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Last Updated: April 5, 2025

Claims for Patent: 11,046,713

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Summary for Patent: 11,046,713

Title:	Androgen receptor modulating compounds
Abstract:	The present disclosure relates to compounds of formula (I), and pharmaceutically acceptable salts thereof. The present disclosure also relates to compositions and methods of treating comprising compounds of formula (I), and pharmaceutically acceptable salts thereof. ##STR00001##
Inventor(s):	Wohlfahrt; Gerd (Helsinki, FI), Tormakangas; Olli (Turku, FI), Salo; Harri (Turku, FI), Hoglund; Iisa (Turku, FI), Karjalainen; Arja (Espoo, FI), Koivikko; Pia (Littoinen, FI), Holm; Patrik (Lielahti, FI), Rasku; Sirpa (Vantaa, FI), Vesalainen; Anniina (Paimio, FI)
Assignee:	ORION CORPORATION (Espoo, FI)
Application Number:	16/799,270
Patent Claims:	1. A compound of formula (VI) ##STR00026## wherein R.sub.1 is halogen; R.sub.2 is cyano; R.sub.3 is hydrogen or halogen; R.sub.4 is hydrogen; R.sub.5 is methyl; ring A is any one of the following groups or tautomers thereof ##STR00027## R.sub.8 is C.sub.1-7 alkyl, hydroxy C.sub.1-7 alkyl or --C(O)R.sub.10; R.sub.9 is hydrogen; R.sub.10 is C.sub.1-7 alkyl; or a pharmaceutically acceptable salt thereof. 2. The compound according to claim 1, which is any one of the following compounds or tautomers thereof: (S)-3-acetyl-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl- )-1H-pyrazole-5-carboxamide; (R)-3-acetyl-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl- )-1H-pyrazole-5-carboxamide; N--((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)-propan-2-yl)-3-(1-- hydroxyethyl)-1H-pyrazole-5-carboxamide; (S)--N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(2-h- ydroxypropan-2-yl)isoxazole-3-carboxamide; (S)-5-acetyl-N-(1-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)propan-- 2-yl)-1H-pyrazole-3-carboxamide; (S)--N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-3-ethy- l-1,2,4-oxadiazole-5-carboxamide; (S)--N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-3-meth- yl-1,2,4-oxadiazole-5-carboxamide; (S)-5-acetyl-N-(1-(3-(4-cyano-3-iodophenyl)-1H-pyrazol-1-yl)propan-2-yl)-- 1H-pyrazole-3-carboxamide; N--((S)-1-(3-(4-cyano-3-iodophenyl)-1H-pyrazol-1-yl)propan-2-yl)-3-(1-hyd- roxyethyl)-1H-pyrazole-5-carboxamide; (S)--N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1-meth- yl-H-imidazole-4-carboxamide; (S)-3-acetyl-N-(1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)pr- opan-2-yl)-1H-pyrazole-5-carboxamide; (S)-5-acetyl-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl- )isoxazole-3-carboxamide; N--((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(1-h- ydroxyethyl)isoxazole-3-carboxamide; (S)-5-acetyl-N-(1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)pr- opan-2-yl)isoxazole-3-carboxamide; N--((S)-1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-y- l)-5-(1-hydroxyethyl)isoxazole-3-carboxamide; N--((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-2-(1-h- ydroxyethyl)oxazole-4-carboxamide; (S)--N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-isop- ropylisoxazole-3-carboxamide; N--((S)-1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-y- l)-3-(1-hydroxyethyl)-1H-pyrazole-5-carboxamide; (S)--N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(hyd- roxymethyl)isoxazole-3-carboxamide; (R)--N-(1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-y- l)-2-methyl-1H-imidazole-4-carboxamide; (S)-5-tert-butyl-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-- 2-yl)isoxazole-3-carboxamide; N--((R)-1-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-3-- (1-hydroxyethyl)-1H-pyrazole-5-carboxamide; (S)-3-acetyl-N-(1-(3-(3-chloro-4-cyano-2-fluorophenyl)-1H-pyrazol-1-yl)pr- opan-2-yl)-1H-pyrazole-5-carboxamide; (S)-3-acetyl-N-(1-(3-(3,5-dichloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-- 2-yl)-1H-pyrazole-5-carboxamide; N--((S)-1-(3-(3-chloro-4-cyano-2-fluorophenyl)-1H-pyrazol-1-yl)propan-2-y- l)-3-(1-hydroxyethyl)-1H-pyrazole-5-carboxamide; (S)--N-(1-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-3-- isopropyl-1,2,4-oxadiazole-5-carboxamide; N--((R)-1-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-- (1-hydroxyethyl)isoxazole-3-carboxamide; S)-5-acetyl-N-(1-(3-(3-chloro-4-cyano-2-fluorophenyl)-1H-pyrazol-1-yl)pro- pan-2-yl)isoxazole-3-carboxamide; N--((S)-1-(3-(3-chloro-4-cyano-2-fluorophenyl)-1H-pyrazol-1-yl)propan-2-y- l)-5-(1-hydroxyethyl)isoxazole-3-carboxamide; (S)--N-(1-(3-(3-chloro-4-cyano-2-fluorophenyl)-1H-pyrazol-1-yl)propan-2-y- l)-3-isopropyl-1,2,4-oxadiazole-5-carboxamide; N--((S)-1-(3-(3,5-dichloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-3-- (1-hydroxyethyl)-1H-pyrazole-5-carboxamide; S)--N-(1-(3-(3-chloro-4-cyano-2-fluorophenyl)-1H-pyrazol-1-yl)propan-2-yl- )-5-(2-hydroxypropan-2-yl)isoxazole-3-carboxamide; (S)--N-{1-[3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-2-meth- yl-1H-imidazole-4-carboxamide; (S)--N-{1-[3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl]propan-2-y- l}-2-methyl-1H-imidazole-4-carboxamide; (S)--N-{1-[3-(3-Chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl]propan-2-y- l}-1-methyl-1H-imidazole-4-carboxamide; (S)--N-{1-[3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1-ethy- l-1H-imidazole-4-carboxamide; (S)--N-{1-[3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1-(3-h- ydroxy-3-methylbutyl)-1H-imidazole-4-carboxamide; N--{(S)-1-[3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-1-(3-h- ydroxybutyl)-1H-imidazole-4-carboxamide; (S)--N-{1-[3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl]propan-2-yl}-3-isop- ropyl-1H-pyrazole-5-carboxamide; (S)--N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-3-isop- ropyl-1,2,4-oxadiazole-5-carboxamide; (S)--N-(1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-y- l)-2-(2-hydroxypropan-2-yl)oxazole-4-carboxamide; (S)--N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-2-(2-h- ydroxypropan-2-yl)oxazole-4-carboxamide; N--((S)-1-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-- (1-hydroxyethyl)-1H-pyrazole-3-carboxamide; (R)--N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-meth- ylisoxazole-3-carboxamide; N--((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(2-h- ydroxypropyl)isoxazole-3-carboxamide; (S)--N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-5-(2-h- ydroxyethyl)isoxazole-3-carboxamide; (S)--N-(1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)propan-2-y- l)-5-(2-hydroxypropan-2-yl)isoxazole-3-carboxamide; or a pharmaceutically acceptable salt thereof.

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