NO811730L - Analogifremgangsmaate for fremstilling av fysiologisk aktive n-acylaniliner. - Google Patents
Analogifremgangsmaate for fremstilling av fysiologisk aktive n-acylaniliner.Info
- Publication number
- NO811730L NO811730L NO811730A NO811730A NO811730L NO 811730 L NO811730 L NO 811730L NO 811730 A NO811730 A NO 811730A NO 811730 A NO811730 A NO 811730A NO 811730 L NO811730 L NO 811730L
- Authority
- NO
- Norway
- Prior art keywords
- hydrogen
- hydroxy
- acylanilide
- nitro
- aniline
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
- 239000001257 hydrogen Substances 0.000 claims abstract description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
- 239000000460 chlorine Substances 0.000 claims abstract description 18
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- COWNFYYYZFRNOY-UHFFFAOYSA-N oxazolidinedione Chemical group O=C1COC(=O)N1 COWNFYYYZFRNOY-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052736 halogen Chemical group 0.000 claims abstract description 5
- 150000002367 halogens Chemical group 0.000 claims abstract description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000011737 fluorine Substances 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 37
- -1 cyano, carbamoyl Chemical group 0.000 claims description 37
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 28
- 239000007858 starting material Substances 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 150000002431 hydrogen Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 125000001589 carboacyl group Chemical group 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 6
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 150000002118 epoxides Chemical class 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 3
- JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical group [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 3
- KHINIKFJZOLDLA-UHFFFAOYSA-N 2-(4-cyanophenyl)-2-hydroxy-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=C(C#N)C=CC=1C(O)(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 KHINIKFJZOLDLA-UHFFFAOYSA-N 0.000 claims description 2
- TWOPCQYTPZCLNV-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-hydroxy-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=C(F)C=CC=1C(O)(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 TWOPCQYTPZCLNV-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- FXXVIZJCIASGGW-UHFFFAOYSA-N n-(3-chloro-4-nitrophenyl)-2-hydroxy-2-(4-nitrophenyl)propanamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(O)(C)C(=O)NC1=CC=C([N+]([O-])=O)C(Cl)=C1 FXXVIZJCIASGGW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 62
- 150000001875 compounds Chemical class 0.000 abstract description 20
- 230000002280 anti-androgenic effect Effects 0.000 abstract description 8
- CTXYKJLYJWMPQP-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-2-hydroxy-2-(4-nitrophenyl)propanamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(O)(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 CTXYKJLYJWMPQP-UHFFFAOYSA-N 0.000 abstract description 3
- 208000025844 Prostatic disease Diseases 0.000 abstract description 2
- 239000003098 androgen Substances 0.000 abstract description 2
- 230000001419 dependent effect Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 100
- 239000000243 solution Substances 0.000 description 70
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 44
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 229920006395 saturated elastomer Polymers 0.000 description 31
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 22
- 235000019341 magnesium sulphate Nutrition 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 239000011780 sodium chloride Substances 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000284 extract Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000012258 stirred mixture Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- UTKUVRNVYFTEHF-UHFFFAOYSA-N 4-nitro-3-(trifluoromethyl)aniline Chemical compound NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 UTKUVRNVYFTEHF-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- RBSRRICSXWXMRC-UHFFFAOYSA-N 2-(4-nitrophenyl)propanoic acid Chemical compound OC(=O)C(C)C1=CC=C([N+]([O-])=O)C=C1 RBSRRICSXWXMRC-UHFFFAOYSA-N 0.000 description 3
- AIXYAXPFWDFEOS-UHFFFAOYSA-N 2-acetyloxy-2-(4-nitrophenyl)propanoic acid Chemical compound CC(=O)OC(C)(C(O)=O)C1=CC=C([N+]([O-])=O)C=C1 AIXYAXPFWDFEOS-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- HAGFFASCRMUJPA-UHFFFAOYSA-N [N+](=O)([O-])C1=C2C(=C(C=C1)C(C(=O)OC)C)O2 Chemical compound [N+](=O)([O-])C1=C2C(=C(C=C1)C(C(=O)OC)C)O2 HAGFFASCRMUJPA-UHFFFAOYSA-N 0.000 description 3
- 150000003931 anilides Chemical class 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZZCVUIWOTANGSM-UHFFFAOYSA-N 2-(4-fluorophenyl)-2-hydroxypropanoic acid Chemical compound OC(=O)C(O)(C)C1=CC=C(F)C=C1 ZZCVUIWOTANGSM-UHFFFAOYSA-N 0.000 description 2
- BUYKQTWMLZLHDF-UHFFFAOYSA-N 2-hydroxy-2-(4-nitrophenyl)propanoic acid Chemical compound OC(=O)C(O)(C)C1=CC=C([N+]([O-])=O)C=C1 BUYKQTWMLZLHDF-UHFFFAOYSA-N 0.000 description 2
- SJUBAJPCMIJHEG-UHFFFAOYSA-N 2-methoxy-2-(4-nitrophenyl)propanoic acid Chemical compound COC(C)(C(O)=O)C1=CC=C([N+]([O-])=O)C=C1 SJUBAJPCMIJHEG-UHFFFAOYSA-N 0.000 description 2
- XCYAWTMSWQULHD-UHFFFAOYSA-N 4-amino-2-methylsulfanylbenzonitrile Chemical compound CSC1=CC(N)=CC=C1C#N XCYAWTMSWQULHD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 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
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 239000000051 antiandrogen Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 2
- 239000002024 ethyl acetate extract Substances 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- LWKCDROWKAJKMX-UHFFFAOYSA-N methyl 2-hydroxy-2-(4-nitrophenyl)propanoate Chemical compound COC(=O)C(C)(O)C1=CC=C([N+]([O-])=O)C=C1 LWKCDROWKAJKMX-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- AFENDNXGAFYKQO-VKHMYHEASA-N (S)-2-hydroxybutyric acid Chemical compound CC[C@H](O)C(O)=O AFENDNXGAFYKQO-VKHMYHEASA-N 0.000 description 1
- YEUYZNNBXLMFCW-UHFFFAOYSA-N 1-bromo-4-methylsulfanylbenzene Chemical compound CSC1=CC=C(Br)C=C1 YEUYZNNBXLMFCW-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- AOWYWBCBWDZRLG-UHFFFAOYSA-N 2-(4-acetylphenyl)-2-hydroxypropanoic acid Chemical compound CC(=O)C1=CC=C(C(C)(O)C(O)=O)C=C1 AOWYWBCBWDZRLG-UHFFFAOYSA-N 0.000 description 1
- JHQCUIXBZFIGCW-UHFFFAOYSA-N 2-(4-acetylphenyl)-n-(3,4-dichlorophenyl)-2-hydroxypropanamide Chemical compound C1=CC(C(=O)C)=CC=C1C(C)(O)C(=O)NC1=CC=C(Cl)C(Cl)=C1 JHQCUIXBZFIGCW-UHFFFAOYSA-N 0.000 description 1
- JJTPAASHRYIPIP-UHFFFAOYSA-N 2-(4-cyanophenyl)-2-hydroxypropanoic acid Chemical compound OC(=O)C(O)(C)C1=CC=C(C#N)C=C1 JJTPAASHRYIPIP-UHFFFAOYSA-N 0.000 description 1
- FUCJPEUCMWNZRF-UHFFFAOYSA-N 2-(4-nitrophenyl)-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 FUCJPEUCMWNZRF-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- YSIDNQSIVMLPCR-UHFFFAOYSA-N 2-butoxy-2-(4-nitrophenyl)-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(C)(OCCCC)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 YSIDNQSIVMLPCR-UHFFFAOYSA-N 0.000 description 1
- GWRFEDKLNIMMCQ-UHFFFAOYSA-N 2-butoxy-2-(4-nitrophenyl)propanoic acid Chemical compound CCCCOC(C)(C(O)=O)C1=CC=C([N+]([O-])=O)C=C1 GWRFEDKLNIMMCQ-UHFFFAOYSA-N 0.000 description 1
- LCYPKJKUNCZXAS-UHFFFAOYSA-N 2-hydroxy-2-(4-methylsulfinylphenyl)-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide Chemical compound C1=CC(S(=O)C)=CC=C1C(C)(O)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 LCYPKJKUNCZXAS-UHFFFAOYSA-N 0.000 description 1
- SWBSYLBIVWDCEV-UHFFFAOYSA-N 2-hydroxy-2-(4-methylsulfonylphenyl)-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C(O)(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 SWBSYLBIVWDCEV-UHFFFAOYSA-N 0.000 description 1
- ABNCIVVJUUQVGG-UHFFFAOYSA-N 2-hydroxy-2-(4-nitrophenyl)-n-(3,4,5-trichlorophenyl)propanamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(O)(C)C(=O)NC1=CC(Cl)=C(Cl)C(Cl)=C1 ABNCIVVJUUQVGG-UHFFFAOYSA-N 0.000 description 1
- ALQKIFUMTRMSEL-UHFFFAOYSA-N 2-hydroxy-2-(4-nitrophenyl)-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(O)(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 ALQKIFUMTRMSEL-UHFFFAOYSA-N 0.000 description 1
- WILAXPPGXUFLKL-UHFFFAOYSA-N 2-hydroxy-2-(4-nitrophenyl)propanenitrile Chemical compound N#CC(O)(C)C1=CC=C([N+]([O-])=O)C=C1 WILAXPPGXUFLKL-UHFFFAOYSA-N 0.000 description 1
- BRGSEHHSPCVJLH-UHFFFAOYSA-N 2-hydroxy-2-(4-phenylphenyl)propanoic acid Chemical compound C1=CC(C(O)(C(O)=O)C)=CC=C1C1=CC=CC=C1 BRGSEHHSPCVJLH-UHFFFAOYSA-N 0.000 description 1
- JRHWHSJDIILJAT-UHFFFAOYSA-N 2-hydroxypentanoic acid Chemical compound CCCC(O)C(O)=O JRHWHSJDIILJAT-UHFFFAOYSA-N 0.000 description 1
- VHIOKAHILDCQKV-UHFFFAOYSA-N 2-methoxy-2-(4-nitrophenyl)-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(C)(OC)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 VHIOKAHILDCQKV-UHFFFAOYSA-N 0.000 description 1
- AFRRWJPNQKSTEY-UHFFFAOYSA-N 2-methyl-2-(4-nitrophenyl)propanoic acid Chemical compound OC(=O)C(C)(C)C1=CC=C([N+]([O-])=O)C=C1 AFRRWJPNQKSTEY-UHFFFAOYSA-N 0.000 description 1
- NBBNQBRVECFIDX-UHFFFAOYSA-N 2-methylsulfanyl-4-nitrobenzamide Chemical compound CSC1=CC([N+]([O-])=O)=CC=C1C(N)=O NBBNQBRVECFIDX-UHFFFAOYSA-N 0.000 description 1
- HCFZFKHTTZBPNG-UHFFFAOYSA-N 2-methylsulfanyl-4-nitrobenzoic acid Chemical compound CSC1=CC([N+]([O-])=O)=CC=C1C(O)=O HCFZFKHTTZBPNG-UHFFFAOYSA-N 0.000 description 1
- WUEYEQNSYGIJMN-UHFFFAOYSA-N 2-methylsulfanyl-4-nitrobenzonitrile Chemical compound CSC1=CC([N+]([O-])=O)=CC=C1C#N WUEYEQNSYGIJMN-UHFFFAOYSA-N 0.000 description 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 description 1
- DEGWNSLUOMUQJM-UHFFFAOYSA-N 3-(5-chloro-6-hydroxy-6-nitrocyclohexa-2,4-dien-1-yl)-n-(3,4-dichlorophenyl)propanamide Chemical compound C1=CC=C(Cl)C(O)([N+]([O-])=O)C1CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 DEGWNSLUOMUQJM-UHFFFAOYSA-N 0.000 description 1
- UZHLBSQOUJCCCM-UHFFFAOYSA-N 3-chloro-2-hydroxy-2-(4-nitrophenyl)-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(CCl)(O)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 UZHLBSQOUJCCCM-UHFFFAOYSA-N 0.000 description 1
- PNDFVIHVLGBPOP-UHFFFAOYSA-N 3-chloro-n-(3-chloro-4-cyanophenyl)-2-hydroxy-2-(4-nitrophenyl)propanamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(CCl)(O)C(=O)NC1=CC=C(C#N)C(Cl)=C1 PNDFVIHVLGBPOP-UHFFFAOYSA-N 0.000 description 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- HQSCPPCMBMFJJN-UHFFFAOYSA-N 4-bromobenzonitrile Chemical compound BrC1=CC=C(C#N)C=C1 HQSCPPCMBMFJJN-UHFFFAOYSA-N 0.000 description 1
- YCZPVAWKLUWQBP-UHFFFAOYSA-N 4-isocyanato-1-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C=C1C(F)(F)F YCZPVAWKLUWQBP-UHFFFAOYSA-N 0.000 description 1
- YQYGPGKTNQNXMH-UHFFFAOYSA-N 4-nitroacetophenone Chemical compound CC(=O)C1=CC=C([N+]([O-])=O)C=C1 YQYGPGKTNQNXMH-UHFFFAOYSA-N 0.000 description 1
- QAYNSPOKTRVZRC-UHFFFAOYSA-N 99-60-5 Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1Cl QAYNSPOKTRVZRC-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
- 102000006771 Gonadotropins Human genes 0.000 description 1
- 108010086677 Gonadotropins Proteins 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 206010020112 Hirsutism Diseases 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000003810 Jones reagent Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 description 1
- 239000004100 Oxytetracycline Substances 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
- 206010039792 Seborrhoea Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- QEUYCNZDYQVMHS-UHFFFAOYSA-N [1-(3,4-dichloroanilino)-2-(4-nitrophenyl)-1-oxopropan-2-yl] acetate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(C)(OC(=O)C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 QEUYCNZDYQVMHS-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000004716 alpha keto acids Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- NWCHELUCVWSRRS-UHFFFAOYSA-N atrolactic acid Chemical compound OC(=O)C(O)(C)C1=CC=CC=C1 NWCHELUCVWSRRS-UHFFFAOYSA-N 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940117975 chromium trioxide Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 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
- 125000006612 decyloxy group Chemical group 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- MOUBYACUXWWHSC-UHFFFAOYSA-N diethyl 2-methyl-2-(4-nitrophenyl)propanedioate Chemical compound CCOC(=O)C(C)(C(=O)OCC)C1=CC=C([N+]([O-])=O)C=C1 MOUBYACUXWWHSC-UHFFFAOYSA-N 0.000 description 1
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 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
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 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
- 230000005484 gravity Effects 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000010438 heat treatment 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
- 239000005457 ice water Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- UWTCMGKGFSXLRK-UHFFFAOYSA-N methyl 2-(4-nitrophenyl)prop-2-enoate Chemical compound COC(=O)C(=C)C1=CC=C([N+]([O-])=O)C=C1 UWTCMGKGFSXLRK-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- SRJOXIQNBPPIFR-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-2-(4-formylphenyl)-2-hydroxypropanamide Chemical compound C=1C=C(C=O)C=CC=1C(O)(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 SRJOXIQNBPPIFR-UHFFFAOYSA-N 0.000 description 1
- OLPQMDTUZSJXCA-UHFFFAOYSA-N n-(3-chloro-4-methylsulfonylphenyl)-2-hydroxy-2-(4-nitrophenyl)propanamide Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(O)(C)C(=O)NC1=CC=C(S(C)(=O)=O)C(Cl)=C1 OLPQMDTUZSJXCA-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 230000016087 ovulation Effects 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229960000625 oxytetracycline Drugs 0.000 description 1
- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 description 1
- 235000019366 oxytetracycline Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000583 progesterone congener Substances 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 208000008742 seborrheic dermatitis Diseases 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000001625 seminal vesicle Anatomy 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229960001603 tamoxifen Drugs 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 201000010653 vesiculitis Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/44—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/56—Unsaturated compounds containing hydroxy or O-metal groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
- Steroid Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8016915 | 1980-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO811730L true NO811730L (no) | 1981-11-23 |
Family
ID=10513596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO811730A NO811730L (no) | 1980-05-22 | 1981-05-21 | Analogifremgangsmaate for fremstilling av fysiologisk aktive n-acylaniliner. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4386080A (pt) |
| EP (1) | EP0040932B1 (pt) |
| JP (1) | JPS5711951A (pt) |
| AT (1) | ATE14115T1 (pt) |
| AU (1) | AU543459B2 (pt) |
| CA (1) | CA1161850A (pt) |
| DE (1) | DE3171196D1 (pt) |
| DK (1) | DK219981A (pt) |
| ES (2) | ES502441A0 (pt) |
| FI (1) | FI811547L (pt) |
| GR (1) | GR75659B (pt) |
| HU (1) | HU185799B (pt) |
| IE (1) | IE51201B1 (pt) |
| IL (1) | IL62873A (pt) |
| NO (1) | NO811730L (pt) |
| NZ (1) | NZ197008A (pt) |
| PT (1) | PT73079B (pt) |
| YU (1) | YU130981A (pt) |
| ZA (1) | ZA813099B (pt) |
Families Citing this family (109)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4518789A (en) * | 1982-06-30 | 1985-05-21 | Yu Ruey J | Phenyl alpha-acyloxyacetamide derivatives and their therapeutic use |
| LU88769I2 (fr) * | 1982-07-23 | 1996-11-05 | Zeneca Ltd | Bicalutamide et ses sels et esters pharmaceutiquement acceptables (Casodex (R)) |
| US4536346A (en) * | 1983-05-06 | 1985-08-20 | American Cyanamid Company | Aralkanamidophenyl compounds |
| JPS60136546A (ja) * | 1983-12-26 | 1985-07-20 | Yashima Chem Ind Co Ltd | 置換フエニル酢酸アニリド誘導体、その製法及び用途 |
| GB8406000D0 (en) * | 1984-03-07 | 1984-04-11 | Ici Plc | Olefine derivatives |
| US4666885A (en) * | 1985-02-08 | 1987-05-19 | Fernand Labrie | Combination therapy for treatment of female breast cancer |
| US4760053A (en) * | 1984-08-02 | 1988-07-26 | Fernand Labrie | Combination therapy for selected sex steroid dependent cancers |
| GB8617653D0 (en) * | 1986-07-18 | 1986-08-28 | Ici Plc | Amide derivatives |
| GB8617652D0 (en) * | 1986-07-18 | 1986-08-28 | Ici Plc | Acylanilide derivatives |
| US4921941A (en) * | 1987-07-01 | 1990-05-01 | Schering Corporation | Orally active antiandrogens |
| US4895715A (en) * | 1988-04-14 | 1990-01-23 | Schering Corporation | Method of treating gynecomastia |
| US5204337A (en) * | 1988-10-31 | 1993-04-20 | Endorecherche Inc. | Estrogen nucleus derivatives for use in inhibition of sex steroid activity |
| US5372996A (en) * | 1989-03-10 | 1994-12-13 | Endorecherche, Inc. | Method of treatment of androgen-related diseases |
| US5364847A (en) * | 1989-03-10 | 1994-11-15 | Endorecherche | Inhibitors of sex steroid biosynthesis and methods for their production and use |
| JP2959839B2 (ja) * | 1989-07-07 | 1999-10-06 | アンドルシェルシュ・インコーポレイテッド | 性ステロイド活性の抑制における使用のためのアンドロゲン誘導体 |
| ATE230994T1 (de) * | 1989-07-07 | 2003-02-15 | Endorech Inc | Methode zur behandlung androgenbedingter krankheiten |
| US5260292A (en) * | 1991-03-05 | 1993-11-09 | Marvin S. Towsend | Topical treatment of acne with aminopenicillins |
| ZA924811B (en) * | 1991-06-28 | 1993-12-29 | Endorecherche Inc | Controlled release systems and low dose androgens |
| GB9214120D0 (en) * | 1991-07-25 | 1992-08-12 | Ici Plc | Therapeutic amides |
| SK140494A3 (en) * | 1992-05-21 | 1995-07-11 | Endorecherche Inc | Inhibitors of testosterone 5-alpha-reductase activity |
| GB9305295D0 (en) * | 1993-03-15 | 1993-05-05 | Zeneca Ltd | Therapeutic compounds |
| GB9310095D0 (en) * | 1993-05-17 | 1993-06-30 | Zeneca Ltd | Therapeutic compounds |
| EP0729363B1 (en) * | 1994-06-27 | 2003-02-19 | Neutron Therapies Inc. | Boron-containing hormone analogs and methods of their use in imaging or killing cells having hormone receptors |
| 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 |
| JP2000508296A (ja) | 1996-03-06 | 2000-07-04 | ロレアル | 髪の成長の刺激または誘発および／または抜毛防止のためのｎ―アリール―２―ヒドロキシアルキルアミドの使用 |
| US20050038110A1 (en) * | 2000-08-24 | 2005-02-17 | Steiner Mitchell S. | 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 |
| US6492554B2 (en) | 2000-08-24 | 2002-12-10 | The University Of Tennessee Research Corporation | Selective androgen receptor modulators and methods of use thereof |
| 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 |
| US7518013B2 (en) | 2000-08-24 | 2009-04-14 | University Of Tennessee Research Foundation | Selective androgen receptor modulators |
| US7759520B2 (en) | 1996-11-27 | 2010-07-20 | University Of Tennessee Research Foundation | Synthesis of selective androgen receptor modulators |
| DE19723722A1 (de) * | 1997-05-30 | 1998-12-10 | Schering Ag | Nichtsteroidale Gestagene |
| US6245804B1 (en) | 1997-05-30 | 2001-06-12 | Schering Aktiengesellschaft | Nonsteroidal gestagens |
| US6160011A (en) * | 1997-05-30 | 2000-12-12 | The University Of Tennessee Research Corporation | Non-steroidal agonist compounds and their use in male hormone therapy |
| AU7723198A (en) * | 1997-06-04 | 1998-12-21 | University Of Tennessee Research Corporation, The | Non-steroidal radiolabeled agonist/antagonist compounds and their use in prostate cancer imaging |
| GB9804648D0 (en) | 1998-03-06 | 1998-04-29 | Zeneca Ltd | Chemical compounds |
| GB9805520D0 (en) | 1998-03-17 | 1998-05-13 | Zeneca Ltd | Chemical compounds |
| US20040176470A1 (en) * | 1998-05-07 | 2004-09-09 | Steiner Mitchell S. | Method for treatment and chemoprevention of prostate cancer |
| GB9811427D0 (en) | 1998-05-29 | 1998-07-22 | Zeneca Ltd | Chemical compounds |
| ES2216940T3 (es) | 1999-09-04 | 2004-11-01 | Astrazeneca Ab | Derivados n-fenilicos de 2-hidroxi-2-metil-3,3,3-trifluoropropanamida sustituidos que elevan la actividad de piruvato deshidrogenasa. |
| WO2001017942A1 (en) | 1999-09-04 | 2001-03-15 | Astrazeneca Ab | Amides as inhibitors for pyruvate dehydrogenase |
| DE60031699T2 (de) | 1999-09-04 | 2007-08-30 | Astrazeneca Ab | Hydroxyacetamidobenzolsulfonamidderivate |
| US7645898B2 (en) | 2000-08-24 | 2010-01-12 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and method of use thereof |
| US8008348B2 (en) | 2001-12-06 | 2011-08-30 | University Of Tennessee Research Foundation | Treating muscle wasting with selective androgen receptor modulators |
| US7919647B2 (en) | 2000-08-24 | 2011-04-05 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| EP1705174A1 (en) | 2000-08-24 | 2006-09-27 | The University Of Tennessee Research Corporation | Selective androgen receptor modulators and methods 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 |
| US20070173546A1 (en) * | 2000-08-24 | 2007-07-26 | Dalton James T | Selective androgen receptor modulators and method of use thereof |
| US7026500B2 (en) | 2000-08-24 | 2006-04-11 | University Of Tennessee Research Foundation | Halogenated selective androgen receptor modulators and methods of use thereof |
| US7855229B2 (en) | 2000-08-24 | 2010-12-21 | University Of Tennessee Research Foundation | Treating wasting disorders with selective androgen receptor modulators |
| US20040260108A1 (en) * | 2001-06-25 | 2004-12-23 | Dalton James T. | Metabolites of selective androgen receptor modulators and methods of use thereof |
| US6998500B2 (en) | 2000-08-24 | 2006-02-14 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| US7622503B2 (en) | 2000-08-24 | 2009-11-24 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| US6838484B2 (en) | 2000-08-24 | 2005-01-04 | University Of Tennessee Research Foundation | Formulations comprising selective androgen receptor modulators |
| US20060287282A1 (en) * | 2001-06-25 | 2006-12-21 | Steiner Mitchell S | Compositions comprising a SARM ad GnRH agonist or a GnRH antagonist, and methods of use thereof |
| US7015253B2 (en) * | 2001-07-10 | 2006-03-21 | American Medical Systems, Inc. | Regimen for treating prostate tissue and surgical kit for use in the regimen |
| US8853266B2 (en) | 2001-12-06 | 2014-10-07 | University Of Tennessee Research Foundation | Selective androgen receptor modulators for treating diabetes |
| WO2003049675A2 (en) | 2001-12-06 | 2003-06-19 | Gtx, Inc. | Treating muscle wasting with selective androgen receptor modulators |
| US20070161608A1 (en) * | 2001-12-06 | 2007-07-12 | Dalton James T | Selective androgen receptor modulators for treating muscle wasting |
| BRPI0307699A2 (pt) | 2002-02-07 | 2015-06-16 | Gtx Inc | Tratamento de hiperplasia benigna da próstata com sarms. |
| KR20040101251A (ko) | 2002-02-28 | 2004-12-02 | 유니버시티 오브 테네시 리서치 파운데이션 | 다치환된 선택적 안드로겐 수용체 모듈레이터 및 이를사용하는 방법 |
| US7803970B2 (en) | 2002-02-28 | 2010-09-28 | University Of Tennessee Research Foundation | Multi-substitued selective androgen receptor modulators and methods of use thereof |
| AU2003217304A1 (en) | 2002-02-28 | 2003-09-16 | The University Of Tennessee Research Corporation | Radiolabeled selective androgen receptor modulators and their use in prostate cancer imaging and therapy |
| US7772433B2 (en) | 2002-02-28 | 2010-08-10 | University Of Tennessee Research Foundation | SARMS and method of use thereof |
| EP1487780A4 (en) * | 2002-02-28 | 2005-11-16 | Univ Tennessee Res Foundation | HALOGENACETAMIDE AND AZIDSUBSTITUTED COMPOUNDS AND METHOD FOR THEIR USE |
| US7741371B2 (en) | 2002-06-17 | 2010-06-22 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
| WO2003106401A1 (en) | 2002-06-17 | 2003-12-24 | University Of Tennessee Research Foundation | N-bridged selective androgen receptor modulators and methods of use thereof |
| EP1562594A4 (en) | 2002-10-15 | 2008-12-17 | Univ Tennessee Res Foundation | SELECTIVE ANDROGEN RECEPTOR MODULATORS WITH METHYLENE BRIDGES AND METHOD OF USE THEREOF |
| US20040197928A1 (en) * | 2002-10-15 | 2004-10-07 | Dalton James T. | Method for detecting selective androgen receptor modulators |
| AU2003287075A1 (en) * | 2002-10-15 | 2004-05-04 | Gtx, Inc. | Treating obesity with selective androgen receptor modulators |
| US20050080054A1 (en) * | 2002-10-16 | 2005-04-14 | Dalton James T. | Treating androgen decline in aging male (ADAM)-associated conditions with SARMS |
| US20060276539A1 (en) * | 2002-10-16 | 2006-12-07 | Dalton James T | Treating Androgen Decline in Aging Male (ADAM)- associated conditions with SARMS |
| US20040087810A1 (en) * | 2002-10-23 | 2004-05-06 | Dalton James T. | Irreversible selective androgen receptor modulators and methods of use thereof |
| US8309603B2 (en) | 2004-06-07 | 2012-11-13 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
| US20040167103A1 (en) * | 2003-02-24 | 2004-08-26 | Dalton James T. | Haloacetamide and azide substituted compounds and methods of use thereof |
| MXPA06000119A (es) | 2003-12-16 | 2006-03-21 | Gtx Inc | Profarmacos de moduladores receptores de androgenos selectivos y metodos de uso de los mismos. |
| WO2005110980A2 (en) | 2004-04-14 | 2005-11-24 | Amgen, Inc. | Aryl sulfones and uses related thereto |
| US20110237664A1 (en) * | 2004-06-07 | 2011-09-29 | Dalton James T | Selective androgen receptor modulators for treating diabetes |
| US9889110B2 (en) | 2004-06-07 | 2018-02-13 | University Of Tennessee Research Foundation | Selective androgen receptor modulator for treating hormone-related conditions |
| US9884038B2 (en) | 2004-06-07 | 2018-02-06 | University Of Tennessee Research Foundation | Selective androgen receptor modulator and methods of use thereof |
| US20060258628A1 (en) * | 2004-07-20 | 2006-11-16 | Steiner Mitchell S | Compositions comprising 5-alpha reductase inhibitors, and SARMs and methods of use thereof |
| US10010521B2 (en) | 2006-08-24 | 2018-07-03 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
| US9730908B2 (en) | 2006-08-24 | 2017-08-15 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
| JP5345534B2 (ja) | 2006-08-24 | 2013-11-20 | ユニバーシティ オブ テネシー リサーチ ファウンデーション | 置換アシルアニリドおよびそれらの使用方法 |
| US9844528B2 (en) | 2006-08-24 | 2017-12-19 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
| US9232959B2 (en) | 2007-01-02 | 2016-01-12 | Aquabeam, Llc | Multi fluid tissue resection methods and devices |
| JP5369336B2 (ja) | 2007-01-02 | 2013-12-18 | アクアビーム エルエルシー | 前立腺の疾患を治療するための侵襲性が最小である方法及びデバイス |
| US20080245375A1 (en) * | 2007-04-05 | 2008-10-09 | Medtronic Vascular, Inc. | Benign Prostatic Hyperplasia Treatments |
| US7968603B2 (en) | 2007-09-11 | 2011-06-28 | University Of Tennessee Research Foundation | Solid forms of selective androgen receptor modulators |
| JP5535925B2 (ja) | 2007-10-26 | 2014-07-02 | ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア | アンドロゲン受容体調節物質としてのジアリールヒダントイン化合物 |
| JP5506702B2 (ja) | 2008-03-06 | 2014-05-28 | アクアビーム エルエルシー | 流体流れ内を伝達される光学エネルギーによる組織切除および焼灼 |
| US9848904B2 (en) | 2009-03-06 | 2017-12-26 | Procept Biorobotics Corporation | Tissue resection and treatment with shedding pulses |
| EP2672958A1 (en) | 2011-02-08 | 2013-12-18 | Halozyme, Inc. | Composition and lipid formulation of a hyaluronan-degrading enzyme and the use thereof for treatment of benign prostatic hyperplasia |
| EP2729150B1 (en) * | 2011-07-08 | 2016-09-14 | Merck Sharp & Dohme Corp. | Factor ixa inhibitors |
| EP2819599B1 (en) | 2012-02-29 | 2018-05-23 | Procept Biorobotics Corporation | Automated image-guided tissue resection and treatment |
| US9622992B2 (en) | 2012-07-13 | 2017-04-18 | Gtx, Inc. | Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMs) |
| US9604916B2 (en) | 2012-07-13 | 2017-03-28 | Gtx, Inc. | Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (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) |
| US10258596B2 (en) | 2012-07-13 | 2019-04-16 | Gtx, Inc. | Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS) |
| US9744149B2 (en) | 2012-07-13 | 2017-08-29 | Gtx, Inc. | Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMs) |
| US10314807B2 (en) | 2012-07-13 | 2019-06-11 | Gtx, Inc. | Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS) |
| 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) |
| JP6403695B2 (ja) | 2013-02-14 | 2018-10-10 | プロセプト バイオロボティクス コーポレイション | アクアアブレーションアクアビーム眼科手術方法および装置 |
| CN109965976B (zh) | 2013-09-06 | 2022-05-31 | 普罗赛普特生物机器人公司 | 利用致脱脉冲的用于消融组织的装置 |
| BR112016031037B1 (pt) | 2014-06-30 | 2023-02-07 | Procept Biorobotics Corporation | Aparelho para ablação de tecido vascular |
| EP3188662A4 (en) | 2014-09-05 | 2018-05-23 | Procept Biorobotics Corporation | Physician controlled tissue resection integrated with treatment mapping of target organ images |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1878543A (en) * | 1929-12-23 | 1932-09-20 | Gen Aniline Works Inc | Monoaroyldiamines of the benzene series |
| US2721216A (en) * | 1953-02-18 | 1955-10-18 | Bristol Lab Inc | N-substituted mandelanilides |
| CH345016A (de) * | 1955-03-10 | 1960-03-15 | Farmaceutici Italia | Verfahren zur Herstellung von p-Oxy-phenylamiden |
| GB828695A (en) * | 1955-03-10 | 1960-02-24 | Farmaceutici Italia | N-p-hydroxylphenyl amides with choleretic action |
| US3214469A (en) * | 1958-01-15 | 1965-10-26 | Polaroid Corp | Dihydroxyphenylalkanoic acid amide derivatives |
| DE1160431B (de) * | 1962-03-06 | 1964-01-02 | Chem Fab Tempelhof Preuss & Te | Verfahren zur Herstellung des pharmakologisch wirksamen ª-Phenyl-ª, ª-diallylessigsaeure-p-hydroxyanilids |
| US3282939A (en) * | 1963-04-29 | 1966-11-01 | Geigy Chem Corp | Stabilization of organic material with stabilizers containing a substituted phenol group |
| DE1545803C3 (de) * | 1965-04-09 | 1974-01-31 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 7-Amino-Carbostyril-verbindungen |
| GB1113218A (en) * | 1965-11-01 | 1968-05-08 | Ucb Sa | New ether-amides |
| US3995060A (en) * | 1972-06-20 | 1976-11-30 | Schering Corporation | Antiandrogenic agents and method for the treatment of androgen dependent disease states |
| US3632829A (en) * | 1968-11-07 | 1972-01-04 | Monsanto Co | Halogenated mandelanilide carbanilates |
| US3706796A (en) * | 1970-11-25 | 1972-12-19 | Monsanto Co | Substituted amides |
| GB1405183A (en) * | 1972-12-18 | 1975-09-03 | Smidth & Co As F L | Support of rotary drums |
| US4049713A (en) * | 1974-07-23 | 1977-09-20 | Ciba-Geigy Corporation | Esters and amides of trisubstituted hydroxyphenylalkanoic acids |
| US4191775A (en) * | 1977-12-15 | 1980-03-04 | Imperial Chemical Industries Limited | Amide derivatives |
-
1981
- 1981-05-05 NZ NZ197008A patent/NZ197008A/en unknown
- 1981-05-07 IE IE1010/81A patent/IE51201B1/en unknown
- 1981-05-08 AU AU70295/81A patent/AU543459B2/en not_active Ceased
- 1981-05-08 GR GR64890A patent/GR75659B/el unknown
- 1981-05-08 ZA ZA00813099A patent/ZA813099B/xx unknown
- 1981-05-14 DE DE8181302147T patent/DE3171196D1/de not_active Expired
- 1981-05-14 EP EP81302147A patent/EP0040932B1/en not_active Expired
- 1981-05-14 AT AT81302147T patent/ATE14115T1/de not_active IP Right Cessation
- 1981-05-15 IL IL62873A patent/IL62873A/xx unknown
- 1981-05-19 DK DK219981A patent/DK219981A/da not_active Application Discontinuation
- 1981-05-19 FI FI811547A patent/FI811547L/fi not_active Application Discontinuation
- 1981-05-20 CA CA000377876A patent/CA1161850A/en not_active Expired
- 1981-05-20 HU HU811465A patent/HU185799B/hu unknown
- 1981-05-21 YU YU01309/81A patent/YU130981A/xx unknown
- 1981-05-21 US US06/266,047 patent/US4386080A/en not_active Expired - Fee Related
- 1981-05-21 NO NO811730A patent/NO811730L/no unknown
- 1981-05-22 ES ES502441A patent/ES502441A0/es active Granted
- 1981-05-22 JP JP7683281A patent/JPS5711951A/ja active Pending
- 1981-05-22 PT PT73079A patent/PT73079B/pt unknown
-
1982
- 1982-05-31 ES ES512702A patent/ES512702A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES8300088A1 (es) | 1982-10-01 |
| FI811547L (fi) | 1981-11-23 |
| PT73079A (en) | 1981-06-01 |
| EP0040932A1 (en) | 1981-12-02 |
| PT73079B (en) | 1982-07-15 |
| DE3171196D1 (en) | 1985-08-08 |
| YU130981A (en) | 1983-10-31 |
| IE51201B1 (en) | 1986-10-29 |
| EP0040932B1 (en) | 1985-07-03 |
| AU7029581A (en) | 1981-11-26 |
| GR75659B (pt) | 1984-08-02 |
| DK219981A (da) | 1981-11-23 |
| CA1161850A (en) | 1984-02-07 |
| ES8303285A1 (es) | 1983-02-01 |
| ES512702A0 (es) | 1983-02-01 |
| HU185799B (en) | 1985-03-28 |
| ZA813099B (en) | 1982-05-26 |
| IE811010L (en) | 1981-11-22 |
| IL62873A (en) | 1985-05-31 |
| NZ197008A (en) | 1984-10-19 |
| ATE14115T1 (de) | 1985-07-15 |
| JPS5711951A (en) | 1982-01-21 |
| ES502441A0 (es) | 1982-10-01 |
| US4386080A (en) | 1983-05-31 |
| AU543459B2 (en) | 1985-04-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO811730L (no) | Analogifremgangsmaate for fremstilling av fysiologisk aktive n-acylaniliner. | |
| EP0002892B1 (en) | Amide derivatives, process for their manufacture and pharmaceutical or veterinary compositions containing them | |
| US4282218A (en) | Amides | |
| US5604260A (en) | 5-methanesulfonamido-1-indanones as an inhibitor of cyclooxygenase-2 | |
| US4058558A (en) | Aromatic keto acids and derivatives having analgetic, antiinflammatory, and hypocholesterolemizing action | |
| US4008323A (en) | Method of reducing cholesterol using certain aromatic keto acids | |
| JPH0432061B2 (pt) | ||
| JPS6330458A (ja) | アシルアニリド，その製法及びこの化合物を含む黄体ホルモン様作用を有する医薬又は獣医薬組成物 | |
| JPS6036461A (ja) | 軟骨減成阻止剤およびその製法 | |
| US3707549A (en) | Alpha-substituted hydrocinnamic acids and derivatives thereof | |
| US3784602A (en) | Aryloxy-and arylthioalkanoic acids and esters and salts thereof | |
| US4118504A (en) | Isoindoline derivatives for treating pain | |
| JPH07215952A (ja) | カテコール誘導体 | |
| US3275685A (en) | [(1-alkenylsulfonyl)phenoxy] alkanoic acids | |
| US3450698A (en) | Phenthiazine derivatives | |
| AU637938B2 (en) | Phenoxyacetic acid compounds, method for production thereof, and pharmaceutical preparations containing same | |
| JPS5821626B2 (ja) | チカンサクサンユウドウタイ ノ セイゾウホウ | |
| JPS61268651A (ja) | フエニル酢酸誘導体およびその製造法 | |
| US6495713B2 (en) | Synthesis of ketosulfone esters | |
| SU873871A3 (ru) | Способ получени производных фенилуксусной кислоты | |
| JP4425373B2 (ja) | ヒドロキシ−２−ハロゲノピリジン誘導体の製造方法 | |
| KR820000625B1 (ko) | 아실아닐리드의 제조방법 | |
| JPS6253950A (ja) | ５，６−ジアルコキシアントラニル酸及びその製造法 | |
| JPS61221153A (ja) | ２−ヒドロキシ−３−ブテン酸エステル誘導体の製造方法 | |
| JPH03153660A (ja) | ４―ハロ―３―ヒドロキシブタンニトリルのスルホン酸エステルおよびその製造法 |