PT2176220E - Derivados de pirrolidin-2-ona como moduladores do receptor de androgénio - Google Patents

Info

Publication number

PT2176220E

PT2176220E PT87924304T PT08792430T PT2176220E PT 2176220 E PT2176220 E PT 2176220E PT 87924304 T PT87924304 T PT 87924304T PT 08792430 T PT08792430 T PT 08792430T PT 2176220 E PT2176220 E PT 2176220E

Authority

PT

Portugal

Prior art keywords

optionally

mixture

group

substituent

compound

Prior art date

2007-08-07

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• 239000000849 selective androgen receptor modulator Substances 0.000 title claims description 8
• HNJBEVLQSNELDL-YZRHJBSPSA-N pyrrolidin-2-one Chemical class O=C1CC[14CH2]N1 HNJBEVLQSNELDL-YZRHJBSPSA-N 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 295
• 125000001424 substituent group Chemical group 0.000 claims description 134
• -1 2-methylprop-2-enyl Chemical group 0.000 claims description 112
• 239000003795 chemical substances by application Substances 0.000 claims description 88
• 125000000217 alkyl group Chemical group 0.000 claims description 70
• 125000005843 halogen group Chemical group 0.000 claims description 69
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 56
• 150000003839 salts Chemical class 0.000 claims description 56
• 229910052799 carbon Inorganic materials 0.000 claims description 50
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 35
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 30
• 239000008177 pharmaceutical agent Substances 0.000 claims description 30
• 125000003342 alkenyl group Chemical group 0.000 claims description 23
• 238000011282 treatment Methods 0.000 claims description 21
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 210000003205 muscle Anatomy 0.000 claims description 19
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 15
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 150000001721 carbon Chemical group 0.000 claims description 15
• 238000011321 prophylaxis Methods 0.000 claims description 15
• 210000002307 prostate Anatomy 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 12
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• 125000003118 aryl group Chemical group 0.000 claims description 10
• 230000037396 body weight Effects 0.000 claims description 10
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
• 208000001132 Osteoporosis Diseases 0.000 claims description 8
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• 208000035475 disorder Diseases 0.000 claims description 8
• 206010058359 Hypogonadism Diseases 0.000 claims description 7
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• 239000003623 enhancer Substances 0.000 claims description 6
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
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• 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
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• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• DARLYICVLXBOGY-CPCISQLKSA-N 2-chloro-4-[(2s,3s)-3-hydroxy-2-methyl-5-oxopyrrolidin-1-yl]benzonitrile Chemical compound C[C@H]1[C@@H](O)CC(=O)N1C1=CC=C(C#N)C(Cl)=C1 DARLYICVLXBOGY-CPCISQLKSA-N 0.000 claims description 4
• SHAOFUWVZYWFRX-HJIKLVIJSA-N 2-chloro-4-[(2s,3s,4s)-2-ethyl-3-hydroxy-4-methyl-5-oxopyrrolidin-1-yl]benzonitrile Chemical compound CC[C@H]1[C@@H](O)[C@H](C)C(=O)N1C1=CC=C(C#N)C(Cl)=C1 SHAOFUWVZYWFRX-HJIKLVIJSA-N 0.000 claims description 4
• ROVSKDDUAFHOGB-WDEREUQCSA-N 2-chloro-4-[(4r,5s)-5-ethyl-3,3-difluoro-4-hydroxy-2-oxopyrrolidin-1-yl]benzonitrile Chemical compound CC[C@H]1[C@@H](O)C(F)(F)C(=O)N1C1=CC=C(C#N)C(Cl)=C1 ROVSKDDUAFHOGB-WDEREUQCSA-N 0.000 claims description 4
• LJQBTMVNFWIQQC-RYUDHWBXSA-N 4-[(2s,3s)-2-ethyl-3-hydroxy-5-oxopyrrolidin-1-yl]-2-(trifluoromethyl)benzonitrile Chemical compound CC[C@H]1[C@@H](O)CC(=O)N1C1=CC=C(C#N)C(C(F)(F)F)=C1 LJQBTMVNFWIQQC-RYUDHWBXSA-N 0.000 claims description 4
• SADHCJVAYWBWFE-CMPLNLGQSA-N 4-[(4r,5s)-5-ethyl-3,3-difluoro-4-hydroxy-2-oxopyrrolidin-1-yl]-2-methoxybenzonitrile Chemical compound CC[C@H]1[C@@H](O)C(F)(F)C(=O)N1C1=CC=C(C#N)C(OC)=C1 SADHCJVAYWBWFE-CMPLNLGQSA-N 0.000 claims description 4
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
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• 230000002829 reductive effect Effects 0.000 description 91
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• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 50
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