CA1249823A - Acylanilides having antiandrogenic properties - Google Patents
Acylanilides having antiandrogenic propertiesInfo
- Publication number
- CA1249823A CA1249823A CA000432811A CA432811A CA1249823A CA 1249823 A CA1249823 A CA 1249823A CA 000432811 A CA000432811 A CA 000432811A CA 432811 A CA432811 A CA 432811A CA 1249823 A CA1249823 A CA 1249823A
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- trifluoromethyl
- aniline
- acylanilide
- cyano
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 230000002280 anti-androgenic effect Effects 0.000 title abstract description 11
- -1 cyano, carbamoyl Chemical group 0.000 claims abstract description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 42
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 18
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000005864 Sulphur Substances 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 10
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Chemical group 0.000 claims abstract description 9
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 150000002367 halogens Chemical group 0.000 claims abstract description 7
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims abstract description 7
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 6
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000001301 oxygen Substances 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 86
- 239000000243 solution Substances 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 150000001875 compounds Chemical class 0.000 claims description 20
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 12
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000001589 carboacyl group Chemical group 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- COWNFYYYZFRNOY-UHFFFAOYSA-N oxazolidinedione Chemical group O=C1COC(=O)N1 COWNFYYYZFRNOY-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 150000003573 thiols Chemical class 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000002346 iodo group Chemical group I* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- QOYHJQHAECSGML-UHFFFAOYSA-N 2-hydroxy-2-methyl-3-[(4-methyl-1,3-thiazol-2-yl)sulfanyl]-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide Chemical compound CC1=CSC(SCC(C)(O)C(=O)NC=2C=C(C(=CC=2)[N+]([O-])=O)C(F)(F)F)=N1 QOYHJQHAECSGML-UHFFFAOYSA-N 0.000 claims description 2
- MPCNDLVBUWRIHK-UHFFFAOYSA-N 2-hydroxy-2-methyl-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide Chemical compound S1C(C)=NN=C1SCC(C)(O)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MPCNDLVBUWRIHK-UHFFFAOYSA-N 0.000 claims description 2
- QRNGZLXAQWWQRY-UHFFFAOYSA-N 2-hydroxy-2-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]-3-(1,3-thiazol-2-ylsulfanyl)propanamide Chemical compound C=1C=C([N+]([O-])=O)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CSC1=NC=CS1 QRNGZLXAQWWQRY-UHFFFAOYSA-N 0.000 claims description 2
- LTZBAGVQNRGURC-UHFFFAOYSA-N 2-hydroxy-2-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]-3-pyridin-2-ylsulfanylpropanamide Chemical compound C=1C=C([N+]([O-])=O)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CSC1=CC=CC=N1 LTZBAGVQNRGURC-UHFFFAOYSA-N 0.000 claims description 2
- YHVNIEINBWATCS-UHFFFAOYSA-N 2-hydroxy-2-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]-3-pyridin-2-ylsulfonylpropanamide Chemical compound C=1C=C([N+]([O-])=O)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=CC=N1 YHVNIEINBWATCS-UHFFFAOYSA-N 0.000 claims description 2
- ZMBWZDLDJNBWBB-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-2-hydroxy-2-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=C([N+]([O-])=O)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 ZMBWZDLDJNBWBB-UHFFFAOYSA-N 0.000 claims description 2
- HSGAFOSEUZZAIR-UHFFFAOYSA-N 3-(benzenesulfonyl)-2-hydroxy-2-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=C([N+]([O-])=O)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=CC=C1 HSGAFOSEUZZAIR-UHFFFAOYSA-N 0.000 claims description 2
- GDXNOJUTJPBYEC-UHFFFAOYSA-N 3-(benzenesulfonyl)-n-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=CC=C1 GDXNOJUTJPBYEC-UHFFFAOYSA-N 0.000 claims description 2
- OVADDGXJGBLCHW-UHFFFAOYSA-N 3-ethylsulfonyl-2-hydroxy-2-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide Chemical compound CCS(=O)(=O)CC(C)(O)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 OVADDGXJGBLCHW-UHFFFAOYSA-N 0.000 claims description 2
- LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 claims description 2
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 229940088710 antibiotic agent Drugs 0.000 claims description 2
- 239000003886 aromatase inhibitor Substances 0.000 claims description 2
- 229940046844 aromatase inhibitors Drugs 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 229940127089 cytotoxic agent Drugs 0.000 claims description 2
- 239000002254 cytotoxic agent Substances 0.000 claims description 2
- 231100000599 cytotoxic agent Toxicity 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 239000000262 estrogen Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 239000006210 lotion Substances 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- PVXXYTHVTHDYLF-UHFFFAOYSA-N n-(3-chloro-4-cyanophenyl)-3-ethylsulfanyl-2-hydroxy-2-methylpropanamide Chemical compound CCSCC(C)(O)C(=O)NC1=CC=C(C#N)C(Cl)=C1 PVXXYTHVTHDYLF-UHFFFAOYSA-N 0.000 claims description 2
- WLAFHQCIKGLYMU-UHFFFAOYSA-N n-(3-chloro-4-cyanophenyl)-3-ethylsulfonyl-2-hydroxy-2-methylpropanamide Chemical compound CCS(=O)(=O)CC(C)(O)C(=O)NC1=CC=C(C#N)C(Cl)=C1 WLAFHQCIKGLYMU-UHFFFAOYSA-N 0.000 claims description 2
- ZAIDIBQWPGBCIZ-UHFFFAOYSA-N n-(3-chloro-4-nitrophenyl)-2-hydroxy-2-methyl-3-phenylsulfanylpropanamide Chemical compound C=1C=C([N+]([O-])=O)C(Cl)=CC=1NC(=O)C(O)(C)CSC1=CC=CC=C1 ZAIDIBQWPGBCIZ-UHFFFAOYSA-N 0.000 claims description 2
- CDNBBHGMJBXAPS-UHFFFAOYSA-N n-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methyl-3-pyridin-2-ylsulfanylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CSC1=CC=CC=N1 CDNBBHGMJBXAPS-UHFFFAOYSA-N 0.000 claims description 2
- GCGWWKKSGPETMI-UHFFFAOYSA-N n-[4-cyano-3-(trifluoromethyl)phenyl]-3-(4-fluorophenyl)sulfanyl-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CSC1=CC=C(F)C=C1 GCGWWKKSGPETMI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 239000002674 ointment Substances 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
- 238000007911 parenteral administration Methods 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000000583 progesterone congener Substances 0.000 claims description 2
- 230000028327 secretion Effects 0.000 claims description 2
- 239000008174 sterile solution Substances 0.000 claims description 2
- 239000000829 suppository Substances 0.000 claims description 2
- 238000011200 topical administration Methods 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- NNGHXINSFWJBBD-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfanyl-2-hydroxy-2-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]propanamide Chemical compound C=1C=C([N+]([O-])=O)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CSC1=CC=C(F)C=C1 NNGHXINSFWJBBD-UHFFFAOYSA-N 0.000 claims 1
- 239000003972 antineoplastic antibiotic Substances 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims 1
- NMTGNGQASCLQGN-UHFFFAOYSA-N n-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methyl-3-(1,3-thiazol-2-ylsulfanyl)propanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CSC1=NC=CS1 NMTGNGQASCLQGN-UHFFFAOYSA-N 0.000 claims 1
- JYGCIZZUNXNFAT-UHFFFAOYSA-N n-[4-cyano-3-(trifluoromethyl)phenyl]-2-hydroxy-2-methylbutanethioamide Chemical compound CCC(C)(O)C(=S)NC1=CC=C(C#N)C(C(F)(F)F)=C1 JYGCIZZUNXNFAT-UHFFFAOYSA-N 0.000 claims 1
- PWGWGXQADJOTNC-UHFFFAOYSA-N n-[4-cyano-3-(trifluoromethyl)phenyl]-3-ethylsulfonyl-2-hydroxy-2-methylpropanamide Chemical compound CCS(=O)(=O)CC(C)(O)C(=O)NC1=CC=C(C#N)C(C(F)(F)F)=C1 PWGWGXQADJOTNC-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 abstract description 5
- 150000001408 amides Chemical class 0.000 abstract description 3
- 125000005277 alkyl imino group Chemical group 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
- 239000003208 petroleum Substances 0.000 description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000007858 starting material Substances 0.000 description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 239000000284 extract Substances 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000051 antiandrogen Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 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 3
- 229960002074 flutamide Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- YSLIVAGWSDUTLC-UHFFFAOYSA-N 2-hydroxy-2-methyl-3-phenylpropanethioic s-acid Chemical compound SC(=O)C(O)(C)CC1=CC=CC=C1 YSLIVAGWSDUTLC-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VCBRBUKGTWLJOB-UHFFFAOYSA-N Chloranocryl Chemical compound CC(=C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 VCBRBUKGTWLJOB-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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 150000007513 acids Chemical class 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
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- 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
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/84—Sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole 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
- C07D277/36—Sulfur atoms
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- 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
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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GB8221421 | 1982-07-23 | ||
GB8221421 | 1982-07-23 |
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CA1249823A true CA1249823A (en) | 1989-02-07 |
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CA000432811A Expired CA1249823A (en) | 1982-07-23 | 1983-07-20 | Acylanilides having antiandrogenic properties |
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US (1) | US4636505A (en, 2012) |
EP (1) | EP0100172B1 (en, 2012) |
JP (2) | JPS5933250A (en, 2012) |
AT (1) | ATE28864T1 (en, 2012) |
AU (1) | AU556328B2 (en, 2012) |
CA (1) | CA1249823A (en, 2012) |
CS (1) | CS399991A3 (en, 2012) |
DE (1) | DE3372965D1 (en, 2012) |
DK (1) | DK322783D0 (en, 2012) |
ES (4) | ES8601106A1 (en, 2012) |
FI (1) | FI83770C (en, 2012) |
GR (1) | GR79232B (en, 2012) |
HK (1) | HK92690A (en, 2012) |
HU (1) | HU191296B (en, 2012) |
IE (1) | IE55941B1 (en, 2012) |
IL (1) | IL69217A (en, 2012) |
LU (1) | LU88769I2 (en, 2012) |
MX (1) | MX9203451A (en, 2012) |
NL (1) | NL950029I2 (en, 2012) |
NO (2) | NO164974C (en, 2012) |
NZ (1) | NZ204995A (en, 2012) |
PT (1) | PT77087B (en, 2012) |
ZA (1) | ZA835182B (en, 2012) |
Families Citing this family (309)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS54115075A (en) * | 1978-02-28 | 1979-09-07 | Cho Lsi Gijutsu Kenkyu Kumiai | Plasma etching method |
FR2540495B1 (fr) * | 1983-02-07 | 1986-02-14 | Roussel Uclaf | Nouveaux derives de o-mercaptopropanamide et de ses homologues, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus |
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 |
US4970303A (en) * | 1988-02-03 | 1990-11-13 | Xoma Corporation | Linking agents and methods |
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 |
US5364847A (en) * | 1989-03-10 | 1994-11-15 | Endorecherche | Inhibitors of sex steroid biosynthesis and methods for their production and use |
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 |
GB9305295D0 (en) * | 1993-03-15 | 1993-05-05 | Zeneca Ltd | Therapeutic compounds |
GB9310095D0 (en) * | 1993-05-17 | 1993-06-30 | Zeneca Ltd | Therapeutic compounds |
EP0748220A4 (en) * | 1994-01-21 | 1997-09-10 | Sepracor Inc | METHOD AND COMPOSITIONS FOR TREATING ANDROGEN-DEPENDENT DISEASES USING OPTICALLY PURE R - (-) CASODEX |
DE4420777A1 (de) | 1994-06-15 | 1995-12-21 | Bayer Ag | Verfahren zur Herstellung von 4-Fluorthiophenol |
AU696788B2 (en) * | 1994-06-27 | 1998-09-17 | Neutron Therapies Inc. | Boron-containing hormone analogs and methods of their use in imaging or killing cells having hormone receptors |
US7205437B2 (en) * | 1996-11-27 | 2007-04-17 | 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 |
US7518013B2 (en) | 2000-08-24 | 2009-04-14 | University Of Tennessee Research Foundation | 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 |
US7759520B2 (en) | 1996-11-27 | 2010-07-20 | University Of Tennessee Research Foundation | Synthesis of selective androgen receptor modulators |
US20090264534A1 (en) * | 1996-11-27 | 2009-10-22 | Dalton James T | Selective androgen receptor modulators |
US20050038110A1 (en) * | 2000-08-24 | 2005-02-17 | Steiner Mitchell S. | Selective androgen receptor modulators and methods of use thereof |
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 |
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 |
DE19746512A1 (de) | 1997-10-22 | 1999-04-29 | Bayer Ag | Verfahren zur Herstellung von Arylmercaptanen durch Hydrierung von Diaryldisulfiden |
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 |
JP2003525856A (ja) * | 1998-08-28 | 2003-09-02 | スミスクライン・ビーチャム・コーポレイション | 2−アミノ−5−シアノフェノールの製法 |
US6184249B1 (en) | 1998-12-18 | 2001-02-06 | Biophysica, Inc. | Androgen receptor suppressors in the therapy and diagnosis of prostate cancer, alopecia and other hyper-androgenic syndromes |
US6472415B1 (en) * | 1998-12-18 | 2002-10-29 | Biophysica, Inc. | Androgen receptor suppressors in the therapy and diagnosis of prostate cancer, alopecia and other hyper-androgenic syndromes |
HU223950B1 (hu) * | 1999-06-10 | 2005-03-29 | Richter Gedeon Vegyészeti Gyár Rt. | Eljárás a racém, valamint az R-(-)- és S-(+)-N-[4-ciano-3-(trifluor-metil)-fenil]-3-[(4-fluor-fenil)-szulfonil]-2-hidroxi-2-metil-propánsavamid előállítására |
US6566372B1 (en) * | 1999-08-27 | 2003-05-20 | Ligand Pharmaceuticals Incorporated | Bicyclic androgen and progesterone receptor modulator compounds and methods |
HUP0202725A3 (en) | 1999-09-04 | 2005-04-28 | Astrazeneca Ab | Substituted n-phenyl 2-hydroxy-2-methyl-3,3,3-trifluoropropanamide derivatives which elevate pyruvate dehydrogenase activity, process for their preparation and pharmaceutical compositions containing them |
EP1214295B1 (en) | 1999-09-04 | 2006-11-02 | AstraZeneca AB | Hydroxyacetamidobenzenesulphonamide derivatives |
DE60039359D1 (de) | 1999-09-04 | 2008-08-14 | Astrazeneca Ab | Amide als pyruvatdehydrogenaseinhibitoren |
US6713454B1 (en) * | 1999-09-13 | 2004-03-30 | Nobex Corporation | Prodrugs of etoposide and etoposide analogs |
PL354620A1 (en) | 1999-10-19 | 2004-02-09 | Nobex Corporation | Methods of asymmetrically synthesizing enantiomers of casodex, its derivatives and intermediates thereof |
IL149256A0 (en) * | 1999-10-27 | 2002-11-10 | Nobex Corp | Resolution of intermediates in the synthesis of substantially pure bicalutamide |
GB9930839D0 (en) * | 1999-12-30 | 2000-02-16 | Pharmacia & Upjohn Spa | Process for treating gynecomastia |
GB0012291D0 (en) * | 2000-05-23 | 2000-07-12 | Astrazeneca Ab | Pharmaceutical combination |
GB0012293D0 (en) * | 2000-05-23 | 2000-07-12 | Astrazeneca Ab | Pharmaceutical combination |
MY128450A (en) | 2000-05-24 | 2007-02-28 | Upjohn Co | 1-(pyrrolidin-1-ylmethyl)-3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives |
US6828458B2 (en) | 2000-05-25 | 2004-12-07 | Biophysica, Inc. | Topical antiandrogen for hair loss and other hyperandrogenic conditions |
GB0016426D0 (en) * | 2000-07-05 | 2000-08-23 | Astrazeneca Ab | Pharmaceutical combination |
US7622503B2 (en) | 2000-08-24 | 2009-11-24 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
US20070173546A1 (en) * | 2000-08-24 | 2007-07-26 | Dalton James T | Selective androgen receptor modulators and method of use thereof |
JP2004518617A (ja) * | 2000-08-24 | 2004-06-24 | ザ・ユニバーシティ・オブ・テネシー・リサーチ・コーポレーション | 選択的アンドロゲン受容体モジュレーター及びその使用方法 |
US7026500B2 (en) * | 2000-08-24 | 2006-04-11 | University Of Tennessee Research Foundation | Halogenated selective androgen receptor modulators and methods of use thereof |
US7645898B2 (en) | 2000-08-24 | 2010-01-12 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and method of use thereof |
US20030232792A1 (en) * | 2000-08-24 | 2003-12-18 | Dalton James T. | 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 |
US7855229B2 (en) | 2000-08-24 | 2010-12-21 | University Of Tennessee Research Foundation | Treating wasting disorders 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 |
US8008348B2 (en) | 2001-12-06 | 2011-08-30 | University Of Tennessee Research Foundation | Treating muscle wasting with selective androgen receptor modulators |
US6998500B2 (en) | 2000-08-24 | 2006-02-14 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
US20040260108A1 (en) * | 2001-06-25 | 2004-12-23 | Dalton James T. | Metabolites of 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 |
US6562994B2 (en) * | 2000-09-21 | 2003-05-13 | Bristol-Myers Squibb Co. | Process for the preparation of N-(substituted phenyl)-3-alkyl-,aryl- and heteroarylsulfonyl-2-hydroxy-2-alkyl- and haloalkylpropanamide compounds |
EP2269603B1 (en) | 2001-02-19 | 2015-05-20 | Novartis AG | Treatment of breast tumors with a rapamycin derivative in combination with exemestane |
RU2003128971A (ru) * | 2001-02-27 | 2005-03-10 | Астразенека Аб (Se) | Фармацевтический препарат |
US6479692B1 (en) | 2001-05-02 | 2002-11-12 | Nobex Corporation | Methods of synthesizing acylanilides including bicalutamide and derivatives thereof |
DK1392313T3 (da) | 2001-05-16 | 2007-06-25 | Novartis Ag | Kombination omfattende N-{5-[4-(4-methyl-piperazino-methyl)-benzoyl-amido]-2-methylphenyl}-4-(3-pyridyl)-2-pyrimidin-amin og et biphosphonat |
EP1406855A4 (en) | 2001-06-13 | 2006-04-19 | Teva Gyogyszergyar Reszvenytar | NOVEL PROCESS FOR THE PREPARATION OF RAC-BICALUTAMIDE AND INTERMEDIATE PRODUCTS THEREOF |
US7102026B2 (en) * | 2001-06-13 | 2006-09-05 | Teva Gyógyszergyár Zártkörüen Müködö Részvénytársaság | Process for preparing and isolating rac-bicalutamide and its intermediates |
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 |
AU2002322493A1 (en) * | 2001-07-10 | 2003-01-29 | Ams Research Corporation | Surgical kit for treating prostate tissue |
US20060004042A1 (en) * | 2001-08-23 | 2006-01-05 | Dalton James T | Formulations comprising selective androgen receptor modulators |
SE0103424D0 (sv) * | 2001-10-15 | 2001-10-15 | Astrazeneca Ab | Pharmaceutical formulation |
AT410545B (de) * | 2001-11-07 | 2003-05-26 | Dsm Fine Chem Austria Gmbh | Verfahren zur herstellung von chiralen alpha-hydroxycarbonsäuren |
GB0128510D0 (en) * | 2001-11-28 | 2002-01-23 | Novartis Ag | Organic compounds |
DK1463497T3 (da) * | 2001-12-06 | 2012-01-30 | Gtx Inc | Behandling af muskelsvind med selektive androgenreceptormodulatorer |
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 |
EP1462442B1 (en) * | 2001-12-13 | 2009-08-26 | Sumitomo Chemical Company, Limited | Crystals of bicalutamide and process for their production |
CA2689080C (en) * | 2002-02-07 | 2011-07-05 | University Of Tennessee Research Foundation | Treating benign prostate hyperplasia with sarms |
JP4625637B2 (ja) | 2002-02-22 | 2011-02-02 | シャイア エルエルシー | 活性物質送達系及び活性物質を保護し投与する方法 |
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 |
US7344700B2 (en) | 2002-02-28 | 2008-03-18 | University Of Tennessee Research Corporation | Radiolabeled selective androgen receptor modulators and their use in prostate cancer imaging and therapy |
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 |
ATE533494T1 (de) * | 2002-02-28 | 2011-12-15 | Univ Tennessee Res Foundation | Mehrfach substituierte selektive androgen- rezeptor-modulatoren und anwendungsverfahren dafür |
GB0206215D0 (en) | 2002-03-15 | 2002-05-01 | Novartis Ag | Organic compounds |
MXPA04011384A (es) | 2002-05-16 | 2005-02-14 | Novartis Ag | Uso de agentes de union del receptor edg en cancer. |
US7741371B2 (en) | 2002-06-17 | 2010-06-22 | University Of Tennessee Research Foundation | Selective androgen receptor modulators and methods of use thereof |
JP2005529952A (ja) | 2002-06-17 | 2005-10-06 | 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 | N架橋選択的アンドロゲン受容体修飾物質及びその使用方法 |
AU2003248052A1 (en) | 2002-07-12 | 2004-02-02 | Yamanouchi Pharmaceutical Co., Ltd. | N-phenyl-(2r,5s)dimethylpiperadine derivative |
US20040063782A1 (en) * | 2002-09-27 | 2004-04-01 | Westheim Raymond J.H. | Bicalutamide forms |
US6818766B2 (en) * | 2002-10-02 | 2004-11-16 | Synthon Bv | Process for making bicalutamide and intermediates thereof |
EP1562906A4 (en) * | 2002-10-15 | 2009-12-02 | Univ Tennessee Res Foundation | HETEROCYCLIC SELECTIVE ANDROGEN RECEPTOR MODULATORS AND METHOD FOR THEIR USE |
CA2501797A1 (en) * | 2002-10-15 | 2004-04-29 | Gtx, Inc. | Treating obesity with selective androgen receptor modulators |
US20040197928A1 (en) * | 2002-10-15 | 2004-10-07 | Dalton James T. | Method for detecting selective androgen receptor modulators |
JP2006506369A (ja) * | 2002-10-15 | 2006-02-23 | 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 | メチレン架橋選択的アンドロゲン受容体調節剤及びその使用方法 |
US20060276539A1 (en) * | 2002-10-16 | 2006-12-07 | Dalton James T | Treating Androgen Decline in Aging Male (ADAM)- associated conditions with SARMS |
JP2006505564A (ja) * | 2002-10-16 | 2006-02-16 | ジーティーエックス・インコーポレイテッド | Sarmによる高齢男性のアンドロゲン減少に関連する病気の治療 |
US20040087810A1 (en) * | 2002-10-23 | 2004-05-06 | Dalton James T. | Irreversible selective androgen receptor modulators and methods of use thereof |
PL201540B1 (pl) * | 2002-10-30 | 2009-04-30 | Inst Farmaceutyczny | Sposób wytwarzania wysokiej czystości N-(4-cyjano-3-trifluorometylofenylo)-3-(4-fluorofenylosulfonylo)-2-hydroksy-2-metylopropanamidu |
PL201541B1 (pl) * | 2002-10-30 | 2009-04-30 | Inst Farmaceutyczny | Sposób wytwarzania N-(4-cyjano-3-trifluorometylofenylo)-2,3-epoksy-2-metylopropanamidu |
US8309603B2 (en) | 2004-06-07 | 2012-11-13 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
DK1592658T3 (da) | 2003-01-13 | 2013-07-29 | Univ Tennessee Res Foundation | Syntese af selektive, androgene receptormodulatorer i stor målestok |
US7332525B2 (en) * | 2003-01-17 | 2008-02-19 | Castle Erik P | Method of treatment of prostate cancer and composition for treatment thereof |
US20050020675A1 (en) * | 2003-02-21 | 2005-01-27 | Parthasaradhi Reddy Bandi | Bicalutamide polymorphs |
US20040167103A1 (en) * | 2003-02-24 | 2004-08-26 | Dalton James T. | Haloacetamide and azide substituted compounds and methods of use thereof |
EP1596857B1 (en) | 2003-02-27 | 2008-10-29 | Wisconsin Alumni Research Foundation | Pmcol for the treatment of prostate cancer |
US20050008691A1 (en) * | 2003-05-14 | 2005-01-13 | Arturo Siles Ortega | Bicalutamide compositions |
AU2003247740A1 (en) * | 2003-06-25 | 2005-02-14 | Teva Gyogyszergyar Reszventarsasag | Process for purifying and isolating rac-bicalutamide |
CN100462353C (zh) * | 2003-06-27 | 2009-02-18 | 奥赖恩公司 | 用作雄激素受体调节剂的丙酰胺衍生物 |
DE602004026583D1 (de) * | 2003-06-27 | 2010-05-27 | Orion Corp | Als androgenrezeptormodulatoren geeignete propionamidderivate |
FI20030958A0 (fi) * | 2003-06-27 | 2003-06-27 | Orion Corp | Uusia yhdisteitä |
MXPA06000794A (es) | 2003-07-22 | 2006-08-23 | Astex Therapeutics Ltd | Compuestos 1h-pirazola 3,4-disustituida y su uso como moduladores de quinasas dependientes de ciclina (cdk) y quinasa-3 de sintasa de glicogeno (gsr-3). |
JP2005060302A (ja) * | 2003-08-12 | 2005-03-10 | Sumitomo Chemical Co Ltd | N−メタクリロイル−4−シアノ−3−トリフルオロメチルアニリンの製造方法および安定化方法 |
CN1838956A (zh) | 2003-08-22 | 2006-09-27 | 配体药物公司 | 作为雄激素受体调节剂化合物的6-环氨基-2-喹啉酮衍生物 |
AU2004281708B2 (en) * | 2003-10-14 | 2011-02-17 | University Of Tennessee Research Foundation | Treating bone-related disorders with selective androgen receptor modulators |
TW200523235A (en) * | 2003-10-15 | 2005-07-16 | Gtx Inc | Anti-cancer compounds and methods of use thereof |
RU2422450C2 (ru) | 2003-11-19 | 2011-06-27 | Метабазис Терапеутикс, Инк. | Новые фосфорсодержащие тиромиметики |
AU2004305061A1 (en) | 2003-12-16 | 2005-07-07 | Gtx, Inc. | Prodrugs of selective androgen receptor modulators and methods of use thereof |
US20050250709A1 (en) * | 2003-12-19 | 2005-11-10 | Bionaut Pharmaceuticals | Anti-neoplastic agents, combination therapies and related methods |
BRPI0507670A (pt) | 2004-02-13 | 2007-07-17 | Warner Lambert Co | moduladores do receptor de androgênio |
US8519158B2 (en) | 2004-03-12 | 2013-08-27 | Ligand Pharmaceuticals Incorporated | Androgen receptor modulator compounds and methods |
KR20080083220A (ko) | 2004-04-07 | 2008-09-16 | 노파르티스 아게 | Iap 억제제 |
BRPI0509759A (pt) | 2004-04-13 | 2007-10-16 | Warner Lambert Co | moduladores de androgênio |
EP1740533A1 (en) | 2004-04-22 | 2007-01-10 | Warner-Lambert Company LLC | Androgen modulators |
EA011306B8 (ru) * | 2004-06-07 | 2012-10-30 | Юниверсити Оф Теннесси Рисерч Фаундейшн | Избирательные модуляторы андрогеновых рецепторов и способы их применения |
US9884038B2 (en) | 2004-06-07 | 2018-02-06 | University Of Tennessee Research Foundation | Selective androgen receptor modulator and methods of use thereof |
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 |
ITMI20041222A1 (it) | 2004-06-17 | 2004-09-17 | Cosma S P A | Procedimento perfezionato per la sintesi di bicalutamide |
GB0512324D0 (en) | 2005-06-16 | 2005-07-27 | Novartis Ag | Organic compounds |
EP1781598A1 (en) | 2004-07-08 | 2007-05-09 | Warner-Lambert Company LLC | Androgen modulators |
NZ552392A (en) | 2004-07-14 | 2010-02-26 | Sumitomo Chemical Co | Method of crystallizing bicalutamide |
US20060258628A1 (en) * | 2004-07-20 | 2006-11-16 | Steiner Mitchell S | Compositions comprising 5-alpha reductase inhibitors, and SARMs and methods of use thereof |
US20060135468A1 (en) * | 2004-09-02 | 2006-06-22 | Bionaut Pharmaceuticals, Inc. | Treatment of refractory cancers using NA+/K+ ATPase inhibitors |
WO2006028969A1 (en) * | 2004-09-02 | 2006-03-16 | Bionaut Pharmaceuticals, Inc. | Pancreatic cancer treatment using na+/k+ atpase inhibitors |
US20070105790A1 (en) * | 2004-09-02 | 2007-05-10 | Bionaut Pharmaceuticals, Inc. | Pancreatic cancer treatment using Na+/K+ ATPase inhibitors |
US20060135441A1 (en) * | 2004-09-02 | 2006-06-22 | Bionaut Pharmaceuticals, Inc. | Combinatorial chemotherapy treatment using Na+/K+ ATPase inhibitors |
US20080027010A1 (en) * | 2004-09-02 | 2008-01-31 | Bionaut Pharmaceuticals, Inc. | Treatment of refractory cancers using Na+/K+-ATPase inhibitors |
EP1812010A2 (en) * | 2004-10-18 | 2007-08-01 | BTG International Limited | Use of na+/ k+-atpase inhibitors and antagonists thereof |
US20060159767A1 (en) * | 2004-12-22 | 2006-07-20 | Elan Pharma International Limited | Nanoparticulate bicalutamide formulations |
US8404718B2 (en) | 2005-01-21 | 2013-03-26 | Astex Therapeutics Limited | Combinations of pyrazole kinase inhibitors |
WO2006077428A1 (en) | 2005-01-21 | 2006-07-27 | Astex Therapeutics Limited | Pharmaceutical compounds |
AR054425A1 (es) | 2005-01-21 | 2007-06-27 | Astex Therapeutics Ltd | Sales de adicion de piperidin 4-il- amida de acido 4-(2,6-dicloro-benzoilamino) 1h-pirazol-3-carboxilico. |
RU2436575C2 (ru) * | 2005-01-21 | 2011-12-20 | Астекс Терапьютикс Лимитед | Соединения для использования в фармацевтике |
EP1863759A1 (en) * | 2005-03-29 | 2007-12-12 | Usv Limited | Process for preparation of bicalutamide |
TW200724139A (en) | 2005-05-05 | 2007-07-01 | Warner Lambert Co | Androgen modulators |
US7709517B2 (en) * | 2005-05-13 | 2010-05-04 | The Regents Of The University Of California | Diarylhydantoin compounds |
GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
US7709516B2 (en) | 2005-06-17 | 2010-05-04 | Endorecherche, Inc. | Helix 12 directed non-steroidal antiandrogens |
NZ560354A (en) * | 2005-06-17 | 2010-10-29 | Ligand Pharm Inc | Androgen receptor modulator compounds and methods |
CA2513356A1 (en) * | 2005-07-26 | 2007-01-26 | Apotex Pharmachem Inc. | Process for production of bicalutamide |
CA2623034A1 (en) | 2005-09-27 | 2007-04-05 | Novartis Ag | Carboxyamine compounds and their use in the treatment of hdac dependent diseases |
US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
PT2275103E (pt) | 2005-11-21 | 2014-07-24 | Novartis Ag | Inibidores de mtor para o tratamento de tumores endócrinos |
US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
AU2006329551A1 (en) * | 2005-12-27 | 2007-07-05 | Dabur Pharma Limited | An improved process for preparation of Bicalutamide |
JP5373405B2 (ja) * | 2006-03-03 | 2013-12-18 | オリオン コーポレーション | 選択的アンドロゲン受容体モジュレーター |
GB0605120D0 (en) | 2006-03-14 | 2006-04-26 | Novartis Ag | Organic Compounds |
MX2008012492A (es) | 2006-03-29 | 2008-12-12 | Univ California | Compuestos de diariltiohidantoina. |
EP2591775A1 (en) | 2006-04-05 | 2013-05-15 | Novartis AG | Combinations comprising mtor inhibitors for treating cancer |
EP2314297A1 (en) | 2006-04-05 | 2011-04-27 | Novartis AG | Combinations comprising bcr-abl/c-kit/pdgf-r tk inhibitors for treating cancer |
AR078793A1 (es) | 2006-04-07 | 2011-12-07 | Orion Corp | Derivados de carboxamidas no esteroidales y acil hidrazona moduladores de receptores androgenicos de tejido selectivo (sarm), composiciones farmaceuticas que los contienen y uso de los mismos en el tratamiento del cancer de prostata entre otros |
AU2007247112B2 (en) | 2006-05-09 | 2010-08-26 | Novartis Ag | Combination comprising an iron chelator and an anti-neoplastic agent and use thereof |
WO2008013791A2 (en) * | 2006-07-24 | 2008-01-31 | University Of Delaware | Pan-antagonists for the androgen receptor and androgen receptor mutants associated with anti-androgen withdrawal |
US9844528B2 (en) | 2006-08-24 | 2017-12-19 | 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 |
US10010521B2 (en) | 2006-08-24 | 2018-07-03 | University Of Tennessee Research Foundation | SARMs and method of use thereof |
PT2054049E (pt) | 2006-08-24 | 2016-06-02 | Univ Tennessee Res Found | Acilanilidas substituídas e métodos de utilização das mesmas |
CN101516885A (zh) | 2006-09-29 | 2009-08-26 | 诺瓦提斯公司 | 作为pi3k脂质激酶抑制剂的吡唑并嘧啶类化合物 |
WO2008044033A1 (en) * | 2006-10-11 | 2008-04-17 | Astrazeneca Ab | Amide derivatives |
EP2073803B1 (en) | 2006-10-12 | 2018-09-19 | Astex Therapeutics Limited | Pharmaceutical combinations |
EP2073807A1 (en) | 2006-10-12 | 2009-07-01 | Astex Therapeutics Limited | Pharmaceutical combinations |
WO2008070496A2 (en) | 2006-12-01 | 2008-06-12 | Bristol-Myers Squibb Company | N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
EP4566557A3 (en) | 2007-01-02 | 2025-08-27 | AquaBeam LLC | Minimally invasive devices for the treatment of prostate diseases |
US9232959B2 (en) | 2007-01-02 | 2016-01-12 | Aquabeam, Llc | Multi fluid tissue resection methods and devices |
US12290277B2 (en) | 2007-01-02 | 2025-05-06 | Aquabeam, Llc | Tissue resection with pressure sensing |
WO2008100985A2 (en) | 2007-02-15 | 2008-08-21 | Novartis Ag | Combination of lbh589 with other therapeutic agents for treating cancer |
US20080245375A1 (en) * | 2007-04-05 | 2008-10-09 | Medtronic Vascular, Inc. | Benign Prostatic Hyperplasia Treatments |
US9284345B2 (en) | 2007-04-12 | 2016-03-15 | Endorecherche, Inc. | 17alpha-substituted steroids as systemic antiandrogens and selective androgen receptor modulators |
US8110550B2 (en) | 2007-06-06 | 2012-02-07 | University Of Maryland, Baltimore | HDAC inhibitors and hormone targeted drugs for the treatment of cancer |
US7968603B2 (en) | 2007-09-11 | 2011-06-28 | University Of Tennessee Research Foundation | Solid forms of selective androgen receptor modulators |
US20090076158A1 (en) * | 2007-09-13 | 2009-03-19 | Protia, Llc | Deuterium-enriched bicalutamide |
EP2220050A2 (en) | 2007-10-26 | 2010-08-25 | The Regents Of The University Of California | Diarylhydantoin compounds as androgen receptor modulators |
ES2769535T3 (es) | 2008-03-06 | 2020-06-26 | Aquabeam Llc | Ablación de tejido y cauterización con energía óptica transportada en una corriente de fluido |
KR101673621B1 (ko) | 2008-03-24 | 2016-11-07 | 노파르티스 아게 | 아릴술폰아미드-계 매트릭스 메탈로프로테아제 억제제 |
MY150437A (en) | 2008-03-26 | 2014-01-30 | Novartis Ag | Hydroxamate-based inhibitors of deacetylases b |
WO2010083617A1 (en) | 2009-01-21 | 2010-07-29 | Oncalis Ag | Pyrazolopyrimidines as protein kinase inhibitors |
JP2012516345A (ja) | 2009-01-29 | 2012-07-19 | ノバルティス アーゲー | 星細胞腫治療用置換ベンゾイミダゾール |
US20120046364A1 (en) | 2009-02-10 | 2012-02-23 | Metabasis Therapeutics, Inc. | Novel Sulfonic Acid-Containing Thyromimetics, and Methods for Their Use |
US9848904B2 (en) | 2009-03-06 | 2017-12-26 | Procept Biorobotics Corporation | Tissue resection and treatment with shedding pulses |
WO2014127242A2 (en) | 2013-02-14 | 2014-08-21 | Procept Biorobotics Corporation | Aquablation aquabeam eye surgery methods and apparatus |
US8741951B2 (en) | 2009-04-10 | 2014-06-03 | CNR—Consiglio Nazionale Delle Ricerche | Non-steroidal compounds for androgen receptor modulation |
ITBO20090235A1 (it) * | 2009-04-10 | 2010-10-11 | Consiglio Nazionale Ricerche | Composti per il trattamento del tumore alla prostata e procedimenti per la loro sintesi |
KR101360725B1 (ko) | 2009-06-26 | 2014-02-07 | 노파르티스 아게 | Cyp17의 억제제로서의 1,3-이치환된 이미다졸리딘-2-온 유도체 |
US8450374B2 (en) * | 2009-06-29 | 2013-05-28 | University Of Delaware | Pan-antagonists for the androgen receptor and androgen receptor mutants associated with anti-androgen withdrawal |
US8389526B2 (en) | 2009-08-07 | 2013-03-05 | Novartis Ag | 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives |
US8497368B2 (en) | 2009-08-12 | 2013-07-30 | Novartis Ag | Heterocyclic hydrazone compounds |
KR20120089463A (ko) | 2009-08-20 | 2012-08-10 | 노파르티스 아게 | 헤테로시클릭 옥심 화합물 |
CN102574785A (zh) | 2009-08-26 | 2012-07-11 | 诺瓦提斯公司 | 四取代的杂芳基化合物和它们作为mdm2和/或mdm4调节剂的用途 |
WO2011029915A1 (en) | 2009-09-10 | 2011-03-17 | Novartis Ag | Ether derivatives of bicyclic heteroaryls |
EP2496575B1 (en) | 2009-11-04 | 2014-04-30 | Novartis AG | Heterocyclic sulfonamide derivatives useful as mek inhibitors |
US20120289501A1 (en) | 2009-11-25 | 2012-11-15 | Novartis Ag | Benzene-fused 6-membered oxygen-containing heterocyclic derivatives of bicyclic heteroaryls |
WO2011064663A1 (en) | 2009-11-25 | 2011-06-03 | Festuccia, Claudio | Combination treatment employing belinostat and bicalutamide |
AU2012265844A1 (en) | 2009-12-08 | 2013-05-02 | Novartis Ag | Heterocyclic sulfonamide derivatives |
BR112012013735A2 (pt) | 2009-12-08 | 2019-09-24 | Novartis Ag | derivados heterocícilicos de sulfonamida |
US8440693B2 (en) | 2009-12-22 | 2013-05-14 | Novartis Ag | Substituted isoquinolinones and quinazolinones |
CU24130B1 (es) | 2009-12-22 | 2015-09-29 | Novartis Ag | Isoquinolinonas y quinazolinonas sustituidas |
CN101759597B (zh) * | 2009-12-31 | 2013-09-04 | 上海康鹏化学有限公司 | 2-三氟甲基-4-氨基苯腈的制备方法 |
JP2013516501A (ja) * | 2010-01-11 | 2013-05-13 | ジーティーエックス・インコーポレイテッド | マイボーム腺機能障害を治療する方法 |
CN102947274A (zh) | 2010-06-17 | 2013-02-27 | 诺瓦提斯公司 | 联苯基取代的1,3-二氢-苯并咪唑-2-亚基胺衍生物 |
JP2013532149A (ja) | 2010-06-17 | 2013-08-15 | ノバルティス アーゲー | ピペリジニル置換1,3−ジヒドロ−ベンゾイミダゾール−2−イリデンアミン誘導体 |
UA112517C2 (uk) | 2010-07-06 | 2016-09-26 | Новартіс Аг | Тетрагідропіридопіримідинові похідні |
FI20105806A0 (fi) | 2010-07-15 | 2010-07-15 | Medeia Therapeutics Ltd | Uudet aryyliamidijohdannaiset, joilla on antiandrogeenisia ominaisuuksia |
US8946260B2 (en) | 2010-09-16 | 2015-02-03 | Novartis Ag | 17α-hydroxylase/C17,20-lyase inhibitors |
WO2012042532A1 (en) | 2010-09-29 | 2012-04-05 | Shilpa Medicare Limited | Process for preparing bicalutamide |
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 |
WO2012107500A1 (en) | 2011-02-10 | 2012-08-16 | Novartis Ag | [1, 2, 4] triazolo [4, 3 -b] pyridazine compounds as inhibitors of the c-met tyrosine kinase |
JP2014507465A (ja) | 2011-03-08 | 2014-03-27 | ノバルティス アーゲー | フルオロフェニル二環式ヘテロアリール化合物 |
EA024245B1 (ru) | 2011-04-21 | 2016-08-31 | Орион Корпорейшн | Карбоксамиды, модулирующие андрогенные рецепторы |
MX359399B (es) | 2011-04-28 | 2018-09-27 | Novartis Ag | Inhibidores de 17alfa-hidroxilasa/c17-20-liasa. |
WO2012158707A1 (en) | 2011-05-16 | 2012-11-22 | Genzyme Corporation | Use of cxcr4 antagonists |
US8859535B2 (en) | 2011-06-20 | 2014-10-14 | Novartis Ag | Hydroxy substituted isoquinolinone derivatives |
US8859586B2 (en) | 2011-06-20 | 2014-10-14 | Novartis Ag | Cyclohexyl isoquinolinone compounds |
MX2013015001A (es) | 2011-06-27 | 2014-03-31 | Novartis Ag | Formas solidas y sales de derivados de tetrahidro-pirido-pirimidin a. |
JP5957526B2 (ja) | 2011-09-15 | 2016-07-27 | ノバルティス アーゲー | チロシンキナーゼとしての6−置換3−(キノリン−6−イルチオ)−[1,2,4]トリアゾロ[4,3−a]ピラジン |
EP2785717B1 (en) | 2011-11-29 | 2016-01-13 | Novartis AG | Pyrazolopyrrolidine compounds |
HRP20191982T4 (hr) | 2011-11-30 | 2023-01-06 | Astrazeneca Ab | Kombinacijsko liječenje raka |
EP2794594A1 (en) | 2011-12-22 | 2014-10-29 | Novartis AG | Quinoline derivatives |
MA37142B1 (fr) | 2011-12-22 | 2019-07-31 | Novartis Ag | Dérivés de dihydro-benzo-oxazine et de dihydro-pyrido-oxazine |
US9126980B2 (en) | 2011-12-23 | 2015-09-08 | Novartis Ag | Compounds for inhibiting the interaction of BCL2 with binding partners |
JP2015503518A (ja) | 2011-12-23 | 2015-02-02 | ノバルティス アーゲー | Bcl2と結合相手の相互作用を阻害するための化合物 |
EP2794592A1 (en) | 2011-12-23 | 2014-10-29 | Novartis AG | Compounds for inhibiting the interaction of bcl2 with binding partners |
JP2015503516A (ja) | 2011-12-23 | 2015-02-02 | ノバルティス アーゲー | Bcl2と結合相手の相互作用を阻害するための化合物 |
US20140357666A1 (en) | 2011-12-23 | 2014-12-04 | Novartis Ag | Compounds for inhibiting the interaction of bcl2 with binding partners |
MX356499B (es) | 2012-01-13 | 2018-05-30 | Medeia Therapeutics Ltd | Derivados de heteroarilamida novedosos que tienen propiedades antiandrogénicas. |
AR089701A1 (es) | 2012-01-13 | 2014-09-10 | Medeia Therapeutics Ltd | Derivados de arilamida que tienen propiedades antiandrogenicas |
AR089703A1 (es) | 2012-01-13 | 2014-09-10 | Medeia Therapeutics Ltd | Derivados de arilamida que tienen propiedades antiandrogenicas |
UY34591A (es) | 2012-01-26 | 2013-09-02 | Novartis Ag | Compuestos de imidazopirrolidinona |
EP3351196A1 (en) | 2012-02-29 | 2018-07-25 | Procept Biorobotics Corporation | Automated image-guided tissue resection and treatment |
EP2834246B1 (en) | 2012-04-03 | 2021-07-28 | Novartis AG | Combination products with tyrosine kinase inhibitors and their use |
WO2013152170A1 (en) | 2012-04-04 | 2013-10-10 | Catylix, Inc. | Selective androgen receptor modulators |
AU2013204533B2 (en) | 2012-04-17 | 2017-02-02 | Astrazeneca Ab | Crystalline forms |
US20130310387A1 (en) | 2012-05-16 | 2013-11-21 | Novartis Ag | Monocyclic Heteroaryl Cycloalkyldiamine Derivatives |
CN104321325B (zh) | 2012-05-24 | 2016-11-16 | 诺华股份有限公司 | 吡咯并吡咯烷酮化合物 |
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) |
HRP20201463T1 (hr) | 2012-07-13 | 2021-04-02 | Oncternal Therapeutics, Inc. | Postupak liječenja raka dojke selektivnim modulatorom androgenskog receptora (sarm) |
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) |
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) |
US10258596B2 (en) | 2012-07-13 | 2019-04-16 | 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) |
US10314807B2 (en) | 2012-07-13 | 2019-06-11 | Gtx, Inc. | Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS) |
EP2882747B1 (en) | 2012-08-13 | 2016-04-27 | Novartis AG | Bicyclic heteroaryl cycloalkyldiamine derivatives as inhibitors of spleen tyrosine kinases (syk) |
WO2014053491A1 (en) | 2012-10-02 | 2014-04-10 | Epitherapeutics Aps | Inhibitors of histone demethylases |
TW201422625A (zh) | 2012-11-26 | 2014-06-16 | Novartis Ag | 二氫-吡啶并-□衍生物之固體形式 |
RU2510392C1 (ru) * | 2012-12-21 | 2014-03-27 | Федеральное государственное бюджетное учреждение науки Институт химии растворов им. Г.А. Крестова Российской академии наук (ИХР РАН) | Сокристаллическая форма бикалутамида |
EP2948451B1 (en) | 2013-01-22 | 2017-07-12 | Novartis AG | Substituted purinone compounds |
US9556180B2 (en) | 2013-01-22 | 2017-01-31 | Novartis Ag | Pyrazolo[3,4-d]pyrimidinone compounds as inhibitors of the P53/MDM2 interaction |
WO2014128612A1 (en) | 2013-02-20 | 2014-08-28 | Novartis Ag | Quinazolin-4-one derivatives |
JP6514117B2 (ja) | 2013-02-27 | 2019-05-15 | エピセラピューティクス アーペーエス | ヒストン脱メチル化酵素の阻害剤 |
WO2014155268A2 (en) | 2013-03-25 | 2014-10-02 | Novartis Ag | Fgf-r tyrosine kinase activity inhibitors - use in diseases associated with lack of or reduced snf5 activity |
US20150018376A1 (en) | 2013-05-17 | 2015-01-15 | Novartis Ag | Pyrimidin-4-yl)oxy)-1h-indole-1-carboxamide derivatives and use thereof |
UY35675A (es) | 2013-07-24 | 2015-02-27 | Novartis Ag | Derivados sustituidos de quinazolin-4-ona |
WO2015022663A1 (en) | 2013-08-14 | 2015-02-19 | Novartis Ag | Compounds and compositions as inhibitors of mek |
WO2015022664A1 (en) | 2013-08-14 | 2015-02-19 | Novartis Ag | Compounds and compositions as inhibitors of mek |
US9227969B2 (en) | 2013-08-14 | 2016-01-05 | Novartis Ag | Compounds and compositions as inhibitors of MEK |
JP6461971B2 (ja) | 2013-09-06 | 2019-01-30 | プロセプト バイオロボティクス コーポレイション | 飛散パルスを用いた組織切除および処置 |
AU2014321420B2 (en) | 2013-09-22 | 2017-06-15 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine compounds and methods of use |
TW201605450A (zh) | 2013-12-03 | 2016-02-16 | 諾華公司 | Mdm2抑制劑與BRAF抑制劑之組合及其用途 |
US9682960B2 (en) | 2013-12-19 | 2017-06-20 | Endorecherche, Inc. | Non-steroidal antiandrogens and selective androgen receptor modulators with a pyridyl moiety |
CN103772238B (zh) * | 2014-01-24 | 2017-03-22 | 苏州伊莱特新药研发有限公司 | 一类新的含酯基芳香丙酰胺化合物及其制备方法和用途 |
US9394281B2 (en) | 2014-03-28 | 2016-07-19 | Calitor Sciences, Llc | Substituted heteroaryl compounds and methods of use |
JP2017512804A (ja) | 2014-03-31 | 2017-05-25 | ギリアード サイエンシーズ, インコーポレイテッド | ヒストン脱メチル化酵素の阻害剤 |
WO2015196144A2 (en) | 2014-06-20 | 2015-12-23 | England Pamela M | Androgen receptor antagonists |
CN106572864B (zh) | 2014-06-30 | 2020-06-09 | 普罗赛普特生物机器人公司 | 流体射流组织切除和寒凝装置 |
CN104151197B (zh) * | 2014-07-25 | 2017-02-22 | 苏州伊莱特新药研发有限公司 | 芳香丙酰胺类化合物及其制备方法和应用 |
WO2016011658A1 (en) | 2014-07-25 | 2016-01-28 | Novartis Ag | Combination therapy |
WO2016016822A1 (en) | 2014-07-31 | 2016-02-04 | Novartis Ag | Combination therapy |
AR101692A1 (es) | 2014-08-27 | 2017-01-04 | Epitherapeutics Aps | Compuestos y métodos para inhibir histonas demetilasas |
EP4477143A3 (en) | 2014-09-05 | 2025-03-19 | PROCEPT BioRobotics Corporation | Physician controlled tissue resection integrated with treatment mapping of target organ images |
WO2016079522A1 (en) | 2014-11-20 | 2016-05-26 | University College Cardiff Consultants Limited | Androgen receptor modulators and their use as anti-cancer agents |
WO2016079521A1 (en) | 2014-11-20 | 2016-05-26 | University College Cardiff Consultants Limited | Androgen receptor modulators and their use as anti-cancer agents |
US10017471B2 (en) | 2015-04-21 | 2018-07-10 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
US10806720B2 (en) | 2015-04-21 | 2020-10-20 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
US10441570B2 (en) | 2015-04-21 | 2019-10-15 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) Ligands and methods of use thereof |
US9834507B2 (en) | 2015-04-21 | 2017-12-05 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
US10035763B2 (en) | 2015-04-21 | 2018-07-31 | Gtx, Inc. | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
US10865184B2 (en) | 2015-04-21 | 2020-12-15 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
US10654809B2 (en) | 2016-06-10 | 2020-05-19 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
CA2983426C (en) | 2015-04-21 | 2023-10-17 | Gtx, Inc. | Selective androgen receptor degrader (sard) ligands and methods of use thereof |
US10093613B2 (en) | 2015-04-21 | 2018-10-09 | Gtx, Inc. | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
MX2017013563A (es) | 2015-04-21 | 2018-07-06 | Gtx Inc | LIGANDOS DEGRADADORES SELECTIVOS DEL RECEPTOR ANDROGíNICO (SARD) Y SUS MíTODOS DE USO. |
WO2017044434A1 (en) | 2015-09-11 | 2017-03-16 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use |
US11230523B2 (en) | 2016-06-10 | 2022-01-25 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (SARD) ligands and methods of use thereof |
CN106748884B (zh) * | 2016-12-13 | 2021-08-20 | 山西振东制药股份有限公司 | 一种比卡鲁胺中间体的制备方法 |
WO2019099311A1 (en) | 2017-11-19 | 2019-05-23 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use |
US11602534B2 (en) | 2017-12-21 | 2023-03-14 | Hefei Institutes Of Physical Science, Chinese Academy Of Sciences | Pyrimidine derivative kinase inhibitors |
KR102737185B1 (ko) | 2018-01-20 | 2024-12-05 | 선샤인 레이크 파르마 컴퍼니 리미티드 | 치환된 아미노피리미딘 화합물 및 이의 사용 방법 |
WO2020051344A1 (en) | 2018-09-05 | 2020-03-12 | University Of Tennessee Research Foundation | Selective androgen receptor degrader (sard) ligands and methods of use thereof |
JP2022509917A (ja) | 2018-11-05 | 2022-01-25 | ファイザー・インク | がんを処置するための組合せ |
CN109438297B (zh) * | 2018-12-03 | 2021-05-14 | 昆明积大制药股份有限公司 | 雄激素受体拮抗剂、其制备方法及其应用 |
KR20220003554A (ko) | 2019-04-19 | 2022-01-10 | 리간드 파마슈티칼스 인코포레이티드 | 화합물의 결정질 형태 및 결정질 형태를 제조하는 방법 |
MX2021013774A (es) | 2019-05-14 | 2021-12-10 | Nuvation Bio Inc | Compuestos anticancerigenos dirigidos a los receptores hormonales nucleares. |
MX2023001823A (es) | 2020-08-13 | 2023-03-13 | Pfizer | Terapia de combinacion. |
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WO2025045058A1 (zh) * | 2023-08-28 | 2025-03-06 | 中国药科大学 | 作为雄激素受体拮抗剂的化合物 |
WO2025067483A1 (zh) * | 2023-09-28 | 2025-04-03 | 中国药科大学 | 酰胺类化合物 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3133119A (en) * | 1961-11-09 | 1964-05-12 | Givaudan Corp | Substituted acetanilides and propionanilides |
US3995060A (en) * | 1972-06-20 | 1976-11-30 | Schering Corporation | Antiandrogenic agents and method for the treatment of androgen dependent disease states |
CH493198A (de) * | 1968-05-06 | 1970-07-15 | Ciba Geigy | Schädlingsbekämpfungsmittel |
FR2142803A1 (en) * | 1971-06-25 | 1973-02-02 | Scherico Ltd | 3,4-disubstd anilides - having antiandrogenic activity |
US3875229A (en) * | 1972-11-24 | 1975-04-01 | Schering Corp | Substituted carboxanilides |
US4144270A (en) * | 1973-04-19 | 1979-03-13 | Schering Corporation | Substituted anilides as anti-androgens |
US4329364A (en) * | 1974-09-11 | 1982-05-11 | Schering Corporation | Antiandrogenic agents and methods for the treatment of androgen dependent disease states |
US4039684A (en) * | 1976-03-25 | 1977-08-02 | Schering Corporation | Method for treatment of canine seborrhea |
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 |
US4139638A (en) * | 1976-09-23 | 1979-02-13 | Schering Corporation | Methods for the treatment of hirsutism |
EP0002309B1 (en) * | 1977-10-12 | 1982-12-01 | Imperial Chemical Industries Plc | Acylanilides, process for their manufacture and pharmaceutical and veterinary compositions containing them |
US4191775A (en) * | 1977-12-15 | 1980-03-04 | Imperial Chemical Industries Limited | Amide derivatives |
NZ197008A (en) * | 1980-05-22 | 1984-10-19 | Ici Ltd | Acylanilide derivatives and pharmaceutical compositions |
-
1983
- 1983-07-08 EP EP83303998A patent/EP0100172B1/en not_active Expired
- 1983-07-08 LU LU88769C patent/LU88769I2/fr unknown
- 1983-07-08 DE DE8383303998T patent/DE3372965D1/de not_active Expired
- 1983-07-08 AT AT83303998T patent/ATE28864T1/de active
- 1983-07-12 GR GR71917A patent/GR79232B/el unknown
- 1983-07-13 IL IL69217A patent/IL69217A/xx not_active IP Right Cessation
- 1983-07-13 DK DK3227/83A patent/DK322783D0/da not_active Application Discontinuation
- 1983-07-15 ZA ZA835182A patent/ZA835182B/xx unknown
- 1983-07-15 US US06/514,332 patent/US4636505A/en not_active Expired - Lifetime
- 1983-07-18 AU AU16937/83A patent/AU556328B2/en not_active Expired
- 1983-07-18 NO NO832599A patent/NO164974C/no not_active IP Right Cessation
- 1983-07-18 HU HU832531A patent/HU191296B/hu unknown
- 1983-07-20 JP JP58131085A patent/JPS5933250A/ja active Granted
- 1983-07-20 FI FI832644A patent/FI83770C/fi not_active IP Right Cessation
- 1983-07-20 CA CA000432811A patent/CA1249823A/en not_active Expired
- 1983-07-22 IE IE1732/83A patent/IE55941B1/en not_active IP Right Cessation
- 1983-07-22 NZ NZ204995A patent/NZ204995A/en unknown
- 1983-07-22 PT PT77087A patent/PT77087B/pt unknown
- 1983-07-22 ES ES524392A patent/ES8601106A1/es not_active Expired
-
1985
- 1985-01-16 ES ES539615A patent/ES8607915A1/es not_active Expired
- 1985-01-16 ES ES539614A patent/ES8607936A1/es not_active Expired
- 1985-06-14 ES ES544189A patent/ES8700231A1/es not_active Expired
-
1989
- 1989-09-07 JP JP1230574A patent/JPH02131462A/ja active Pending
-
1990
- 1990-11-08 HK HK926/90A patent/HK92690A/en not_active IP Right Cessation
-
1991
- 1991-12-20 CS CS913999A patent/CS399991A3/cs unknown
-
1992
- 1992-06-26 MX MX9203451A patent/MX9203451A/es unknown
-
1995
- 1995-11-27 NL NL950029C patent/NL950029I2/nl unknown
-
1996
- 1996-12-10 NO NO1996014C patent/NO1996014I1/no unknown
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