JP2017516862A5 - - Google Patents
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- JP2017516862A5 JP2017516862A5 JP2017515034A JP2017515034A JP2017516862A5 JP 2017516862 A5 JP2017516862 A5 JP 2017516862A5 JP 2017515034 A JP2017515034 A JP 2017515034A JP 2017515034 A JP2017515034 A JP 2017515034A JP 2017516862 A5 JP2017516862 A5 JP 2017516862A5
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- Prior art keywords
- haloalkyl
- item
- compound according
- alkyl
- compound
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 54
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 36
- 102000001307 androgen receptors Human genes 0.000 claims description 16
- 108010080146 androgen receptors Proteins 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- -1 t-butoxy Chemical group 0.000 claims description 10
- 229940124597 therapeutic agent Drugs 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 8
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 description 14
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 14
- 238000000034 method Methods 0.000 description 12
- 208000002874 Acne Vulgaris Diseases 0.000 description 4
- 201000004384 Alopecia Diseases 0.000 description 4
- 206010005003 Bladder cancer Diseases 0.000 description 4
- 206010006187 Breast cancer Diseases 0.000 description 4
- 208000026310 Breast neoplasm Diseases 0.000 description 4
- 206010014733 Endometrial cancer Diseases 0.000 description 4
- 206010014759 Endometrial neoplasm Diseases 0.000 description 4
- 206010020112 Hirsutism Diseases 0.000 description 4
- 208000008839 Kidney Neoplasms Diseases 0.000 description 4
- 206010033128 Ovarian cancer Diseases 0.000 description 4
- 206010061535 Ovarian neoplasm Diseases 0.000 description 4
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 4
- 206010038389 Renal cancer Diseases 0.000 description 4
- 208000004337 Salivary Gland Neoplasms Diseases 0.000 description 4
- 206010061934 Salivary gland cancer Diseases 0.000 description 4
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 description 4
- 206010000496 acne Diseases 0.000 description 4
- 206010064930 age-related macular degeneration Diseases 0.000 description 4
- 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 description 4
- 229960001573 cabazitaxel Drugs 0.000 description 4
- 208000024963 hair loss Diseases 0.000 description 4
- 230000003676 hair loss Effects 0.000 description 4
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 4
- 231100000844 hepatocellular carcinoma Toxicity 0.000 description 4
- 229960005386 ipilimumab Drugs 0.000 description 4
- 201000010982 kidney cancer Diseases 0.000 description 4
- 201000007270 liver cancer Diseases 0.000 description 4
- 208000014018 liver neoplasm Diseases 0.000 description 4
- 208000002780 macular degeneration Diseases 0.000 description 4
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 4
- 201000002528 pancreatic cancer Diseases 0.000 description 4
- 208000008443 pancreatic carcinoma Diseases 0.000 description 4
- 230000001568 sexual effect Effects 0.000 description 4
- 208000002320 spinal muscular atrophy Diseases 0.000 description 4
- 201000005112 urinary bladder cancer Diseases 0.000 description 4
- 206010036590 Premature baby Diseases 0.000 description 3
- 208000025661 ovarian cyst Diseases 0.000 description 3
- 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 description 2
- 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 description 2
- 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 description 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 229960000853 abiraterone Drugs 0.000 description 2
- 239000003098 androgen Substances 0.000 description 2
- 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 description 2
- 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 description 2
- 229940120638 avastin Drugs 0.000 description 2
- 229960000397 bevacizumab Drugs 0.000 description 2
- 229960000997 bicalutamide Drugs 0.000 description 2
- 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 description 2
- 229960000978 cyproterone acetate Drugs 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229960003668 docetaxel Drugs 0.000 description 2
- 229960004199 dutasteride Drugs 0.000 description 2
- 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 description 2
- WXCXUHSOUPDCQV-UHFFFAOYSA-N enzalutamide Chemical group 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 description 2
- 229960004671 enzalutamide Drugs 0.000 description 2
- 229960004039 finasteride Drugs 0.000 description 2
- 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 description 2
- 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 2
- 229960002074 flutamide Drugs 0.000 description 2
- 229950003400 galeterone Drugs 0.000 description 2
- 229950004319 izonsteride Drugs 0.000 description 2
- BLIJXOOIHRSQRB-PXYINDEMSA-N n-[(2s)-1-[3-(3-chloro-4-cyanophenyl)pyrazol-1-yl]propan-2-yl]-5-(1-hydroxyethyl)-1h-pyrazole-3-carboxamide Chemical compound C([C@H](C)NC(=O)C=1NN=C(C=1)C(C)O)N(N=1)C=CC=1C1=CC=C(C#N)C(Cl)=C1 BLIJXOOIHRSQRB-PXYINDEMSA-N 0.000 description 2
- 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 description 2
- 229960002653 nilutamide Drugs 0.000 description 2
- 208000015124 ovarian disease Diseases 0.000 description 2
- 201000010065 polycystic ovary syndrome Diseases 0.000 description 2
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 2
- 229960004618 prednisone Drugs 0.000 description 2
- 229910052705 radium Inorganic materials 0.000 description 2
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 229950007816 turosteride Drugs 0.000 description 2
- 150000001721 carbon Chemical class 0.000 description 1
- 208000031513 cyst Diseases 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2020089519A JP6925481B2 (ja) | 2014-05-30 | 2020-05-22 | アンドロゲン受容体調節物質及びその使用方法 |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462005714P | 2014-05-30 | 2014-05-30 | |
| US62/005,714 | 2014-05-30 | ||
| PCT/US2015/033385 WO2015184393A1 (en) | 2014-05-30 | 2015-05-29 | Androgen receptor modulators and methods for their use |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020089519A Division JP6925481B2 (ja) | 2014-05-30 | 2020-05-22 | アンドロゲン受容体調節物質及びその使用方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2017516862A JP2017516862A (ja) | 2017-06-22 |
| JP2017516862A5 true JP2017516862A5 (cg-RX-API-DMAC7.html) | 2018-07-05 |
Family
ID=53373659
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017515034A Pending JP2017516862A (ja) | 2014-05-30 | 2015-05-29 | アンドロゲン受容体調節物質及びその使用方法 |
| JP2020089519A Active JP6925481B2 (ja) | 2014-05-30 | 2020-05-22 | アンドロゲン受容体調節物質及びその使用方法 |
| JP2021127354A Pending JP2021176908A (ja) | 2014-05-30 | 2021-08-03 | アンドロゲン受容体調節物質及びその使用方法 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020089519A Active JP6925481B2 (ja) | 2014-05-30 | 2020-05-22 | アンドロゲン受容体調節物質及びその使用方法 |
| JP2021127354A Pending JP2021176908A (ja) | 2014-05-30 | 2021-08-03 | アンドロゲン受容体調節物質及びその使用方法 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US9682933B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3148970B1 (cg-RX-API-DMAC7.html) |
| JP (3) | JP2017516862A (cg-RX-API-DMAC7.html) |
| AU (3) | AU2015266654A1 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2948643C (cg-RX-API-DMAC7.html) |
| IL (1) | IL249203B (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ726348A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2015184393A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9487479B2 (en) * | 2008-08-22 | 2016-11-08 | The University Of British Columbia | Small molecule inhibitors of N-terminus activation of the androgen receptor |
| AU2015266654A1 (en) | 2014-05-30 | 2016-12-01 | British Columbia Cancer Agency Branch | Androgen receptor modulators and methods for their use |
| TWI726969B (zh) | 2016-01-11 | 2021-05-11 | 比利時商健生藥品公司 | 用作雄性激素受體拮抗劑之經取代之硫尿囊素衍生物 |
| JP2021517119A (ja) * | 2018-03-05 | 2021-07-15 | クリニクム レヒツ デア イザール デア テクニシェン ウニフェルジテート ミュンヘン | 腫瘍溶解性アデノウイルスとｃｄｋ４／６阻害剤との組み合わせによる腫瘍の処置 |
| WO2021021629A1 (en) * | 2019-07-26 | 2021-02-04 | University Of Florida Research Foundation, Incorporated | Discovery, total synthesis, and bioactivity of doscadenamides |
| WO2021044061A1 (en) * | 2019-09-05 | 2021-03-11 | Klinikum Rechts Der Isar Der Technischen Universität München | Treatment of tumors by a combination of an oncolytic adenovirus, a cdk4/6 inhibitor and a further therapeutically active agent |
| US12133846B2 (en) | 2019-10-15 | 2024-11-05 | Wayne State University | Electrophilic androgen receptor (AR) antagonists for AR downregulation and ferroptosis induction in cancer cells |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0317057A (ja) | 1989-06-15 | 1991-01-25 | Fujisawa Pharmaceut Co Ltd | 新規５員環複素環化合物 |
| AU4494399A (en) | 1998-06-30 | 2000-01-24 | University Of British Columbia, The | Inhibitors of androgen-independent activation of androgen receptor |
| US7772433B2 (en) | 2002-02-28 | 2010-08-10 | University Of Tennessee Research Foundation | SARMS and method of use thereof |
| EP1760076A1 (en) * | 2005-09-02 | 2007-03-07 | Ferring B.V. | FAP Inhibitors |
| US9487479B2 (en) | 2008-08-22 | 2016-11-08 | The University Of British Columbia | Small molecule inhibitors of N-terminus activation of the androgen receptor |
| AU2011312490B2 (en) * | 2010-09-28 | 2015-06-25 | Radius Pharmaceuticals, Inc. | Selective androgen receptor modulators |
| AU2015266654A1 (en) | 2014-05-30 | 2016-12-01 | British Columbia Cancer Agency Branch | Androgen receptor modulators and methods for their use |
-
2015
- 2015-05-29 AU AU2015266654A patent/AU2015266654A1/en not_active Abandoned
- 2015-05-29 EP EP15728354.0A patent/EP3148970B1/en active Active
- 2015-05-29 NZ NZ726348A patent/NZ726348A/en unknown
- 2015-05-29 CA CA2948643A patent/CA2948643C/en active Active
- 2015-05-29 US US14/726,129 patent/US9682933B2/en active Active
- 2015-05-29 JP JP2017515034A patent/JP2017516862A/ja active Pending
- 2015-05-29 WO PCT/US2015/033385 patent/WO2015184393A1/en not_active Ceased
-
2016
- 2016-11-24 IL IL249203A patent/IL249203B/en active IP Right Grant
-
2017
- 2017-06-19 US US15/626,526 patent/US10071962B2/en active Active
-
2019
- 2019-10-31 AU AU2019257509A patent/AU2019257509B2/en not_active Ceased
-
2020
- 2020-05-22 JP JP2020089519A patent/JP6925481B2/ja active Active
-
2021
- 2021-08-03 JP JP2021127354A patent/JP2021176908A/ja active Pending
- 2021-08-10 AU AU2021215137A patent/AU2021215137A1/en not_active Abandoned
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