JP2019513795A5 - - Google Patents
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- JP2019513795A5 JP2019513795A5 JP2018554381A JP2018554381A JP2019513795A5 JP 2019513795 A5 JP2019513795 A5 JP 2019513795A5 JP 2018554381 A JP2018554381 A JP 2018554381A JP 2018554381 A JP2018554381 A JP 2018554381A JP 2019513795 A5 JP2019513795 A5 JP 2019513795A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- pharmaceutically acceptable
- stereoisomer
- tautomer
- acceptable salt
- 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 94
- 150000003839 salts Chemical class 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 206010060862 Prostate cancer Diseases 0.000 claims description 26
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 26
- 229910052794 bromium Inorganic materials 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 108010080146 androgen receptors Proteins 0.000 claims description 18
- 102000001307 androgen receptors Human genes 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 15
- 229910052740 iodine Inorganic materials 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 229940124597 therapeutic agent Drugs 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
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- 208000004337 Salivary Gland Neoplasms Diseases 0.000 claims description 4
- 206010061934 Salivary gland cancer Diseases 0.000 claims description 4
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 4
- 206010000496 acne Diseases 0.000 claims description 4
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 4
- 231100000360 alopecia Toxicity 0.000 claims description 4
- 230000037444 atrophy Effects 0.000 claims 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 claims description 4
- 229960001573 cabazitaxel Drugs 0.000 claims description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 4
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
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- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
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- 201000005112 urinary bladder cancer Diseases 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 3
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 3
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 3
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 3
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims description 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
- 229930192474 thiophene Natural products 0.000 claims description 3
- 150000003852 triazoles Chemical class 0.000 claims 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 claims 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 claims 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 claims description 2
- 108091008715 AR-FL Proteins 0.000 claims 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 claims description 2
- CIGRGLYYGIMTOD-GOSISDBHSA-N N1(C=NC=C1)C1=C[C@H](C(CC1)(C)C)N(C1=CC(=C(C#N)C=C1)C(F)(F)F)C Chemical compound N1(C=NC=C1)C1=C[C@H](C(CC1)(C)C)N(C1=CC(=C(C#N)C=C1)C(F)(F)F)C CIGRGLYYGIMTOD-GOSISDBHSA-N 0.000 claims description 2
- 229960000853 abiraterone Drugs 0.000 claims 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 claims 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 claims description 2
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6884100B2 (ja) | 2015-01-13 | 2021-06-09 | ブリティッシュ コロンビア キャンサー エージェンシー ブランチ | がんの画像化及び治療用のヘテロ環式化合物ならびにそれらの使用方法 |
| US10471023B2 (en) | 2015-03-12 | 2019-11-12 | British Columbia Cancer Agency Branch | Bisphenol ether derivatives and methods for using the same |
| 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 |
| WO2019226991A1 (en) | 2018-05-25 | 2019-11-28 | Essa Pharma, Inc. | Androgen receptor modulators and methods for their use |
| MX2021004427A (es) | 2018-10-18 | 2021-11-12 | Univ British Columbia | Moduladores del receptor de andrógenos y métodos para su uso. |
| CN114502539A (zh) * | 2019-03-28 | 2022-05-13 | 埃萨制药股份有限公司 | 包含雄激素受体的抑制剂的药物组合物和组合及其用途 |
| WO2020198712A1 (en) * | 2019-03-28 | 2020-10-01 | Essa Pharma, Inc. | Pharmaceutical compositions and combinations comprising inhibitors of the androgen receptor and uses thereof |
| CN118085015A (zh) * | 2019-09-06 | 2024-05-28 | 江西济民可信集团有限公司 | 作为蛋白降解剂的并环类化合物及其制备方法和用途 |
| AU2021255723A1 (en) | 2020-04-17 | 2022-12-08 | Essa Pharma, Inc. | Solid forms of an N-terminal domain androgen receptor inhibitor and uses thereof |
| EP4023649A1 (en) | 2020-12-30 | 2022-07-06 | Industrial Technology Research Institute | Androgen receptor binding bifunctional molecules |
| CN113648418B (zh) * | 2021-05-08 | 2022-08-05 | 南方医科大学 | Apelin-APJ抑制剂在制备治疗血睾屏障损伤药物中的应用 |
| KR20220157096A (ko) * | 2021-05-20 | 2022-11-29 | 연세대학교 산학협력단 | 암의 예방, 개선 또는 치료용 조성물 |
| KR20220157089A (ko) * | 2021-05-20 | 2022-11-29 | 연세대학교 산학협력단 | 암의 예방, 개선 또는 치료용 조성물 |
| WO2023046283A1 (en) | 2021-09-22 | 2023-03-30 | Fundació Institut De Recerca Biomèdica (Irb Barcelona) | Compounds and their use in a method for modulating ar (androgen receptor) transcriptional activity |
Family Cites Families (99)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2571217A (en) | 1951-10-16 | Horace s | ||
| US2890189A (en) | 1954-06-14 | 1959-06-09 | Johnson & Son Inc S C | Alkali soluble resins and compositions containing the same |
| US3074974A (en) * | 1957-12-06 | 1963-01-22 | Monsanto Chemicals | Method for the preparation of diglycidyl ether of tetrachlorobisphenol-a |
| US3162615A (en) | 1961-01-03 | 1964-12-22 | Dow Chemical Co | Polyesters from cyclic polyhaloalkane polyols and unsaturated dicarboxylic acids |
| FR1389005A (fr) | 1963-01-09 | 1965-02-12 | Bayer Ag | Procédé perfectionné pour durcir des polyépoxydes |
| SU638596A1 (ru) | 1975-09-01 | 1978-12-25 | Государственный Научно-Исследовательский И Проектный Институт Полимерных Клеев Им. Э.Л.Тер-Газаряна | Хлоргидриднное производное диаллилизоциануровой кислоты в качестве пластификатора поливинилацетатной эмульсии |
| US4284574A (en) | 1979-06-15 | 1981-08-18 | Ciba-Geigy Corporation | Diglycidyl ethers of di-secondary alcohols, their preparation, and curable compositions containing them |
| SU929630A1 (ru) * | 1980-02-06 | 1982-05-23 | Научно-Исследовательский Институт Биологии При Иркутском Государственном Университете Им.А.А.Жданова | Способ получени ди-или триоксидифенил-сульфонов |
| US4369298A (en) | 1980-05-27 | 1983-01-18 | Tokuyama Soda Kabushiki Kaisha | Novel cured resin, process for production thereof, and lens composed of said resin from bis(alkyleneoxyphenyl)-diacrylate, bis(alkyleneoxyphenyl)diallyl ether, bis(alkyleneoxyphenyl)diallyl carbonate monomers |
| EP0056175B1 (en) | 1981-01-13 | 1985-05-02 | Teijin Limited | Ion-permeable composite membrane and its use in selective separation |
| IN169231B (https=) * | 1984-03-15 | 1991-09-14 | Ciba Geigy Ag | |
| PL141793B1 (en) | 1984-10-08 | 1987-08-31 | Politechnika Warszawska | Method of obtaining bisphenolic resins |
| US5753730A (en) | 1986-12-15 | 1998-05-19 | Mitsui Toatsu Chemicals, Inc. | Plastic lenses having a high-refractive index, process for the preparation thereof and casting polymerization process for preparing sulfur-containing urethane resin lens and lens prepared thereby |
| JPH0832844B2 (ja) | 1987-02-09 | 1996-03-29 | パイロツトインキ株式会社 | 筆記板用不透明性インキ |
| DE3852839T2 (de) | 1987-04-27 | 1995-06-22 | Mitsubishi Gas Chemical Co | Hitzehärtbare Harzzusammensetzung. |
| US5155196A (en) | 1987-06-01 | 1992-10-13 | The Dow Chemical Company | Polymer resulting from the cure of a preformed chromene-containing mixture |
| WO1988009782A1 (en) | 1987-06-01 | 1988-12-15 | The Dow Chemical Company | Process for making propargyl ethers of hydroxyaromatic compounds |
| JP2572020B2 (ja) * | 1987-06-19 | 1997-01-16 | 竹本油脂株式会社 | 熱硬化性樹脂用難燃剤 |
| DE3821585A1 (de) | 1987-09-13 | 1989-03-23 | Hoechst Ag | Positiv arbeitendes strahlungsempfindliches gemisch und daraus hergestelltes strahlungsempfindliches aufzeichnungsmaterial fuer hochenergetische strahlung |
| US4855184A (en) | 1988-02-02 | 1989-08-08 | Minnesota Mining And Manufacturing Company | Radiation-curable protective coating composition |
| DE3939760A1 (de) | 1989-12-01 | 1991-06-06 | Bayer Ag | Verfahren zur lackierung von kunststoffen, lackierte kunststoffe und die verwendung von hierzu geeigneten haftvermittlern |
| EP0515128A1 (en) | 1991-05-23 | 1992-11-25 | Konica Corporation | Silver halide color photographic light-sensitive material |
| JPH0649473A (ja) | 1992-08-04 | 1994-02-22 | Asahi Chem Ind Co Ltd | 冷媒組成物 |
| DE4323512A1 (de) | 1992-09-01 | 1994-04-28 | Agfa Gevaert Ag | Fotografisches Aufzeichnungsmaterial |
| JPH07117349A (ja) | 1993-10-27 | 1995-05-09 | Asahi Denka Kogyo Kk | 感熱記録材料 |
| CN1167437A (zh) | 1994-11-29 | 1997-12-10 | 赫彻斯特马里恩鲁斯公司 | 用三芳基-乙烯衍生物治疗和预防骨质疏松的方法 |
| DE19526146A1 (de) | 1995-07-07 | 1997-01-09 | Schering Ag | Triphenylethylene, Verfahren zu deren Herstellung, diese Triphenylethylene enthaltene pharmazeutische Präparate sowie deren Verwendung zur Herstellung von Arzneimitteln |
| JPH09176240A (ja) | 1995-12-27 | 1997-07-08 | Mitsubishi Chem Corp | 光重合性組成物 |
| JPH10133427A (ja) | 1996-11-05 | 1998-05-22 | Fuji Xerox Co Ltd | 静電潜像現像用キャリア、静電潜像現像剤及び画像形成方法 |
| ZA98900B (en) | 1997-02-07 | 1998-08-03 | Shell Int Research | Process for the manufacture of epoxy compounds |
| JPH10316803A (ja) | 1997-05-16 | 1998-12-02 | Teijin Chem Ltd | 難燃性樹脂組成物 |
| IL125840A (en) | 1997-08-22 | 2002-12-01 | Teijin Chemicals Ltd | Bromine compound production method |
| JPH11166087A (ja) | 1997-12-04 | 1999-06-22 | Teijin Chem Ltd | 難燃性樹脂組成物 |
| AU4494399A (en) | 1998-06-30 | 2000-01-24 | University Of British Columbia, The | Inhibitors of androgen-independent activation of androgen receptor |
| US6245117B1 (en) | 1998-08-07 | 2001-06-12 | Ipposha Oil Industries Co., Ltd. | Modifier of cellulose fibers and modification method of cellulose fibers |
| US6218430B1 (en) | 1998-08-24 | 2001-04-17 | Ligand Pharmaceuticals Incorporated | Vitamin D3 mimics |
| JP3795679B2 (ja) | 1998-09-01 | 2006-07-12 | 帝人化成株式会社 | 臭素化合物の製造方法 |
| AU775928B2 (en) | 1999-10-14 | 2004-08-19 | Bristol-Myers Squibb Company | Crystallographic structure of the androgen receptor ligand binding domain |
| US6534621B2 (en) | 2000-05-18 | 2003-03-18 | Dow Global Technologies Inc. | Process for manufacturing a hydroxyester derivative intermediate and epoxy resins prepared therefrom |
| US6472436B1 (en) | 2000-07-17 | 2002-10-29 | The Salk Institute For Biological Studies | Methods for protecting cells from amyloid toxicity and for inhibiting amyloid protein production |
| US6756400B2 (en) | 2000-08-31 | 2004-06-29 | Theravance, Inc. | Sodium channel modulators |
| US6646102B2 (en) | 2001-07-05 | 2003-11-11 | Dow Global Technologies Inc. | Process for manufacturing an alpha-dihydroxy derivative and epoxy resins prepared therefrom |
| US20030092724A1 (en) | 2001-09-18 | 2003-05-15 | Huaihung Kao | Combination sustained release-immediate release oral dosage forms with an opioid analgesic and a non-opioid analgesic |
| 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 |
| GEP20074191B (en) | 2002-06-17 | 2007-09-10 | Univ Tennessee Res Foundation | N-bridged selective androgen receptor modulators and methods of use thereof |
| GB0324551D0 (en) | 2003-10-21 | 2003-11-26 | Karobio Ab | Novel compounds |
| US7595345B2 (en) | 2003-11-20 | 2009-09-29 | Eli Lilly And Company | Vitamin D receptor modulators |
| CA2555597C (en) | 2004-02-13 | 2016-06-14 | The University Of British Columbia | Radiolabeled compounds and compositions, their precursors and methods for their production |
| JP2005325301A (ja) | 2004-05-17 | 2005-11-24 | Fuji Photo Film Co Ltd | セルロースアシレートドープ組成物、およびセルロースアシレートフィルム |
| EP1781280A2 (en) | 2004-08-18 | 2007-05-09 | Warner-Lambert Company LLC | Androgen modulators |
| JP2006208607A (ja) | 2005-01-26 | 2006-08-10 | Fuji Photo Film Co Ltd | パターン形成材料、並びにパターン形成装置及び永久パターン形成方法 |
| PT1861365E (pt) | 2005-03-15 | 2009-09-22 | 4Sc Ag | N-sulfonilpirroles e a sua utilização como inibidores de histona-desacetilase |
| JP4753601B2 (ja) | 2005-03-23 | 2011-08-24 | 旭化成イーマテリアルズ株式会社 | 感光性組成物 |
| EP1717235A3 (en) | 2005-04-29 | 2007-02-28 | Bioprojet | Phenoxypropylpiperidines and -pyrrolidines and their use as histamine H3-receptor ligands |
| FR2885904B1 (fr) | 2005-05-19 | 2007-07-06 | Aventis Pharma Sa | Nouveaux derives du fluorene, compositions les contenant et utilisation |
| EP1792622A1 (en) | 2005-11-11 | 2007-06-06 | GPC Biotech AG | Anti-proliferative combination therapy comprising a platinum-based chemotherapeutic agent and EGFR inhibitors or pyrimidine analogues |
| WO2007079078A1 (en) | 2005-12-29 | 2007-07-12 | Bayer Schering Pharma Aktiengesellschaft | Diamine derivatives as inhibitors of leukotriene a4 hydrolase |
| LT2656842T (lt) | 2006-03-27 | 2016-09-26 | The Regents Of The University Of California | Androgeno receptoriaus moduliatorius, skirtas prostatos vėžio ir su androgeno receptoriumi susijusių ligų gydymui |
| JP2007290980A (ja) | 2006-04-21 | 2007-11-08 | Shin Etsu Chem Co Ltd | 含フッ素（メタ）アクリル酸エステル |
| DE102006019044A1 (de) * | 2006-04-25 | 2007-10-31 | Merck Patent Gmbh | Antioxidantien |
| TW200819421A (en) | 2006-10-31 | 2008-05-01 | Univ Nat Chunghsing | The method of synthesizing biphenol A, BPA having di-alkoxyl group by using polycarbonate or its waste |
| KR20090115797A (ko) | 2007-02-20 | 2009-11-06 | 바스프 에스이 | 고굴절률 단량체, 이의 조성물 및 용도 |
| RU2572596C2 (ru) | 2008-07-02 | 2016-01-20 | Бритиш Коламбиа Кэнсер Эйдженси Бранч | Терапевтические средства на основе производных диглицилиловых простых эфиров и способы их применения |
| AU2009279936A1 (en) | 2008-08-05 | 2010-02-11 | Banyu Pharmaceutical Co., Ltd. | Therapeutic compounds |
| AR079975A1 (es) | 2010-01-06 | 2012-03-07 | British Columbia Cancer Agency | Agentes terapeuticos derivados de bisfenol u metodos para su uso, composiciones farmaceuticas y uso de los mismos |
| AR079846A1 (es) | 2010-01-06 | 2012-02-22 | British Columbia Cancer Agency | Agentes terapeuticos derivados de bisfenol que contienen un grupo aquiral y su uso en el tratamiento del cancer |
| WO2011103202A2 (en) | 2010-02-16 | 2011-08-25 | Aragon Pharmaceuticals, Inc. | Androgen receptor modulators and uses thereof |
| EP2693875A4 (en) | 2011-04-08 | 2014-10-22 | British Columbia Cancer Agency | BISPHENOL COMPOUNDS AND METHOD FOR THEIR USE |
| WO2012145328A1 (en) | 2011-04-18 | 2012-10-26 | The University Of British Columbia | Dibenzylphenyl compounds and methods for their use |
| WO2012145330A1 (en) | 2011-04-18 | 2012-10-26 | The University Of British Columbia | Fluorene-9-bisphenol compounds and methods for their use |
| WO2013028572A1 (en) | 2011-08-19 | 2013-02-28 | British Columbia Cancer Agency Branch | Fluorinated bisphenol ether compounds and methods for their use |
| WO2013028791A1 (en) | 2011-08-22 | 2013-02-28 | British Columbia Cancer Agency Branch | 18f compounds for cancer imaging and methods for their use |
| US9365510B2 (en) | 2012-04-16 | 2016-06-14 | British Columbia Cancer Agency Branch | Aziridine bisphenol ethers and related compounds and methods for their use |
| PT2872482T (pt) | 2012-07-13 | 2020-09-22 | Oncternal Therapeutics Inc | Método de tratamento de cancro de mama com modulador seletivo do recetor de andrógeno (sarm) |
| MA37975B2 (fr) | 2012-09-11 | 2021-03-31 | Genzyme Corp | Inhibiteurs de synthase de glucosylcéramide |
| CN105358522A (zh) | 2013-05-10 | 2016-02-24 | 不列颠哥伦比亚癌症局分支机构 | 雄激素受体调节剂的酯衍生物及其使用方法 |
| CN103342892A (zh) | 2013-06-06 | 2013-10-09 | 西安交通大学 | 一种双马来酰亚胺树脂的增韧改性剂及其制备方法 |
| US20150010469A1 (en) * | 2013-07-03 | 2015-01-08 | British Columbia Cancer Agency Branch | Bisphenol ether compounds with novel bridging groups and methods for their use |
| SG11201601431VA (en) | 2013-09-09 | 2016-03-30 | British Columbia Cancer Agency | Halogenated compounds for cancer imaging and treatment and methods for their use |
| TW201600499A (zh) | 2014-05-15 | 2016-01-01 | 巴斯夫歐洲公司 | 用於製備石墨烯奈米帶的鄰三聯苯 |
| WO2016058080A1 (en) | 2014-10-14 | 2016-04-21 | British Columbia Cancer Agency Branch | Fluoro-chloro bisphenol ether compounds and methods for their use |
| WO2016058082A1 (en) | 2014-10-14 | 2016-04-21 | British Columbia Cancer Agency Branch | 18f compounds for cancer imaging and methods for their use |
| JP6884100B2 (ja) * | 2015-01-13 | 2021-06-09 | ブリティッシュ コロンビア キャンサー エージェンシー ブランチ | がんの画像化及び治療用のヘテロ環式化合物ならびにそれらの使用方法 |
| US10471023B2 (en) | 2015-03-12 | 2019-11-12 | 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 |
| US10980806B2 (en) | 2016-03-24 | 2021-04-20 | University of Pittsburgh—of the Commonwealth System of Higher Education | Small molecule inhibitors of the nuclear translocation of androgen receptor 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 |
| WO2017210771A1 (en) | 2016-06-06 | 2017-12-14 | British Columbia Cancer Agency Branch | Compounds and compositions for radiation therapy and methods of using the same |
| LT3474841T (lt) | 2016-06-22 | 2022-06-10 | Ellipses Pharma Ltd | Ar+ krūties vėžio gydymo būdai |
| 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 |
| WO2019023651A2 (en) | 2017-07-28 | 2019-01-31 | Massachusetts Institute Of Technology | MODULATORS OF THE SMALL MOLECULE ANDROGEN RECEPTOR |
| WO2019226991A1 (en) | 2018-05-25 | 2019-11-28 | Essa Pharma, Inc. | Androgen receptor modulators and methods for their use |
| MX2021004427A (es) | 2018-10-18 | 2021-11-12 | Univ British Columbia | Moduladores del receptor de andrógenos y métodos para su uso. |
| CN113164500A (zh) | 2018-12-07 | 2021-07-23 | 大日本住友制药肿瘤公司 | 治疗去势抵抗性和去势敏感性前列腺癌的方法 |
| WO2020198712A1 (en) | 2019-03-28 | 2020-10-01 | Essa Pharma, Inc. | Pharmaceutical compositions and combinations comprising inhibitors of the androgen receptor and uses thereof |
| AU2020247255A1 (en) | 2019-03-28 | 2021-11-11 | Essa Pharma, Inc. | Androgen receptor modulators and methods for use as Proteolysis Targeting Chimera ligands |
| CN114502539A (zh) | 2019-03-28 | 2022-05-13 | 埃萨制药股份有限公司 | 包含雄激素受体的抑制剂的药物组合物和组合及其用途 |
| AU2021255723A1 (en) | 2020-04-17 | 2022-12-08 | Essa Pharma, Inc. | Solid forms of an N-terminal domain androgen receptor inhibitor and uses thereof |
| WO2022060969A1 (en) | 2020-09-16 | 2022-03-24 | Essa Pharma, Inc. | Pharmaceutical compositions and combinations comprising inhibitors of the androgen receptor and uses thereof |
-
2017
- 2017-04-17 US US15/489,162 patent/US20170298033A1/en not_active Abandoned
- 2017-04-18 MX MX2018012619A patent/MX392906B/es unknown
- 2017-04-18 EP EP17781660.0A patent/EP3442942B1/en active Active
- 2017-04-18 KR KR1020187033112A patent/KR102409651B1/ko not_active Expired - Fee Related
- 2017-04-18 CA CA3021008A patent/CA3021008A1/en active Pending
- 2017-04-18 NZ NZ748200A patent/NZ748200A/en not_active IP Right Cessation
- 2017-04-18 AU AU2017250025A patent/AU2017250025B2/en not_active Ceased
- 2017-04-18 RU RU2018140071A patent/RU2767257C2/ru active
- 2017-04-18 BR BR112018071183-7A patent/BR112018071183B1/pt not_active IP Right Cessation
- 2017-04-18 CN CN202410933269.9A patent/CN119143585A/zh active Pending
- 2017-04-18 ES ES17781660T patent/ES2969445T3/es active Active
- 2017-04-18 CN CN201780034942.3A patent/CN109311807B/zh not_active Expired - Fee Related
- 2017-04-18 WO PCT/CA2017/000083 patent/WO2017177307A1/en not_active Ceased
- 2017-04-18 JP JP2018554381A patent/JP7142577B2/ja active Active
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2018
- 2018-10-14 IL IL262338A patent/IL262338B/en unknown
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2020
- 2020-04-14 US US16/848,061 patent/US11142508B2/en active Active
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2021
- 2021-08-17 US US17/404,589 patent/US11919874B2/en active Active
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2022
- 2022-06-07 JP JP2022092370A patent/JP2022120018A/ja active Pending
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2024
- 2024-10-17 US US18/918,840 patent/US20250100986A1/en not_active Abandoned
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