C17, c20, and c21 substituted neuroactive steroids and their methods of use

A compound of Formula (2-A),

• or a pharmaceutically acceptable salt thereof, wherein
• R3 is —CH3, —CF3, —CH2OOCH3, —CH2OCH2CH3;
• R19 is hydrogen, —CH3, or —CH2ORA1, wherein RA1 is optionally substituted alkyl;
• R3 is —CH3, —CF3, —CH2OCH3, —CH2OCH2CH3;
• R17a is —NRA2RA3, —N(R1)C(O)RA2, —N(R1)SO2RA2, —ORA3, cycloalkyl, heterocyclyl, aryl, or heteroaryl, wherein each of RA2 and RA3 is independently hydrogen, carbocyclyl, heterocyclyl, aryl, heteroaryl, or —ORA4, wherein RA4 is hydrogen or alkyl;
• or R17A is
• wherein A is oxazolyl or thiazolyl;
• R17b is hydrogen, hydroxyl, alkyl, or alkoxy;
• and
• represents a single or double bond, wherein when one is a double bond, the other is a single bond and R5 is absent;
• provided that:
• i. when R17a is oxazolyl, or
• then R17b is not hydrogen, or
• ii. when R17a is heterocyclyl, then R19 is hydrogen, or
• ii. when R17a is —ORA4, then R19 is hydrogen.

A compound of Formula (3-A)

• or a pharmaceutically acceptable salt thereof, wherein
• R19 is hydrogen or alkyl;
• R17a is nitro or alkoxy;
• each of R2, R4, R11a, or R11b is independently hydrogen, alkyl, or alkoxy, or R11a and R11b are joined together to form oxo;
• represents a single or double bond, wherein when one is a double bond, the other is a single bond and R5 is absent;
• and
• R5 is absent or hydrogen as determined by valency;
• provided that,
• i. when R2, R11a, and R11b are hydrogen, then R4 is alkyl, or
• ii. when R4, R11a, and R11b are hydrogen, then R2 is alkyl, or
• iii. when R4 is hydrogen, then R2 is —OH or alkoxy, R11a is hydrogen, and R11b is —OH or alkoxy, or R2 is —OH or alkoxy and R11a and R11b are joined together to form oxo.