JP2018502867A5 - - Google Patents
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- JP2018502867A5 JP2018502867A5 JP2017536829A JP2017536829A JP2018502867A5 JP 2018502867 A5 JP2018502867 A5 JP 2018502867A5 JP 2017536829 A JP2017536829 A JP 2017536829A JP 2017536829 A JP2017536829 A JP 2017536829A JP 2018502867 A5 JP2018502867 A5 JP 2018502867A5
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- JP
- Japan
- Prior art keywords
- cancer
- alkyl
- independently
- item
- compound according
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 229910052740 iodine Inorganic materials 0.000 claims description 22
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 20
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 206010060862 Prostate cancer Diseases 0.000 claims description 15
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 201000011510 cancer Diseases 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229940124597 therapeutic agent Drugs 0.000 claims description 6
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 5
- 201000004384 Alopecia Diseases 0.000 claims description 5
- 206010006187 Breast cancer Diseases 0.000 claims description 5
- 208000026310 Breast neoplasm Diseases 0.000 claims description 5
- 206010014733 Endometrial cancer Diseases 0.000 claims description 5
- 206010014759 Endometrial neoplasm Diseases 0.000 claims description 5
- 206010020112 Hirsutism Diseases 0.000 claims description 5
- 206010033128 Ovarian cancer Diseases 0.000 claims description 5
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
- 208000004337 Salivary Gland Neoplasms Diseases 0.000 claims description 5
- 206010061934 Salivary gland cancer Diseases 0.000 claims description 5
- 206010000496 acne Diseases 0.000 claims description 5
- 208000024963 hair loss Diseases 0.000 claims description 5
- 230000003676 hair loss Effects 0.000 claims description 5
- 238000003384 imaging method Methods 0.000 claims description 5
- 208000025661 ovarian cyst Diseases 0.000 claims description 5
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 5
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 206010064930 age-related macular degeneration Diseases 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 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
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 208000002780 macular degeneration Diseases 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000000165 tricyclic carbocycle group Chemical group 0.000 claims description 4
- 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
- 239000003098 androgen Substances 0.000 claims description 3
- 229960001573 cabazitaxel Drugs 0.000 claims description 3
- 230000001419 dependent effect Effects 0.000 claims description 3
- 229960003668 docetaxel Drugs 0.000 claims description 3
- 239000003937 drug carrier Substances 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
- 229960005386 ipilimumab Drugs 0.000 claims description 3
- 208000006155 precocious puberty Diseases 0.000 claims description 3
- 238000002603 single-photon emission computed tomography Methods 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
- WQBIOEFDDDEARX-CHWSQXEVSA-N (4ar,10br)-8-chloro-4-methyl-1,2,4a,5,6,10b-hexahydrobenzo[f]quinolin-3-one Chemical compound C1CC2=CC(Cl)=CC=C2[C@@H]2[C@@H]1N(C)C(=O)CC2 WQBIOEFDDDEARX-CHWSQXEVSA-N 0.000 claims description 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 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
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- CXWGKAYMVASWDQ-UHFFFAOYSA-N 1,2-dithiane Chemical compound C1CCSSC1 CXWGKAYMVASWDQ-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims description 2
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 206010028289 Muscle atrophy Diseases 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 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
- 229960000853 abiraterone Drugs 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
- 229940120638 avastin Drugs 0.000 claims description 2
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 2
- 229960000397 bevacizumab Drugs 0.000 claims description 2
- 229950008527 bexlosteride Drugs 0.000 claims description 2
- 229960000997 bicalutamide Drugs 0.000 claims description 2
- 229960000978 cyproterone acetate Drugs 0.000 claims 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 claims description 2
- LOZWAPSEEHRYPG-UHFFFAOYSA-N dithiane Natural products C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
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- 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 2
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- 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 claims description 2
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- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 2
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| 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 |
| EP2139878A2 (en) | 2007-02-20 | 2010-01-06 | Basf Se | High refractive index monomers, compositions and uses thereof |
| KR20110044216A (ko) | 2008-07-02 | 2011-04-28 | 브리티쉬 콜롬비아 캔써 에이전시 브랜치 | 디글리시드 에테르 유도체 치료법 및 이의 사용 방법 |
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| EP2693875A4 (en) * | 2011-04-08 | 2014-10-22 | British Columbia Cancer Agency | BISPHENOL COMPOUNDS AND METHOD 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 |
| WO2012145328A1 (en) | 2011-04-18 | 2012-10-26 | The University Of British Columbia | Dibenzylphenyl compounds and methods for their use |
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-
2016
- 2016-01-13 HU HUE16736999A patent/HUE057962T2/hu unknown
- 2016-01-13 PL PL21212648.6T patent/PL3988541T3/pl unknown
- 2016-01-13 ES ES16736999T patent/ES2907708T3/es active Active
- 2016-01-13 EP EP24184079.2A patent/EP4446301A3/en not_active Withdrawn
- 2016-01-13 AU AU2016206412A patent/AU2016206412B2/en not_active Ceased
- 2016-01-13 NZ NZ733343A patent/NZ733343A/en unknown
- 2016-01-13 CA CA2973036A patent/CA2973036C/en active Active
- 2016-01-13 FI FIEP21212648.6T patent/FI3988541T3/fi active
- 2016-01-13 WO PCT/CA2016/000008 patent/WO2016112455A1/en not_active Ceased
- 2016-01-13 JP JP2017536829A patent/JP6884100B2/ja active Active
- 2016-01-13 US US15/543,389 patent/US10654811B2/en active Active
- 2016-01-13 DK DK21212648.6T patent/DK3988541T3/da active
- 2016-01-13 ES ES21212648T patent/ES2987829T3/es active Active
- 2016-01-13 EP EP16736999.0A patent/EP3245193B1/en active Active
- 2016-01-13 EP EP21212648.6A patent/EP3988541B1/en active Active
- 2016-01-13 PT PT212126486T patent/PT3988541T/pt unknown
- 2016-01-13 DK DK16736999.0T patent/DK3245193T3/da active
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2017
- 2017-07-10 IL IL253394A patent/IL253394B/en active IP Right Grant
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2020
- 2020-05-01 US US16/864,479 patent/US11345670B2/en active Active
- 2020-09-14 AU AU2020233630A patent/AU2020233630B2/en not_active Ceased
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2021
- 2021-01-25 JP JP2021009453A patent/JP2021073248A/ja not_active Withdrawn
- 2021-02-16 IL IL280899A patent/IL280899B/en unknown
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2022
- 2022-04-26 US US17/729,780 patent/US20220267283A1/en not_active Abandoned
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2024
- 2024-08-01 US US18/791,751 patent/US20240391883A1/en active Pending
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