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US 10,618,933 B2Granted
Hydroxysteroid compounds, their intermediates, process of preparation, composition and uses thereof
AssigneeEpirium Bio Inc.
InventorsSundeep Dugar, Dinesh Mahajan, George Frederic Schreiner
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Abstract
The present invention relates to novel steroidal compounds of formula (I), process for preparation of the same and composition comprising these compounds.
Claims14
A hydroxysteroid compound having formula (I):
- or a salt thereof, wherein
- is independently either a single bond, a double bond or a cyclopropyl ring, provided that adjacent double bonds are not allowed;
- A1, A2, and A3 are independently selected from the group consisting of hydrogen, hydroxyl, halogen, and C1-C6 alkyl;
- B and C are each independently selected from the group consisting of hydrogen, hydroxyl, halogen, —OR6, —COR6, —COOR6, —OCOR6, —CH2OH, —CH2OR6, —CONHR6, —CONR6R7, —C(OH)R6R7, —NHR6, —NR6R7, C1-C12 straight or branched chain alkyl, and 5-6 membered heterocycloalkyl;
- wherein the C1-C12 straight or branched chain alkyl or 5-6 membered heterocycloalkyl is further optionally substituted with one or more substituents selected from the group consisting of halogen, C1-C6 alkyl, —OR6, —COOR6, —CONHR6, —OCOR6, ═NOH, —NR6R7, —NR6COR7, 5-6 membered heterocycloalkyl, and C1-C12 alkyl substituted 5-6 membered heterocycloalkyl;
- or B and C combine together to form ═O or ═NOR6;
- or B and C combine together with the carbon atom to which they are attached to form a 5-6 membered heterocycloalkyl, wherein said 5-6 membered heterocycloalkyl comprises one or more heteroatoms selected from the group consisting of O and N;
- R1 is selected from the group consisting of hydroxyl, ═O, —OR6, and -Otert-butyldimethylsilyl;
- R2 and R4 are independently selected from the group consisting of hydrogen, deuterium, and C1-C3 straight or branched chain alkyl;
- R3 is hydroxyl;
- wherein R3 is in a beta configuration;
- R5 is hydrogen;
- R6 and R7 are each independently selected from the group consisting of hydrogen, C1-C12 alkyl, —NH2, —(CH2)nNH2, 3-6 membered cycloalkyl, and 4-6 membered heterocycloalkyl;
- X is selected from the group consisting of NH and NR6;
- and
- n is 0 to 3;
- wherein when R1 is ═O, then B and C are not —CONHR6 or —CONR6R7.
14 more elements
A hydroxysteroid compound selected from the group consisting of:
- i. (4aR,5S,6aS)-5-hydroxy-4a,6a-dimethyl-4,4a,4b,5,6,6a,9,9a,9b,10-decahydro-1H-indeno[5,4-f]quinoline-2,7(3H,8H)-dione;
- ii. (4a′R,5'S,6a'S)-5′-hydroxy-4a′,5′,6a′-trimethyl-3′,4′,4a′,4b′,5′,6′,6a′,8′,9′,9a′,9b′,10′-dodecahydrospiro[[1,3]dioxolane-2,7′-indeno[5,4-f]quinolin]-2′(1′H)-one;
- iii. (4aR,5S,6aS)-4,4a,4b,5,6,6a,9,9a,9b,10-decahydro-5-hydroxy-4a,6a-dimethyl-1H-indeno[5,4-f]quinoline-2,7(3H,8H)-dione;
- iv. (4aR,5S,6aS)-7-acetyl-4,4a,4b,5,6,6a,7,8,9,9a,9b,10-dodecahydro-5-hydroxy-4a,5,6a-trimethyl-1H-indeno[5,4-f]quinolin-2(3H)-one;
- v. (4aR,6aS)-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-4a,6a-dimethyl-2,5-dioxo-1H-indeno[5,4-f]quinoline-7-carboxylic acid;
- vi. (4a′R,5'S,6a'S)-5′-hydroxy-4a′,6a′-dimethyl-3′,4′,4a′,4b′,5′,6′,6a′,8′,9′,9a′,9b′,10′-dodecahydrospiro[[1,3]dioxolane-2,7′-indeno[5,4-f]quinolin]-2′(1′H)-one;
- vii. (4aR,5R,6aS)-5-hydroxy-4a,5,6a-trimethyl-4,4a,4b,5,6,6a,9,9a,9b,10-decahydro-1H-indeno[5,4-f] quinoline-2,7(3H,8H)-dione;
- viii. (4aR,5S,6aS)-5,7-dihydroxy-4a,6a-dimethyl-4,4a,4b,5,6,6a,7,8,9,9a,9b,10-dodecahydro-1H-indeno[5,4-f]quinolin-2(3H)-one;
- ix. (4aR,5S,6aS)-7-fluoro-5-hydroxy-4a,6a-dimethyl-4,4a,4b,5,6,6a,7,8,9,9a,9b,10-dodecahydro-1H-indeno[5,4-f]quinolin-2(3H)-one;
- x. (4aR,5S,6aS,Z)-5-hydroxy-7-(hydroxyimino)-4a,6a-dimethyl-4,4a,4b,5,6,6a,7,8,9,9a,9b,10-dodecahydro-1H-indeno[5,4-f]quinolin-2(3H)-one;
- xi. (4aR,5S,6aS)-5,7-dihydroxy-1,4a,6a-trimethyl-4,4a,4b,5,6,6a,7,8,9,9a,9b,10-dodecahydro-1H-indeno[5,4-f]quinolin-2(3H)-one;
- xii. (4aR,5S,6aS)-5,7-dihydroxy-4a,6a-dimethyltetradecahydro-1H-indeno[5,4-f]quinolin-2(3H)-one;
- xiii. (4aR,5S,6aS)-7-amino-5-hydroxy-4a,6a-dimethyltetradecahydro-1H-indeno[5,4-f]quinolin-2(3H)-one;
- xiv. (4aR,5S,6aS,7S)-5-hydroxy-4a,6a-dimethyl-7-(2-methyl-1,3-dioxolan-2-yl)-4,4a,4b,5,6,6a,7,8,9,9a,9b,10-dodecahydro-1H-indeno[5,4-f]quinolin-2(3H)-one;
- xv. (4aR,5S,6aS,7S)-5-hydroxy-4a,5,6a-trimethyl-7-(2-methyl-1,3-dioxolan-2-yl)-4,4a,4b,5,6,6a,7,8,9,9a,9b,10-dodecahydro-1H-indeno[5,4-f]quinolin-2(3H)-one;
- xvi. (4aR,5S,6aS,7S)-5-hydroxy-4a,6a-dimethyl-2-oxo-2,3,4,4a,4b,5,6,6a,7,8,9,9a,9b,10-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid;
- xvii. (4aR,5S,6aS,7S)-7-acetyl-5-hydroxy-4a,6a-dimethyl-4,4a,4b,5,6,6a,7,8,9,9a,9b,10-dodecahydro-1H-indeno[5,4-f]quinolin-2(3H)-one;
- xviii. (4aR,5S,6aS,7S)-5-hydroxy-7-(2-hydroxypropan-2-yl)-4a,6a-dimethyl-4,4a,4b,5,6,6a,7,8,9a,9b,10-dodecahydro-1H-indeno[5,4-f]quinolin-2(3H)-one;
- xix. (4aR,5S,6aS,7S)-5-hydroxy-4a,6a-dimethyl-7-(2-methyl-1,3-dioxolan-2-yl)-4,4a,4b,5,6,6a,7,8,9,9a,9b,10-dodecahydro-1H-indeno[5,4-f]quinolin-2(3H)-one;
- and
- xx. (4aR,5S,6aS,7S)-5-hydroxy-4a,6a-dimethyl-2-oxo-2,3,4,4a,4b, 5,6,6a,7,8,9,9a,9b, 10-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxylic acid,
- or a pharmaceutically acceptable salt or stereoisomer each thereof.
19 more elements
Dependencies are inferred from the claim text.