CA2620275A1

CA2620275A1 - Non-steroidal antiandrogens

Non-steroidal antiandrogens Download PDF

Info

Publication number: CA2620275A1
Authority: CA; Canada
Prior art keywords: substituted; alkyl; aryl; heteroarylalkyl; carbamoyl
Prior art date: 2005-08-26
Legal status : Abandoned

Application number

CA002620275A

Other languages

English (en)

French (fr)

Inventor

Thomas S. Scanlan

Dmitry V. Kadnikov

Current Assignee

University of California San Diego UCSD

Original Assignee

Individual

Priority date

2005-08-26

Filing date

2006-08-28

Publication date

2007-03-01

2006-08-28 Application filed by Individual filed Critical Individual

2007-03-01 Publication of CA2620275A1 publication Critical patent/CA2620275A1/en

Status Abandoned legal-status Critical Current

Links

239000003956 nonsteroidal anti androgen Substances 0.000 title description 3
239000000203 mixture Substances 0.000 claims abstract description 90
108010080146 androgen receptors Proteins 0.000 claims abstract description 66
238000000034 method Methods 0.000 claims abstract description 42
206010060862 Prostate cancer Diseases 0.000 claims abstract description 27
208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 26
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 261
125000003710 aryl alkyl group Chemical group 0.000 claims description 255
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 232
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 229
125000004404 heteroalkyl group Chemical group 0.000 claims description 223
125000003282 alkyl amino group Chemical group 0.000 claims description 214
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 205
125000004414 alkyl thio group Chemical group 0.000 claims description 205
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 204
125000004663 dialkyl amino group Chemical group 0.000 claims description 204
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 203
125000001072 heteroaryl group Chemical group 0.000 claims description 196
125000002252 acyl group Chemical group 0.000 claims description 194
125000004442 acylamino group Chemical group 0.000 claims description 193
150000001875 compounds Chemical class 0.000 claims description 184
239000001257 hydrogen Substances 0.000 claims description 180
229910052739 hydrogen Inorganic materials 0.000 claims description 180
125000000217 alkyl group Chemical group 0.000 claims description 178
150000002431 hydrogen Chemical class 0.000 claims description 162
125000003118 aryl group Chemical group 0.000 claims description 158
-1 carboxy, cyano, nitro, chloro, bromo, iodo, thio Chemical group 0.000 claims description 151
125000000547 substituted alkyl group Chemical group 0.000 claims description 145
125000003107 substituted aryl group Chemical group 0.000 claims description 142
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 122
229910052799 carbon Inorganic materials 0.000 claims description 120
150000001721 carbon Chemical group 0.000 claims description 119
125000004093 cyano group Chemical group *C#N 0.000 claims description 118
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 116
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125000003545 alkoxy group Chemical group 0.000 claims description 91
125000005415 substituted alkoxy group Chemical group 0.000 claims description 90
125000004432 carbon atom Chemical group C* 0.000 claims description 83
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 68
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125000005010 perfluoroalkyl group Chemical group 0.000 claims description 27
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
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239000001301 oxygen Chemical group 0.000 claims description 21
230000000694 effects Effects 0.000 claims description 20
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IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
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QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
230000004913 activation Effects 0.000 claims description 5
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230000008484 agonism Effects 0.000 claims description 4
125000001475 halogen functional group Chemical group 0.000 claims 34
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CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 2
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MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical compound [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 claims 1
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125000004122 cyclic group Chemical group 0.000 description 9
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235000017557 sodium bicarbonate Nutrition 0.000 description 7
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238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
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