JP2016518394A5 - - Google Patents
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- JP2016518394A5 JP2016518394A5 JP2016512175A JP2016512175A JP2016518394A5 JP 2016518394 A5 JP2016518394 A5 JP 2016518394A5 JP 2016512175 A JP2016512175 A JP 2016512175A JP 2016512175 A JP2016512175 A JP 2016512175A JP 2016518394 A5 JP2016518394 A5 JP 2016518394A5
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- JP
- Japan
- Prior art keywords
- cancer
- disease
- compound
- condition
- prostate cancer
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 56
- 206010060862 Prostate cancer Diseases 0.000 claims description 27
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 27
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 102000001307 androgen receptors Human genes 0.000 claims description 15
- 108010080146 androgen receptors Proteins 0.000 claims description 15
- -1 6-cyano-5- (trifluoromethyl) pyridin-3-yl Chemical group 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 230000000694 effects Effects 0.000 claims description 10
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 8
- 201000004384 Alopecia Diseases 0.000 claims description 8
- 206010006187 Breast cancer Diseases 0.000 claims description 8
- 208000026310 Breast neoplasm Diseases 0.000 claims description 8
- 206010014733 Endometrial cancer Diseases 0.000 claims description 8
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 8
- 206010020112 Hirsutism Diseases 0.000 claims description 8
- 206010033128 Ovarian cancer Diseases 0.000 claims description 8
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 8
- 208000004337 Salivary Gland Neoplasms Diseases 0.000 claims description 8
- 206010061934 Salivary gland cancer Diseases 0.000 claims description 8
- 206010000496 acne Diseases 0.000 claims description 8
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 8
- 208000024963 hair loss Diseases 0.000 claims description 8
- 230000003676 hair loss Effects 0.000 claims description 8
- 208000002780 macular degeneration Diseases 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 208000025661 ovarian cyst Diseases 0.000 claims description 8
- 208000006155 precocious puberty Diseases 0.000 claims description 8
- 206010036049 Polycystic ovaries Diseases 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 7
- 229940124597 therapeutic agent Drugs 0.000 claims description 7
- BMQGVNUXMIRLCK-OAGWZNDDSA-N cabazitaxel Chemical compound O([C@H]1[C@@H]2[C@]3(OC(C)=O)CO[C@@H]3C[C@@H]([C@]2(C(=O)[C@H](OC)C2=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=3C=CC=CC=3)C[C@]1(O)C2(C)C)C)OC)C(=O)C1=CC=CC=C1 BMQGVNUXMIRLCK-OAGWZNDDSA-N 0.000 claims description 6
- 229960001573 cabazitaxel Drugs 0.000 claims description 6
- 201000000585 muscular atrophy Diseases 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- LAMIXXKAWNLXOC-INIZCTEOSA-N (S)-HDAC-42 Chemical compound O=C([C@@H](C(C)C)C=1C=CC=CC=1)NC1=CC=C(C(=O)NO)C=C1 LAMIXXKAWNLXOC-INIZCTEOSA-N 0.000 claims description 5
- 239000003098 androgen Substances 0.000 claims description 5
- 230000001419 dependent effect Effects 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 229960005386 ipilimumab Drugs 0.000 claims description 5
- FAIZUAWLKOHMOP-ZOIXLQFFSA-N (1s,3as,3bs,5ar,9ar,9bs,11as)-9a,11a-dimethyl-7-oxo-n-(1,1,1-trifluoro-2-phenylpropan-2-yl)-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide Chemical compound O=C([C@@H]1[C@]2(CC[C@@H]3[C@@]4(C)C=CC(=O)N[C@@H]4CC[C@H]3[C@@H]2CC1)C)NC(C)(C(F)(F)F)C1=CC=CC=C1 FAIZUAWLKOHMOP-ZOIXLQFFSA-N 0.000 claims description 4
- LKJPYSCBVHEWIU-KRWDZBQOSA-N (R)-bicalutamide Chemical compound C([C@@](O)(C)C(=O)NC=1C=C(C(C#N)=CC=1)C(F)(F)F)S(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-KRWDZBQOSA-N 0.000 claims description 3
- VMGWGDPZHXPFTC-HYBUGGRVSA-N Izonsteride Chemical compound CN([C@@H]1CCC2=C3)C(=O)CC[C@]1(C)C2=CC=C3SC(S1)=NC2=C1C=CC=C2CC VMGWGDPZHXPFTC-HYBUGGRVSA-N 0.000 claims description 3
- ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 3
- GZOSMCIZMLWJML-VJLLXTKPSA-N abiraterone Chemical compound C([C@H]1[C@H]2[C@@H]([C@]3(CC[C@H](O)CC3=CC2)C)CC[C@@]11C)C=C1C1=CC=CN=C1 GZOSMCIZMLWJML-VJLLXTKPSA-N 0.000 claims description 3
- 229960000853 abiraterone Drugs 0.000 claims description 3
- HJBWBFZLDZWPHF-UHFFFAOYSA-N apalutamide Chemical compound C1=C(F)C(C(=O)NC)=CC=C1N1C2(CCC2)C(=O)N(C=2C=C(C(C#N)=NC=2)C(F)(F)F)C1=S HJBWBFZLDZWPHF-UHFFFAOYSA-N 0.000 claims description 3
- 229960000397 bevacizumab Drugs 0.000 claims description 3
- 229960000997 bicalutamide Drugs 0.000 claims description 3
- UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 claims description 3
- 229960000978 cyproterone acetate Drugs 0.000 claims description 3
- 229960003668 docetaxel Drugs 0.000 claims description 3
- 229960004199 dutasteride Drugs 0.000 claims description 3
- JWJOTENAMICLJG-QWBYCMEYSA-N dutasteride Chemical compound O=C([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)N[C@@H]4CC3)C)CC[C@@]21C)NC1=CC(C(F)(F)F)=CC=C1C(F)(F)F JWJOTENAMICLJG-QWBYCMEYSA-N 0.000 claims description 3
- 229960004671 enzalutamide Drugs 0.000 claims description 3
- WXCXUHSOUPDCQV-UHFFFAOYSA-N enzalutamide Chemical compound C1=C(F)C(C(=O)NC)=CC=C1N1C(C)(C)C(=O)N(C=2C=C(C(C#N)=CC=2)C(F)(F)F)C1=S WXCXUHSOUPDCQV-UHFFFAOYSA-N 0.000 claims description 3
- 229960004039 finasteride Drugs 0.000 claims description 3
- DBEPLOCGEIEOCV-WSBQPABSSA-N finasteride Chemical compound N([C@@H]1CC2)C(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)NC(C)(C)C)[C@@]2(C)CC1 DBEPLOCGEIEOCV-WSBQPABSSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 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 claims description 3
- 229960002074 flutamide Drugs 0.000 claims description 3
- 229950004319 izonsteride Drugs 0.000 claims description 3
- XWXYUMMDTVBTOU-UHFFFAOYSA-N nilutamide Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 XWXYUMMDTVBTOU-UHFFFAOYSA-N 0.000 claims description 3
- 229960002653 nilutamide Drugs 0.000 claims description 3
- WMPQMBUXZHMEFZ-YJPJVVPASA-N turosteride Chemical compound CN([C@@H]1CC2)C(=O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)N(C(C)C)C(=O)NC(C)C)[C@@]2(C)CC1 WMPQMBUXZHMEFZ-YJPJVVPASA-N 0.000 claims description 3
- 229950007816 turosteride Drugs 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims 13
- UYOVRYGHWYJIGX-TXTPUJOMSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-2,7,8,9,11,12,14,15,16,17-decahydro-1h-cyclopenta[a]phenanthrene-3-carboxylic acid Chemical compound C1C=C2C=C(C(O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CCC[C@@]1(C)CC2 UYOVRYGHWYJIGX-TXTPUJOMSA-N 0.000 claims 2
- 206010003694 Atrophy Diseases 0.000 claims 2
- PAFKTGFSEFKSQG-PAASFTFBSA-N Galeterone Chemical compound C1=NC2=CC=CC=C2N1C1=CC[C@H]2[C@H](CC=C3[C@@]4(CC[C@H](O)C3)C)[C@@H]4CC[C@@]21C PAFKTGFSEFKSQG-PAASFTFBSA-N 0.000 claims 2
- 230000037444 atrophy Effects 0.000 claims 2
- 229950003400 galeterone Drugs 0.000 claims 2
- 102000006495 integrins Human genes 0.000 claims 2
- 108010044426 integrins Proteins 0.000 claims 2
- 229910052705 radium Inorganic materials 0.000 claims 2
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 claims 2
- 230000001568 sexual effect Effects 0.000 claims 2
- 230000002792 vascular Effects 0.000 claims 2
- WZQDSHZMIONMBH-UHFFFAOYSA-N 2h-quinoline-1-carboxamide Chemical compound C1=CC=C2N(C(=O)N)CC=CC2=C1 WZQDSHZMIONMBH-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- RMTMMKNSPRRFHW-SVAVBUBPSA-N apatorsen Chemical compound N1([C@@H]2O[C@H](COP(O)(=S)OC3C([C@@H](O[C@@H]3COP(O)(=S)OC3C([C@@H](O[C@@H]3COP(O)(=S)OC3C([C@@H](O[C@@H]3COP(O)(=S)OC3[C@H](O[C@H](C3)N3C4=C(C(NC(N)=N4)=O)N=C3)COP(O)(=S)OC3[C@H](O[C@H](C3)N3C4=C(C(NC(N)=N4)=O)N=C3)COP(O)(=S)OC3[C@H](O[C@H](C3)N3C(N=C(N)C(C)=C3)=O)COP(O)(=S)OC3[C@H](O[C@H](C3)N3C(NC(=O)C(C)=C3)=O)COP(O)(=S)OC3[C@H](O[C@H](C3)N3C(N=C(N)C(C)=C3)=O)COP(O)(=S)OC3[C@H](O[C@H](C3)N3C4=C(C(NC(N)=N4)=O)N=C3)COP(O)(=S)OC3[C@H](O[C@H](C3)N3C(N=C(N)C(C)=C3)=O)COP(O)(=S)OC3[C@H](O[C@H](C3)N3C4=C(C(NC(N)=N4)=O)N=C3)COP(O)(=S)OC3[C@H](O[C@H](C3)N3C4=C(C(NC(N)=N4)=O)N=C3)COP(O)(=S)OC3[C@H](O[C@H](C3)N3C(N=C(N)C(C)=C3)=O)COP(S)(=O)OC3[C@H](O[C@H](C3)N3C4=C(C(NC(N)=N4)=O)N=C3)COP(O)(=S)OC3[C@H](O[C@H](C3)N3C(N=C(N)C(C)=C3)=O)COP(O)(=S)OC3C([C@@H](O[C@@H]3COP(O)(=S)OC3C([C@@H](O[C@@H]3COP(O)(=S)OC3C([C@@H](O[C@@H]3COP(O)(=S)OC3C([C@@H](O[C@@H]3CO)N3C4=C(C(NC(N)=N4)=O)N=C3)OCCOC)N3C4=C(C(NC(N)=N4)=O)N=C3)OCCOC)N3C4=C(C(NC(N)=N4)=O)N=C3)OCCOC)N3C4=NC=NC(N)=C4N=C3)OCCOC)N3C(NC(=O)C(C)=C3)=O)OCCOC)N3C(N=C(N)C(C)=C3)=O)OCCOC)N3C4=C(C(NC=N4)=N)N=C3)OCCOC)C(O)C2OCCOC)C=C(C)C(=O)NC1=O RMTMMKNSPRRFHW-SVAVBUBPSA-N 0.000 claims 1
- 229950002986 apatorsen Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 description 12
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 9
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 6
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- 0 CC(*[C@@](COC(C)=O)COc1ccc(Cc(cc2)ccc2OCC(C*)O)cc1)=O Chemical compound CC(*[C@@](COC(C)=O)COc1ccc(Cc(cc2)ccc2OCC(C*)O)cc1)=O 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- RCOCFQYYXFCMMQ-UHFFFAOYSA-N CC(C)(C(CC1)=CC=C1OCC(CCl)OC(C)=O)c(cc1)ccc1OCC(COC(C)=O)O Chemical compound CC(C)(C(CC1)=CC=C1OCC(CCl)OC(C)=O)c(cc1)ccc1OCC(COC(C)=O)O RCOCFQYYXFCMMQ-UHFFFAOYSA-N 0.000 description 1
- CLJWBGBUDDUCLZ-UHFFFAOYSA-N CC(C)(c(cc1)ccc1OCC(CCl)O)c(cc1)ccc1OCC(COC(C)=O)OC(C)=O Chemical compound CC(C)(c(cc1)ccc1OCC(CCl)O)c(cc1)ccc1OCC(COC(C)=O)OC(C)=O CLJWBGBUDDUCLZ-UHFFFAOYSA-N 0.000 description 1
- RKDOKWLUDXJNBJ-UGKGYDQZSA-N CC(C)(c(cc1)ccc1OC[C@H](CO)O)c(cc1)ccc1OC[C@H](CCl)OC(C)=O Chemical compound CC(C)(c(cc1)ccc1OC[C@H](CO)O)c(cc1)ccc1OC[C@H](CCl)OC(C)=O RKDOKWLUDXJNBJ-UGKGYDQZSA-N 0.000 description 1
- AJTMESOWZFEOTR-XUZZJYLKSA-N CC(C)(c(cc1)ccc1OC[C@H](COC(C)=O)O)c(cc1)ccc1OC[C@@H](CCl)OC(C)=O Chemical compound CC(C)(c(cc1)ccc1OC[C@H](COC(C)=O)O)c(cc1)ccc1OC[C@@H](CCl)OC(C)=O AJTMESOWZFEOTR-XUZZJYLKSA-N 0.000 description 1
- SOUMGHPKQSVWED-PKNKJROBSA-O CC(O)O[C@@H](COc1ccc(C(C)(C)c(cc2)ccc2OCC(C[OH2+])OCC(O[C@@H](COc2ccc(C(C)(C)c(cc3)ccc3OC[C@H](CO)O)cc2)CCl)=O)cc1)CCl Chemical compound CC(O)O[C@@H](COc1ccc(C(C)(C)c(cc2)ccc2OCC(C[OH2+])OCC(O[C@@H](COc2ccc(C(C)(C)c(cc3)ccc3OC[C@H](CO)O)cc2)CCl)=O)cc1)CCl SOUMGHPKQSVWED-PKNKJROBSA-O 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 0.000 description 1
- 229940120638 avastin Drugs 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000005345 deuteroalkyl group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000849 selective androgen receptor modulator Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 125000000165 tricyclic carbocycle group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361822186P | 2013-05-10 | 2013-05-10 | |
| US61/822,186 | 2013-05-10 | ||
| PCT/CA2014/000414 WO2014179867A1 (en) | 2013-05-10 | 2014-05-09 | Ester derivatives of androgen receptor modulators and methods for their use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017031228A Division JP2017125036A (ja) | 2013-05-10 | 2017-02-22 | アンドロゲン受容体調節薬のエステル誘導体およびそれらの使用のための方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016518394A JP2016518394A (ja) | 2016-06-23 |
| JP2016518394A5 true JP2016518394A5 (https=) | 2016-08-04 |
| JP6100439B2 JP6100439B2 (ja) | 2017-03-22 |
Family
ID=51864937
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016512175A Expired - Fee Related JP6100439B2 (ja) | 2013-05-10 | 2014-05-09 | アンドロゲン受容体調節薬のエステル誘導体およびそれらの使用のための方法 |
| JP2017031228A Pending JP2017125036A (ja) | 2013-05-10 | 2017-02-22 | アンドロゲン受容体調節薬のエステル誘導体およびそれらの使用のための方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017031228A Pending JP2017125036A (ja) | 2013-05-10 | 2017-02-22 | アンドロゲン受容体調節薬のエステル誘導体およびそれらの使用のための方法 |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US9173939B2 (https=) |
| EP (1) | EP2994451A4 (https=) |
| JP (2) | JP6100439B2 (https=) |
| KR (2) | KR20170060162A (https=) |
| CN (1) | CN105358522A (https=) |
| AP (1) | AP2015008838A0 (https=) |
| AU (2) | AU2014262333B2 (https=) |
| BR (1) | BR112015028174A2 (https=) |
| CA (1) | CA2911352A1 (https=) |
| CL (1) | CL2015003271A1 (https=) |
| HK (1) | HK1221712A1 (https=) |
| IL (1) | IL242345A (https=) |
| MX (1) | MX347705B (https=) |
| PE (1) | PE20160091A1 (https=) |
| PH (2) | PH12015502525A1 (https=) |
| SG (2) | SG11201509038UA (https=) |
| WO (1) | WO2014179867A1 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE034458T2 (en) | 2008-07-02 | 2018-02-28 | British Columbia Cancer Agency Branch | Diglycidyl ether derivatives, therapeutics and methods for their use |
| US9388112B2 (en) | 2010-01-06 | 2016-07-12 | The University Of British Columbia | Bisphenol derivatives and their use as androgen receptor activity modulators |
| US9365510B2 (en) | 2012-04-16 | 2016-06-14 | British Columbia Cancer Agency Branch | Aziridine bisphenol ethers and related compounds and methods for their use |
| AU2014262333B2 (en) | 2013-05-10 | 2016-06-16 | British Columbia Cancer Agency Branch | Ester derivatives of androgen receptor modulators and methods for their use |
| WO2015031984A1 (en) | 2013-09-09 | 2015-03-12 | British Columbia Cancer Agency Branch | Halogenated compounds for cancer imaging and treatment and methods for their use |
| DK3988541T3 (da) | 2015-01-13 | 2024-09-16 | British Columbia Cancer Agency Branch | Heterocycliske forbindelser til billedscanning og behandling af cancer samt fremgangsmåder til anvendelse af disse |
| WO2016141458A1 (en) * | 2015-03-12 | 2016-09-15 | British Columbia Cancer Agency Branch | Bisphenol ether derivatives and methods for using the same |
| CA2929345A1 (en) * | 2015-09-02 | 2017-03-02 | British Columbia Cancer Agency Branch | Co-targeting androgen receptor splice variants and mtor signaling pathway for the treatment of castration-resistant prostate cancer |
| US20170298033A1 (en) * | 2016-04-15 | 2017-10-19 | The University Of British Columbia | Bisphenol derivatives and their use as androgen receptor activity modulators |
| WO2018045450A1 (en) * | 2016-09-09 | 2018-03-15 | British Columbia Cancer Agency Branch | Bisphenol a compounds and methods for treating drug-resistant androgen receptor mediated cancers |
| KR102368555B1 (ko) * | 2016-12-16 | 2022-02-28 | 강푸 바이오파마슈티칼즈 리미티드 | 조성물, 이의 적용 및 치료 방법 |
| WO2018157232A1 (en) * | 2017-02-28 | 2018-09-07 | British Columbia Cancer Agency Branch | Pharmaceutical compositions 'and combinations comprising inhibitors of the androgen receptor a1wd uses thereof |
| US11485713B2 (en) | 2018-05-25 | 2022-11-01 | Essa Pharma, Inc. | Androgen receptor modulators and methods for their use |
| WO2020081999A1 (en) | 2018-10-18 | 2020-04-23 | Essa Pharma, Inc. | Androgen receptor modulators and methods for their use |
| WO2020198712A1 (en) * | 2019-03-28 | 2020-10-01 | Essa Pharma, Inc. | Pharmaceutical compositions and combinations comprising inhibitors of the androgen receptor and uses thereof |
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-
2014
- 2014-05-09 AU AU2014262333A patent/AU2014262333B2/en not_active Ceased
- 2014-05-09 KR KR1020177013536A patent/KR20170060162A/ko not_active Withdrawn
- 2014-05-09 CA CA2911352A patent/CA2911352A1/en not_active Abandoned
- 2014-05-09 AP AP2015008838A patent/AP2015008838A0/xx unknown
- 2014-05-09 PE PE2015002373A patent/PE20160091A1/es not_active Application Discontinuation
- 2014-05-09 EP EP14793978.9A patent/EP2994451A4/en not_active Withdrawn
- 2014-05-09 WO PCT/CA2014/000414 patent/WO2014179867A1/en not_active Ceased
- 2014-05-09 MX MX2015015509A patent/MX347705B/es active IP Right Grant
- 2014-05-09 SG SG11201509038UA patent/SG11201509038UA/en unknown
- 2014-05-09 BR BR112015028174A patent/BR112015028174A2/pt not_active Application Discontinuation
- 2014-05-09 JP JP2016512175A patent/JP6100439B2/ja not_active Expired - Fee Related
- 2014-05-09 CN CN201480026227.1A patent/CN105358522A/zh active Pending
- 2014-05-09 US US14/274,528 patent/US9173939B2/en not_active Expired - Fee Related
- 2014-05-09 SG SG10201607177XA patent/SG10201607177XA/en unknown
- 2014-05-09 KR KR1020157035129A patent/KR101739800B1/ko not_active Expired - Fee Related
- 2014-05-09 HK HK16109321.3A patent/HK1221712A1/zh unknown
-
2015
- 2015-09-03 US US14/844,788 patent/US20160068466A1/en not_active Abandoned
- 2015-10-29 IL IL242345A patent/IL242345A/en not_active IP Right Cessation
- 2015-11-04 PH PH12015502525A patent/PH12015502525A1/en unknown
- 2015-11-06 CL CL2015003271A patent/CL2015003271A1/es unknown
-
2016
- 2016-06-02 PH PH12016501047A patent/PH12016501047A1/en unknown
- 2016-09-15 AU AU2016228233A patent/AU2016228233A1/en not_active Abandoned
-
2017
- 2017-02-22 JP JP2017031228A patent/JP2017125036A/ja active Pending
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