AU2005307003B2 - Novel heterocycle derivatives useful as selective androgen receptor modulators (SARMs) - Google Patents

Info

Publication number

AU2005307003B2

AU2005307003B2 AU2005307003A AU2005307003A AU2005307003B2 AU 2005307003 B2 AU2005307003 B2 AU 2005307003B2 AU 2005307003 A AU2005307003 A AU 2005307003A AU 2005307003 A AU2005307003 A AU 2005307003A AU 2005307003 B2 AU2005307003 B2 AU 2005307003B2

Authority

AU

Australia

Prior art keywords

alkyl

group

phenyl

methyl

hydrogen

Prior art date

2004-11-16

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.)

Ceased

Links

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• 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 10
• 239000000849 selective androgen receptor modulator Substances 0.000 title description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
• 102000001307 androgen receptors Human genes 0.000 claims abstract description 25
• 108010080146 androgen receptors Proteins 0.000 claims abstract description 25
• 208000035475 disorder Diseases 0.000 claims abstract description 25
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
• 150000001875 compounds Chemical class 0.000 claims description 520
• 125000000217 alkyl group Chemical group 0.000 claims description 458
• -1 cyano, nitro, amino Chemical group 0.000 claims description 365
• 238000000034 method Methods 0.000 claims description 215
• 229910052739 hydrogen Inorganic materials 0.000 claims description 214
• 239000001257 hydrogen Substances 0.000 claims description 213
• 150000002431 hydrogen Chemical class 0.000 claims description 130
• 229910052736 halogen Inorganic materials 0.000 claims description 85
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 83
• 229910052757 nitrogen Inorganic materials 0.000 claims description 82
• 150000002367 halogens Chemical class 0.000 claims description 75
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 71
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 70
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 62
• 239000002253 acid Substances 0.000 claims description 61
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 55
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 52
• 239000000203 mixture Substances 0.000 claims description 52
• 125000003545 alkoxy group Chemical group 0.000 claims description 51
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 48
• 125000001424 substituent group Chemical group 0.000 claims description 47
• 150000003839 salts Chemical class 0.000 claims description 40
• 125000003118 aryl group Chemical group 0.000 claims description 35
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 34
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 33
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 28
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 26
• 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 25
• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 25
• 125000001072 heteroaryl group Chemical group 0.000 claims description 25
• 229910052799 carbon Inorganic materials 0.000 claims description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
• 125000003282 alkyl amino group Chemical group 0.000 claims description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• PMDYLCUKSLBUHO-UHFFFAOYSA-N 4-amino-2-(trifluoromethyl)benzonitrile Chemical compound NC1=CC=C(C#N)C(C(F)(F)F)=C1 PMDYLCUKSLBUHO-UHFFFAOYSA-N 0.000 claims description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
• 230000001404 mediated effect Effects 0.000 claims description 18
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
• 125000004076 pyridyl group Chemical group 0.000 claims description 15
• 206010060862 Prostate cancer Diseases 0.000 claims description 14
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
• 208000030507 AIDS Diseases 0.000 claims description 13
• 208000002874 Acne Vulgaris Diseases 0.000 claims description 13
• 201000004384 Alopecia Diseases 0.000 claims description 13
• 208000000103 Anorexia Nervosa Diseases 0.000 claims description 13
• 206010006895 Cachexia Diseases 0.000 claims description 13
• 206010000496 acne Diseases 0.000 claims description 13
• 231100000360 alopecia Toxicity 0.000 claims description 13
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
• 239000003937 drug carrier Substances 0.000 claims description 13
• 201000001514 prostate carcinoma Diseases 0.000 claims description 13
• 206010006187 Breast cancer Diseases 0.000 claims description 12
• 208000026310 Breast neoplasm Diseases 0.000 claims description 12
• RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 11
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 10
• 125000003342 alkenyl group Chemical group 0.000 claims description 10
• 239000003098 androgen Substances 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 9
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 8
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 7
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 7
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
• ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 7
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
• 125000004432 carbon atom Chemical group C* 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
• RYBKPGYFXRNMMU-UHFFFAOYSA-N n-[4-cyano-3-(trifluoromethyl)phenyl]-5-methyl-3-(trifluoromethyl)-1,4-dihydropyrazole-5-carboxamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C1(C)CC(C(F)(F)F)=NN1 RYBKPGYFXRNMMU-UHFFFAOYSA-N 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 102000005962 receptors Human genes 0.000 claims description 6
• 108020003175 receptors Proteins 0.000 claims description 6
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
• 125000002346 iodo group Chemical group I* 0.000 claims description 5
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 125000001246 bromo group Chemical group Br* 0.000 claims description 4
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
• RYBKPGYFXRNMMU-GFCCVEGCSA-N (5r)-n-[4-cyano-3-(trifluoromethyl)phenyl]-5-methyl-3-(trifluoromethyl)-1,4-dihydropyrazole-5-carboxamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)[C@@]1(C)CC(C(F)(F)F)=NN1 RYBKPGYFXRNMMU-GFCCVEGCSA-N 0.000 claims description 3
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
• RYBKPGYFXRNMMU-LBPRGKRZSA-N (5s)-n-[4-cyano-3-(trifluoromethyl)phenyl]-5-methyl-3-(trifluoromethyl)-1,4-dihydropyrazole-5-carboxamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)[C@]1(C)CC(C(F)(F)F)=NN1 RYBKPGYFXRNMMU-LBPRGKRZSA-N 0.000 claims description 2
• PCJBAXPDQJKVPD-UHFFFAOYSA-N 3-(4-acetamidophenyl)-5-methyl-1,4-dihydropyrazole-5-carboxylic acid Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NNC(C)(C(O)=O)C1 PCJBAXPDQJKVPD-UHFFFAOYSA-N 0.000 claims description 2
• FPUAWRPFLJJPKB-UHFFFAOYSA-N 3-(4-acetamidophenyl)-5-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]-1,4-dihydropyrazole-5-carboxamide Chemical compound C1=CC(NC(=O)C)=CC=C1C1=NNC(C)(C(=O)NC=2C=C(C(=CC=2)[N+]([O-])=O)C(F)(F)F)C1 FPUAWRPFLJJPKB-UHFFFAOYSA-N 0.000 claims description 2
• FZVBSNLCPFQYET-UHFFFAOYSA-N 5-methyl-n-[4-nitro-3-(trifluoromethyl)phenyl]-3-[4-[(2,2,2-trifluoroacetyl)amino]phenyl]-1,4-dihydropyrazole-5-carboxamide Chemical compound N=1NC(C)(C(=O)NC=2C=C(C(=CC=2)[N+]([O-])=O)C(F)(F)F)CC=1C1=CC=C(NC(=O)C(F)(F)F)C=C1 FZVBSNLCPFQYET-UHFFFAOYSA-N 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• DLPFHGUGJWOGOG-UHFFFAOYSA-N n-[4-cyano-3-(trifluoromethyl)phenyl]-5-ethyl-3-(trifluoromethyl)-1,4-dihydropyrazole-5-carboxamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C1(CC)CC(C(F)(F)F)=NN1 DLPFHGUGJWOGOG-UHFFFAOYSA-N 0.000 claims description 2
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims 1
• 125000001207 fluorophenyl group Chemical group 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 185
• 238000005481 NMR spectroscopy Methods 0.000 description 179
• 239000007787 solid Substances 0.000 description 175
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 82
• 235000019439 ethyl acetate Nutrition 0.000 description 63
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
• 239000011541 reaction mixture Substances 0.000 description 44
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 37
• 239000000460 chlorine Substances 0.000 description 34
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
• 239000011734 sodium Substances 0.000 description 30
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
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• 239000012267 brine Substances 0.000 description 23
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