The invention relates to a process for the preparation of 11-methylene steroids through selective olefination of the ketone at position 11. The resulting products are useful intermediates in the preparation of several pharmaceutically active agents, such as Etonogestrel and Desogestrel.

Described herein are neuroactive steroids of the Formula (I): or a pharmaceutically acceptable salt thereof; wherein -----, R.sup.1, R.sup.2, R.sup.5, A and L are as defined herein. Such compounds are envisioned, in certain embodiments, to behave as GABA modulators. The present invention also provides pharmaceutical compositions comprising a compound of the present invention and methods of use and treatment, e.g., such for inducing sedation and/or anesthesia.

##STR00001##

Provided herein is a compound of Formula (I), or a pharmaceutically acceptable salt thereof, wherein R.sup.2a, R.sup.2b, R.sup.3, R.sup.4a, R.sup.4b, R.sup.5, R.sup.6a, R.sup.6b, R.sup.11a, R.sup.11b, R.sup.15a, R.sup.15b, R.sup.16a, R.sup.16b, R.sup.18, R.sup.19, R.sup.20a, R.sup.20b, X, A, Z, q, u, r, s, t, m, and n are defined herein. Also provided herein are pharmaceutical compositions comprising a compound of Formula (I) and methods of using the compounds, e.g., in the treatment of CNS-related disorders.

##STR00001##

Disclosed are compounds of the formula: ##STR00001##
wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently hydrogen, C.sub.1-C.sub.6 alkyl, halo, a sulfate, a glucuronide, OH, a bulky group, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, N(CH.sub.2).sub.n; a phosphate group, and a phosphinate group; R.sub.9 is hydrogen, halogen or alkyl; R.sub.11 is selected from the group consisting of H, C.sub.1-C.sub.6 alkyl, halogen, a sulfate, a glucoronide, SO.sub.2NH.sub.2, COOH, CN, CH.sub.2CN, NHCN, CHO, CHOCH.sub.3, COO salt, OSO.sub.2alkyl, NH.sub.2, and NHCO(CH.sub.2).sub.n; R.sub.12 is selected from the group consisting of H, a C.sub.1-C.sub.6 alkyl, a sulfate, a glucoronide, a bulky group, aryl, cycloalkyl, heteroaryl and heterocycloalkyl; X is selected from the group consisting of C.sub.1-C.sub.12 alkyl, C.sub.2-C.sub.12 alkenyl, C.sub.2-C.sub.12 alkynyl, halogen, a glucoronide, NH.sub.2, SO.sub.2NH.sub.2, COOH, CN, CH.sub.2CN, NHCN, CHO, COOsalt, OSO.sub.2alkyl, SH, SCH.sub.3, CH[(CH.sub.2).sub.nCH.sub.3]COOCH.sub.3, (CH.sub.2).sub.mCOOCH.sub.3, (CH.sub.2).sub.mOCH.sub.3, (CH.sub.2).sub.mO(CH.sub.2).sub.nCH.sub.3, (CH.sub.2).sub.mSCH.sub.3, (CH.sub.2).sub.mS(CH.sub.2).sub.nCH.sub.3, (CH.sub.2).sub.mNH(CH.sub.2).sub.nCH.sub.3, C.sub.2-C.sub.8 alkenyl-O(CH.sub.2).sub.nCH.sub.3, C.sub.2-C.sub.8 alkenyl-S(CH.sub.2).sub.nCH.sub.3, C.sub.2-C.sub.8 alkenyl-N(CH.sub.2).sub.nCH.sub.3, C.sub.2-C.sub.8 alkynyl-O(CH.sub.2).sub.nCH.sub.3, C.sub.2-C.sub.8 alkynyl-S(CH.sub.2).sub.nCH.sub.3, C.sub.2-C.sub.8 alkynyl-N(CH.sub.2).sub.nCH.sub.3, (CH.sub.2).sub.mOH, (CH.sub.2).sub.mONH.sub.2, (CH.sub.2).sub.mSNH.sub.2, NH(CH.sub.2).sub.mCH.sub.3, NH(CH.sub.2).sub.mOCH.sub.3, NH(CH.sub.2).sub.mCHOHCOOH, N(CH.sub.3).sub.2, (CH.sub.2).sub.m(NH)CH.sub.2OH, NHCOOH, (CH.sub.2).sub.mNHCOOH, NO.sub.2, SCN, SO.sub.2alkyl, B(OH).sub.2, (CH.sub.2).sub.mN(CH.sub.3)SO.sub.2NH.sub.3, (CH.sub.2).sub.mNHSO.sub.2NH.sub.2, NHC(S) CH.sub.3, and NHNH.sub.2; and Y is selected from hydrogen, O, OCO(R.sub.6) and OH; wherein m is an integer between 0-20, n is an integer between 0-8, the symbol represents either a single or a double bond capable of forming a keto group at position 3 or 17; and the symbol represents any type of bond regardless of the stereochemistry; and the respective enantiomers, othe

Described herein are neuroactive steroids of the Formula (I): or a pharmaceutically acceptable salt thereof; wherein -------, R.sup.1, R.sup.2, R.sup.3, A and L are as defined herein. Such compounds are envisioned, in certain embodiments, to behave as GABA modulators. The present invention also provides pharmaceutical compositions comprising a compound of the present invention and methods of use and treatment, e.g., such for inducing sedation and/or anesthesia. ##STR00001##

The present disclosure relates to stereodefined polycyclic (e.g., tetracyclic) compounds that contain quaternary centers at one or multiple ring fusions, synthetic methods for preparing such compounds, and methods of using such compounds to treat a disease, such as a brain tumor and, particularly, a glioma.

Provided herein is a compound of Formula (I) ##STR00001##
or a pharmaceutically acceptable salt thereof, wherein R.sup.3a, R.sup.5, R.sup.6a, R.sup.6b, R.sup.17, R.sup.21a, R.sup.21b, R.sup.m, R.sup.n, R.sup.16a, R.sup.16b, R.sup.7a, R.sup.7b, R.sup.12a, R.sup.12b, R.sup.11a, R.sup.11b, R.sup.2a, R.sup.2b, R.sup.19, R.sup.4a, and R.sup.4b are defined herein. Also provided herein are pharmaceutical compositions comprising a compound of Formula (I) and methods of using the compounds, e.g., in the treatment of CNS-related disorders.

Provided herein are 19-nor C3,3-disubstituted C21-pyrazolyl steroids of Formula (I):

##STR00001##

and pharmaceutically acceptable salts thereof; wherein , R.sup.1, R.sup.2, R.sup.3a, R.sup.3b, R.sup.4a, R.sup.4b, R.sup.5, R.sup.6, and R.sup.7 are as defined herein. Such compounds are contemplated useful for the prevention and treatment of a variety of CNS-related conditions, for example, treatment of sleep disorders, mood disorders, schizophrenia spectrum disorders, convulsive disorders, disorders of memory and/or cognition, movement disorders, personality disorders, autism spectrum disorders, pain, traumatic brain injury, vascular diseases, substance abuse disorders and/or withdrawal syndromes, and tinnitus.

Provided herein in part is a compound of Formula (I): or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising a compound of Formula I, and methods of using the compounds, e.g, in the treatment of CNS-related disorders.

##STR00001##

A process is provided for the making of estetrol starting from a 3-A-oxy-estra-1,3,5(10),15-tetraen-17-one, wherein A is an C.sub.1-C.sub.5 alkyl group, preferably a methyl group, or a C.sub.7-C.sub.12 benzylic group, preferably a benzyl group. This process is particularly suitable to industry.