(trifluoromethyl)hexanoic acid Chemical compound CCCCC(O)(C(O)=O)C(F)(F)F ZWXJKMUOASQXRN-UHFFFAOYSA-N 0.000 description 1
- IZJXNNYTXBGURB-UHFFFAOYSA-N 3,3,3-trifluoro-2-methoxy-2-methylpropanoyl chloride Chemical group COC(C)(C(Cl)=O)C(F)(F)F IZJXNNYTXBGURB-UHFFFAOYSA-N 0.000 description 1
- LCJCHPHCCUYKRL-UHFFFAOYSA-N 3,3,3-trifluoro-2-methyl-2-phenylmethoxypropanoyl chloride Chemical compound ClC(=O)C(C(F)(F)F)(C)OCC1=CC=CC=C1 LCJCHPHCCUYKRL-UHFFFAOYSA-N 0.000 description 1
- FZLSDZZNPXXBBB-KDURUIRLSA-N 5-chloro-N-[3-cyclopropyl-5-[[(3R,5S)-3,5-dimethylpiperazin-1-yl]methyl]phenyl]-4-(6-methyl-1H-indol-3-yl)pyrimidin-2-amine Chemical compound C[C@H]1CN(Cc2cc(Nc3ncc(Cl)c(n3)-c3c[nH]c4cc(C)ccc34)cc(c2)C2CC2)C[C@@H](C)N1 FZLSDZZNPXXBBB-KDURUIRLSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- 241000965476 Darksidea beta Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 102000006771 Gonadotropins Human genes 0.000 description 1
- 108010086677 Gonadotropins Proteins 0.000 description 1
- 206010020112 Hirsutism Diseases 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- NOJWJVVRDOATPU-UHFFFAOYSA-M N[Cr](O)(=O)=O Chemical compound N[Cr](O)(=O)=O NOJWJVVRDOATPU-UHFFFAOYSA-M 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 241000209049 Poa pratensis Species 0.000 description 1
- PDMMFKSKQVNJMI-BLQWBTBKSA-N Testosterone propionate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CC)[C@@]1(C)CC2 PDMMFKSKQVNJMI-BLQWBTBKSA-N 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940046836 anti-estrogen Drugs 0.000 description 1
- 230000001833 anti-estrogenic effect Effects 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229960004397 cyclophosphamide Drugs 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 231100000599 cytotoxic agent Toxicity 0.000 description 1
- POZRVZJJTULAOH-LHZXLZLDSA-N danazol Chemical compound C1[C@]2(C)[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=CC2=C1C=NO2 POZRVZJJTULAOH-LHZXLZLDSA-N 0.000 description 1
- 229960000766 danazol Drugs 0.000 description 1
- IPIVAXLHTVNRBS-UHFFFAOYSA-N decanoyl chloride Chemical compound CCCCCCCCCC(Cl)=O IPIVAXLHTVNRBS-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000328 estrogen antagonist Substances 0.000 description 1
- 229960001347 fluocinolone acetonide Drugs 0.000 description 1
- FEBLZLNTKCEFIT-VSXGLTOVSA-N fluocinolone acetonide Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O FEBLZLNTKCEFIT-VSXGLTOVSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 1
- 229960002074 flutamide Drugs 0.000 description 1
- 239000002622 gonadotropin Substances 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- YPQLFJODEKMJEF-UHFFFAOYSA-N hydroxyflutamide Chemical compound CC(C)(O)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 YPQLFJODEKMJEF-UHFFFAOYSA-N 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 229960002985 medroxyprogesterone acetate Drugs 0.000 description 1
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000016087 ovulation Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 208000017497 prostate disease Diseases 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- 229960001712 testosterone propionate Drugs 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/01—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups
- C07C59/115—Saturated compounds having only one carboxyl group and containing hydroxy or O-metal groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/305—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups
- C07C59/315—Saturated compounds containing more than one carboxyl group containing ether groups, groups, groups, or groups containing halogen
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03B—APPARATUS OR ARRANGEMENTS FOR TAKING PHOTOGRAPHS OR FOR PROJECTING OR VIEWING THEM; APPARATUS OR ARRANGEMENTS EMPLOYING ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ACCESSORIES THEREFOR
- G03B31/00—Associated working of cameras or projectors with sound-recording or sound-reproducing means
- G03B31/02—Associated working of cameras or projectors with sound-recording or sound-reproducing means in which sound track is on a moving-picture film
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5222377 | 1977-12-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS208112B2 true CS208112B2 (en) | 1981-08-31 |
Family
ID=10463104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS788289A CS208112B2 (en) | 1977-12-15 | 1978-12-13 | Method of making the new fluoralcylsubstituted derivatives of theacylanilides |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4191775A (OSRAM) |
| EP (1) | EP0002892B1 (OSRAM) |
| JP (1) | JPS5495519A (OSRAM) |
| AT (1) | AT360974B (OSRAM) |
| AU (1) | AU522716B2 (OSRAM) |
| BG (1) | BG31225A3 (OSRAM) |
| CA (1) | CA1123008A (OSRAM) |
| CS (1) | CS208112B2 (OSRAM) |
| DD (1) | DD139844A5 (OSRAM) |
| DE (1) | DE2862459D1 (OSRAM) |
| DK (1) | DK556978A (OSRAM) |
| ES (1) | ES476049A1 (OSRAM) |
| FI (1) | FI70007C (OSRAM) |
| HU (1) | HU176981B (OSRAM) |
| IE (1) | IE49866B1 (OSRAM) |
| IL (1) | IL56155A (OSRAM) |
| IT (1) | IT1107675B (OSRAM) |
| NO (1) | NO149035C (OSRAM) |
| NZ (1) | NZ189086A (OSRAM) |
| PT (1) | PT68922A (OSRAM) |
| ZA (1) | ZA786781B (OSRAM) |
Families Citing this family (139)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ197008A (en) * | 1980-05-22 | 1984-10-19 | Ici Ltd | Acylanilide derivatives and pharmaceutical compositions |
| AU8961382A (en) * | 1981-11-06 | 1983-05-12 | Imperial Chemical Industries Plc | Amide derivatives |
| US5236953A (en) * | 1982-04-14 | 1993-08-17 | Imperial Chemical Industries Plc | Alkene, alkyne or cycloalkylene derivatives |
| GB8504093D0 (en) * | 1985-02-18 | 1985-03-20 | Ici Plc | Alkene alkyne/cycloalkylene derivatives |
| ATE28864T1 (de) * | 1982-07-23 | 1987-08-15 | Ici Plc | Amide-derivate. |
| US4885289A (en) * | 1983-12-12 | 1989-12-05 | Breuer Miklos M | Alteration of character of male beard growth |
| GB8406000D0 (en) * | 1984-03-07 | 1984-04-11 | Ici Plc | Olefine derivatives |
| GB8617652D0 (en) * | 1986-07-18 | 1986-08-28 | Ici Plc | Acylanilide derivatives |
| ATE79368T1 (de) * | 1987-05-22 | 1992-08-15 | Bracco Spa | Herstellung von 5-acylamino-2,4,6-trijodo- oder tribromo-benzoesaeure-derivate. |
| GB9214120D0 (en) * | 1991-07-25 | 1992-08-12 | Ici Plc | Therapeutic amides |
| WO1993008687A1 (en) * | 1991-11-05 | 1993-05-13 | Handelman Joseph H | Alteration of rate and character of hair growth |
| US5364885A (en) * | 1992-11-13 | 1994-11-15 | Ahluwalia Gurpreet S | Reduction of hair growth |
| US5411991A (en) * | 1992-12-22 | 1995-05-02 | Shander; Douglas | Method of reducing hair growth employing sulfhydryl active compounds |
| US6743419B1 (en) | 1992-12-22 | 2004-06-01 | The Gillette Company | Method of reducing hair growth employing sulfhydryl active compounds |
| GB9305295D0 (en) * | 1993-03-15 | 1993-05-05 | Zeneca Ltd | Therapeutic compounds |
| GB9310095D0 (en) * | 1993-05-17 | 1993-06-30 | Zeneca Ltd | Therapeutic compounds |
| US5648394A (en) * | 1993-05-27 | 1997-07-15 | Boxall; Brian Alfred | Topical composition for inhibiting hair growth |
| US6248751B1 (en) | 1993-05-28 | 2001-06-19 | Gurpreet S. Ahluwalia | Inhibition of hair growth |
| US6414017B2 (en) | 1993-05-28 | 2002-07-02 | The Gillette Company | Inhibition of hair growth |
| JPH0759644A (ja) * | 1993-08-24 | 1995-03-07 | Nobuyuki Yamamoto | 納骨用仏像 |
| US5474763A (en) * | 1994-03-11 | 1995-12-12 | Shander; Douglas | Reduction of hair growth |
| US5468476A (en) * | 1994-03-16 | 1995-11-21 | Ahluwalia; Gurpreet S. | Reduction of hair growth |
| US5455234A (en) * | 1994-03-16 | 1995-10-03 | Ahluwalia; Gurpreet S. | Inhibition of hair growth |
| ATE232743T1 (de) * | 1994-06-27 | 2003-03-15 | Neutron Therapies Inc | Bor enthaltende hormonanaloga und verfahren fuer ihre verwendung zur bildlichen darstellung oder zum abtoeten von zellen, die hormonrezeptoren besitzen |
| US5554608A (en) * | 1994-09-28 | 1996-09-10 | Ahluwalia; Gurpreet S. | Inhibition of hair growth |
| US5674477A (en) * | 1995-02-28 | 1997-10-07 | Ahluwalia; Gurpreet S. | Reduction of hair growth |
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| US5728736A (en) * | 1995-11-29 | 1998-03-17 | Shander; Douglas | Reduction of hair growth |
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| FR2747039B1 (fr) * | 1996-04-05 | 1998-05-22 | Oreal | Utilisation du n-(3,4-dicyano-phenyl)- 3,3,3-trifluoro- 2-hydroxy-2-methylpropionamide pour stimuler ou induire la pousse des cheveux et/ou stopper leur chute |
| FR2745717B1 (fr) * | 1996-03-06 | 1998-04-17 | Oreal | Utilisation de n-aryl-2-hydroxyalkylamides pour stimuler ou induire la pousse des cheveux et/ou stopper leur chute |
| WO1997032562A1 (fr) * | 1996-03-06 | 1997-09-12 | L'oreal | Utilisation de n-aryl-2-hydroxyalkylamides pour stimuler ou induire la pousse des cheveux et/ou stopper leur chute |
| US5908867A (en) * | 1996-07-18 | 1999-06-01 | Henry; James P. | Reduction of hair growth |
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| US7518013B2 (en) * | 2000-08-24 | 2009-04-14 | University Of Tennessee Research Foundation | Selective androgen receptor modulators |
| US6492554B2 (en) | 2000-08-24 | 2002-12-10 | The University Of Tennessee Research Corporation | Selective androgen receptor modulators and methods of use thereof |
| US6995284B2 (en) * | 2000-08-24 | 2006-02-07 | The University Of Tennessee Research Foundation | Synthesis of selective androgen receptor modulators |
| US7759520B2 (en) * | 1996-11-27 | 2010-07-20 | University Of Tennessee Research Foundation | Synthesis of selective androgen receptor modulators |
| US6071957A (en) * | 1996-11-27 | 2000-06-06 | The University Of Tennessee Research Corporation | Irreversible non-steroidal antagonist compound and its use in the treatment of prostate cancer |
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| WO1998053826A1 (en) * | 1997-05-30 | 1998-12-03 | The University Of Tennessee Research Corporation | Non-steroidal agonist compounds and their use in male hormone therapy |
| DE19723722A1 (de) * | 1997-05-30 | 1998-12-10 | Schering Ag | Nichtsteroidale Gestagene |
| US6019957A (en) * | 1997-06-04 | 2000-02-01 | The University Of Tennessee Research Corporation | Non-steroidal radiolabeled agonist/antagonist compounds and their use in prostate cancer imaging |
| US5939458A (en) * | 1997-09-22 | 1999-08-17 | Henry; James P. | Reduction of hair growth |
| US5958946A (en) * | 1998-01-20 | 1999-09-28 | Styczynski; Peter | Modulation of hair growth |
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| GB9804648D0 (en) | 1998-03-06 | 1998-04-29 | Zeneca Ltd | Chemical compounds |
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| GB9811427D0 (en) | 1998-05-29 | 1998-07-22 | Zeneca Ltd | Chemical compounds |
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| US6121269A (en) * | 1999-02-22 | 2000-09-19 | Henry; James P. | Reduction of hair growth |
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| US20040260108A1 (en) * | 2001-06-25 | 2004-12-23 | Dalton James T. | Metabolites of selective androgen receptor modulators and methods of use thereof |
| US7919647B2 (en) * | 2000-08-24 | 2011-04-05 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
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| US7645898B2 (en) * | 2000-08-24 | 2010-01-12 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and method of use thereof |
| US8445534B2 (en) * | 2000-08-24 | 2013-05-21 | University Of Tennessee Research Foundation | Treating androgen decline in aging male (ADAM)-associated conditions with SARMs |
| US7622503B2 (en) * | 2000-08-24 | 2009-11-24 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| US8008348B2 (en) * | 2001-12-06 | 2011-08-30 | University Of Tennessee Research Foundation | Treating muscle wasting with selective androgen receptor modulators |
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| DE10051981A1 (de) | 2000-10-20 | 2002-05-02 | Bayer Ag | Substituierte Phenyluracile |
| WO2002062341A1 (en) * | 2001-02-07 | 2002-08-15 | University Of Florida | Method and composition for the control of hair growth |
| US20040087548A1 (en) | 2001-02-27 | 2004-05-06 | Salvati Mark E. | Fused cyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
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| US20070161608A1 (en) * | 2001-12-06 | 2007-07-12 | Dalton James T | Selective androgen receptor modulators for treating muscle wasting |
| US8853266B2 (en) * | 2001-12-06 | 2014-10-07 | University Of Tennessee Research Foundation | Selective androgen receptor modulators for treating diabetes |
| KR100938188B1 (ko) | 2001-12-13 | 2010-01-21 | 스미또모 가가꾸 가부시키가이샤 | 비칼루타미드의 결정 및 그 제조 방법 |
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| DK1480634T3 (da) * | 2002-02-07 | 2011-11-14 | Univ Tennessee Res Foundation | Selektive androgenreceptormodulatorer (SARM) til behandling af benign prostatahyperplasi |
| US7803970B2 (en) * | 2002-02-28 | 2010-09-28 | University Of Tennessee Research Foundation | Multi-substitued selective androgen receptor modulators and methods of use thereof |
| US7772433B2 (en) * | 2002-02-28 | 2010-08-10 | University Of Tennessee Research Foundation | SARMS and method of use thereof |
| WO2003074450A2 (en) * | 2002-02-28 | 2003-09-12 | The University Of Tennessee Research Corporation | Radiolabeled selective androgen receptor modulators and their use in prostate cancer imaging and therapy |
| US7705182B2 (en) * | 2002-02-28 | 2010-04-27 | University Of Tennessee Research Foundation | Multi-substituted selective androgen receptor modulators and methods of use thereof |
| CN1639110A (zh) * | 2002-02-28 | 2005-07-13 | 田纳西大学研究基金会 | 卤代乙酰胺和叠氮化物取代的化合物及其使用方法 |
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| US7741371B2 (en) * | 2002-06-17 | 2010-06-22 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
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| JP2006505563A (ja) * | 2002-10-15 | 2006-02-16 | ジーティーエックス・インコーポレイテッド | 選択的アンドロゲン受容体調節剤による肥満治療 |
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| US9844528B2 (en) | 2006-08-24 | 2017-12-19 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
| HUE029808T2 (en) | 2006-08-24 | 2017-03-28 | Univ Tennessee Res Found | Substituted acylanilide derivatives and methods for their use |
| US9730908B2 (en) | 2006-08-24 | 2017-08-15 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
| US10010521B2 (en) | 2006-08-24 | 2018-07-03 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
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| US7968603B2 (en) | 2007-09-11 | 2011-06-28 | University Of Tennessee Research Foundation | Solid forms of selective androgen receptor modulators |
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| US10258596B2 (en) | 2012-07-13 | 2019-04-16 | Gtx, Inc. | Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS) |
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| US10987334B2 (en) | 2012-07-13 | 2021-04-27 | University Of Tennessee Research Foundation | Method of treating ER mutant expressing breast cancers with selective androgen receptor modulators (SARMs) |
| US9969683B2 (en) | 2012-07-13 | 2018-05-15 | Gtx, Inc. | Method of treating estrogen receptor (ER)-positive breast cancers with selective androgen receptor modulator (SARMS) |
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Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3995060A (en) * | 1972-06-20 | 1976-11-30 | Schering Corporation | Antiandrogenic agents and method for the treatment of androgen dependent disease states |
| DE1793110A1 (de) * | 1968-08-02 | 1971-12-16 | Basf Ag | Substituierte Saeureanilide |
| DE2042300A1 (de) * | 1970-08-26 | 1972-03-23 | Farbwerke Hoechst AG, vormals Meister Lucius & Brüning, 6000 Frankfurt | Halogencarbonsäureanilide, ihre Herstellung und Verwendung als Herbizide |
| CA1012462A (en) * | 1971-06-18 | 1977-06-21 | Scherico Ltd. | Pharmaceutical composition containing substituted anilides |
| US3875229A (en) * | 1972-11-24 | 1975-04-01 | Schering Corp | Substituted carboxanilides |
| JPS6044294B2 (ja) * | 1976-04-15 | 1985-10-02 | 帝国臓器製薬株式会社 | アニリド誘導体 |
-
1978
- 1978-11-29 US US05/964,726 patent/US4191775A/en not_active Expired - Lifetime
- 1978-11-30 IE IE2375/78A patent/IE49866B1/en unknown
- 1978-12-01 DE DE7878300716T patent/DE2862459D1/de not_active Expired
- 1978-12-01 EP EP78300716A patent/EP0002892B1/en not_active Expired
- 1978-12-01 CA CA317,202A patent/CA1123008A/en not_active Expired
- 1978-12-04 NZ NZ189086A patent/NZ189086A/xx unknown
- 1978-12-04 ZA ZA00786781A patent/ZA786781B/xx unknown
- 1978-12-05 AU AU42200/78A patent/AU522716B2/en not_active Expired
- 1978-12-07 IL IL56155A patent/IL56155A/xx unknown
- 1978-12-07 AT AT874278A patent/AT360974B/de active
- 1978-12-11 HU HU78IE853A patent/HU176981B/hu unknown
- 1978-12-11 DK DK556978A patent/DK556978A/da not_active Application Discontinuation
- 1978-12-13 IT IT52280/78A patent/IT1107675B/it active
- 1978-12-13 FI FI783820A patent/FI70007C/fi not_active IP Right Cessation
- 1978-12-13 CS CS788289A patent/CS208112B2/cs unknown
- 1978-12-14 NO NO784211A patent/NO149035C/no unknown
- 1978-12-15 BG BG041753A patent/BG31225A3/xx unknown
- 1978-12-15 ES ES476049A patent/ES476049A1/es not_active Expired
- 1978-12-15 JP JP15429978A patent/JPS5495519A/ja active Granted
- 1978-12-15 DD DD78209812A patent/DD139844A5/de unknown
- 1978-12-15 PT PT68922A patent/PT68922A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO784211L (no) | 1979-06-18 |
| NZ189086A (en) | 1980-09-12 |
| CA1123008A (en) | 1982-05-04 |
| IE49866B1 (en) | 1986-01-08 |
| NO149035C (no) | 1984-02-01 |
| ATA874278A (de) | 1980-07-15 |
| FI783820A7 (fi) | 1979-06-16 |
| EP0002892B1 (en) | 1985-02-06 |
| DE2862459D1 (en) | 1985-03-21 |
| AU4220078A (en) | 1979-06-21 |
| HU176981B (hu) | 1981-06-28 |
| AT360974B (de) | 1981-02-10 |
| FI70007B (fi) | 1986-01-31 |
| US4191775A (en) | 1980-03-04 |
| IT7852280A0 (it) | 1978-12-13 |
| BG31225A3 (bg) | 1981-11-16 |
| IL56155A0 (en) | 1979-03-12 |
| JPH0223537B2 (OSRAM) | 1990-05-24 |
| EP0002892A1 (en) | 1979-07-11 |
| ES476049A1 (es) | 1979-05-16 |
| DD139844A5 (de) | 1980-01-23 |
| IL56155A (en) | 1982-09-30 |
| FI70007C (fi) | 1986-09-12 |
| PT68922A (en) | 1979-01-01 |
| JPS5495519A (en) | 1979-07-28 |
| NO149035B (no) | 1983-10-24 |
| ZA786781B (en) | 1979-11-28 |
| IT1107675B (it) | 1985-11-25 |
| DK556978A (da) | 1979-06-16 |
| AU522716B2 (en) | 1982-06-24 |
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