TW201835064A

TW201835064A - 苯并噻吩雌激素受體調節劑

苯并噻吩雌激素受體調節劑 Download PDF

Info

Publication number: TW201835064A
Authority: TW; Taiwan
Prior art keywords: compound; alkyl; formula; pharmaceutically acceptable; cancer
Prior art date: 2017-02-10

Application number

TW107104795A

Other languages

English (en)

Chinese (zh)

Inventor

傑 C 斯壯姆

Original Assignee

美商G1治療公司

Priority date

2017-02-10

Filing date

2018-02-09

Publication date

2018-10-01

2018-02-09 Application filed by 美商G1治療公司 filed Critical 美商G1治療公司

2018-10-01 Publication of TW201835064A publication Critical patent/TW201835064A/zh

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FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title abstract description 21
239000002834 estrogen receptor modulator Substances 0.000 title abstract 2
150000003839 salts Chemical class 0.000 claims abstract description 107
229940011871 estrogen Drugs 0.000 claims abstract description 40
239000000262 estrogen Substances 0.000 claims abstract description 40
150000001875 compounds Chemical class 0.000 claims description 344
206010028980 Neoplasm Diseases 0.000 claims description 97
125000000217 alkyl group Chemical group 0.000 claims description 97
201000011510 cancer Diseases 0.000 claims description 54
125000001188 haloalkyl group Chemical group 0.000 claims description 52
125000000623 heterocyclic group Chemical group 0.000 claims description 52
238000011282 treatment Methods 0.000 claims description 48
239000003814 drug Substances 0.000 claims description 40
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
208000026310 Breast neoplasm Diseases 0.000 claims description 31
238000004519 manufacturing process Methods 0.000 claims description 31
206010006187 Breast cancer Diseases 0.000 claims description 30
229910052736 halogen Inorganic materials 0.000 claims description 27
150000002367 halogens Chemical class 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
239000003937 drug carrier Substances 0.000 claims description 20
206010033128 Ovarian cancer Diseases 0.000 claims description 19
206010061535 Ovarian neoplasm Diseases 0.000 claims description 19
239000008194 pharmaceutical composition Substances 0.000 claims description 18
150000002431 hydrogen Chemical class 0.000 claims description 17
125000002619 bicyclic group Chemical group 0.000 claims description 15
229940079593 drug Drugs 0.000 claims description 14
206010014733 Endometrial cancer Diseases 0.000 claims description 9
206010014759 Endometrial neoplasm Diseases 0.000 claims description 9
229910052805 deuterium Inorganic materials 0.000 claims description 9
125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 8
125000002950 monocyclic group Chemical group 0.000 claims description 8
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 5
150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 4
229940124597 therapeutic agent Drugs 0.000 claims description 4
239000000203 mixture Substances 0.000 abstract description 66
-1 tetrahydropyrido [3,4-b] indole-1-yl compounds Chemical class 0.000 description 134
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238000000034 method Methods 0.000 description 76
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238000000746 purification Methods 0.000 description 33
238000005160 1H NMR spectroscopy Methods 0.000 description 32
230000000694 effects Effects 0.000 description 32
239000003112 inhibitor Substances 0.000 description 32
230000000670 limiting effect Effects 0.000 description 32
210000004027 cell Anatomy 0.000 description 30
125000003118 aryl group Chemical group 0.000 description 28
125000000753 cycloalkyl group Chemical group 0.000 description 28
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 27
FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 description 25
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 18
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 17
239000002552 dosage form Substances 0.000 description 17
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125000003710 aryl alkyl group Chemical group 0.000 description 13
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LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 13
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125000004432 carbon atom Chemical group C* 0.000 description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
238000004128 high performance liquid chromatography Methods 0.000 description 11
201000010982 kidney cancer Diseases 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 10
206010065687 Bone loss Diseases 0.000 description 10
206010055113 Breast cancer metastatic Diseases 0.000 description 10
125000001246 bromo group Chemical group Br* 0.000 description 10
230000015556 catabolic process Effects 0.000 description 10
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238000006731 degradation reaction Methods 0.000 description 10
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229910052757 nitrogen Inorganic materials 0.000 description 10
230000000269 nucleophilic effect Effects 0.000 description 10
229910052760 oxygen Inorganic materials 0.000 description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
239000002904 solvent Substances 0.000 description 10
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
229910015845 BBr3 Inorganic materials 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
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238000003556 assay Methods 0.000 description 9
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WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 8
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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