Claims for Patent: 10,711,013

Summary for Patent: 10,711,013

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.
Inventor(s):	Gerd Wohlfahrt, Olli Törmäkangas, Harri Salo, Iisa Höglund, Arja Karjalainen, Pia Koivikko, Patrik Holm, Sirpa Rasku, Anniina Vesalainen
Assignee:	Orion Oyj
Application Number:	US16/140,716
Patent Claims:	1. A pharmaceutical dosage form comprising: a compound of formula (VI): wherein R1 is halogen; R2 is cyano; R3 is hydrogen, halogen, or methyl; R4 is hydrogen; R5 is methyl; ring A is any one of the following groups or tautomers thereof: R8 is hydrogen, C1-7 alkyl, or hydroxy C1-7 alkyl; and R9 is hydrogen, halogen, or C1-7 alkyl, or a pharmaceutically acceptable salt thereof; and a pharmaceutically acceptable excipient. 2. The dosage form according to claim 1, wherein ring A is or a tautomer thereof. 3. The dosage form according to claim 2, wherein R8 is hydroxy C1-7 alkyl; and R9 is hydrogen. 4. The dosage form according to claim 3, wherein R1 is chlorine; R3 is hydrogen; and R8 is 1-hydroxyethyl. 5. The dosage form according to claim 4, wherein the compound is N—((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)-propan-2-yl)-5-(1-hydroxyethyl)-1H-pyrazole-3-carboxamide. 6. The dosage form according to claim 4, wherein the compound is N—((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)-propan-2-yl)-3-(1-hydroxyethyl)-1H-pyrazole-5-carboxamide. 7. A compound of formula (VI): wherein R1 is halogen; R2 is cyano; R3 is hydrogen, halogen, or methyl; R4 is hydrogen; R5 is methyl; ring A is any one of the following groups or tautomers thereof: R8 is hydrogen, C1-7 alkyl, or hydroxy C1-7 alkyl; and R9 is hydrogen, halogen, or C1-7 alkyl, or a pharmaceutically acceptable salt thereof. 8. The compound according to claim 7, wherein ring A is or a tautomer thereof. 9. The compound according to claim 8, wherein R8 is hydroxy C1-7 alkyl; and R9 is hydrogen. 10. The compound according to claim 9, wherein R1 is chlorine; R3 is hydrogen; and R8 is 1-hydroxyethyl. 11. The compound according to claim 10, wherein the compound is N—((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)-propan-2-yl)-5-(1-hydroxyethyl)-1H-pyrazole-3-carboxamide. 12. The compound according to claim 10, wherein the compound is N—((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)-propan-2-yl)-3-(1-hydroxyethyl)-1H-pyrazole-5-carboxamide. 13. A mixture comprising (N—((S)-1-(3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-3-(1-hydroxyethyl)-1H-pyrazole-5-carboxamide and an isomer thereof. 14. A product produced by reducing (S)-3-acetyl-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-5-carboxamide. 15. The product of claim 14, wherein the reduction is the reaction of (S)-3-acetyl-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-5-carboxamide with ethanol and sodium borohydride. 16. A compound, which is (N—((S)-1-(3-(3-Chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-3-(1-hydroxyethyl)-1H-pyrazole-5-carboxamide or an isomer thereof. 17. A compound, which is N—((S)-1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)-propan-2-yl)-3-(1-hydroxyethyl)-1H-pyrazole-5-carboxamide or a tautomer thereof.