US 11,325,940 B2Granted

Certain chemical entities, compositions, and methods

AssigneeNeupharma, Inc.

InventorXiangping Qian

Life of this patent

Estimating the term…

Abstract

Chemical entities that are novel compounds, pharmaceutical compositions and methods of treatment of cancer are described.

Claims20

Dependent claims

A compound selected from the group consisting of:

N-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)morpholine-4-carboxamide;
N-((3R,5R,8R,9 S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)piperazine-1-carboxamide;
N-((3S,5R,8R,9S,10 S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)piperazine-1-carboxamide;
N-((3S,5R,8R,9S,10 S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)pyrrolidine-1-carboxamide;
1-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-3-(2-hydroxyethyl)urea;
1-(2-aminoethyl)-3-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)urea;
2-amino-N-((3R,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)acetamide;
2-amino-N-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)acetamide;
(S)—N-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)pyrrolidine-2-carboxamide;
5-((5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-(piperazin-1-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2H-pyran-2-one;
N-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)methanesulfonamide;
methyl ((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)carbamate;
methyl ((5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)(methyl)carbamate;
(R)-2-amino-N-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-3-methylbutanamide;
(R)-2-amino-N-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)propanamide;
N-((5 S,8R,9S,10R,13R,14S,17R)-5,14-dihydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)morpholine-4-carboxamide;
and
(2R)—N-((5 S,8R,9S,10R,13R,14S,17R)-5,14-dihydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)pyrrolidine-2-carboxamide;
or a pharmaceutically acceptable salt thereof.

16 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/595,749Filed 8 Oct 2019 · continuation
Priority: 29 Apr 2012
Published: US 2020/0102344 A12 Apr 2020
Granted: 10 May 2022
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07J 41/0011
The nitrogen atom being directly linked to the cyclopentahydro phenanthrene skeleton: unsubstituted amino radicals
A61P 35/00
Antineoplastic agents
C07J 19/00
Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17
C07J 41/0005
Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring: the nitrogen atom being directly linked to the…

Family

Application61/639,930Us provisional application · filed 29 Apr 2012
PCT/US2013/038705Parent of this continuation · filed 29 Apr 2013
Application15/586,710Parent of this continuation · filed 4 May 2017
US 9,676,813 B2Parent of this continuation · filed 13 Jun 2017
US 2020/0102344 A1Pre-grant publication · published 2 Apr 2020
US 10,487,108 B2Parent of this continuation
Application14/397,845Parent of this continuation
US 2016/0039865 A1Published application
US 2017/0362271 A1Published application
US 11,325,940 B2This patent

From the US filing history. Foreign family members aren’t listed.

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A compound selected from the group consisting of:

N-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)morpholine-4-carboxamide;
N-((3R,5R,8R,9 S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)piperazine-1-carboxamide;
N-((3S,5R,8R,9S,10 S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)piperazine-1-carboxamide;
N-((3S,5R,8R,9S,10 S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)pyrrolidine-1-carboxamide;
1-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-3-(2-hydroxyethyl)urea;
1-(2-aminoethyl)-3-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)urea;
2-amino-N-((3R,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)acetamide;
2-amino-N-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)acetamide;
(S)—N-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)pyrrolidine-2-carboxamide;
5-((5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-(piperazin-1-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2H-pyran-2-one;
N-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)methanesulfonamide;
methyl ((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)carbamate;
methyl ((5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)(methyl)carbamate;
(R)-2-amino-N-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)-3-methylbutanamide;
(R)-2-amino-N-((3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)propanamide;
N-((5 S,8R,9S,10R,13R,14S,17R)-5,14-dihydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)morpholine-4-carboxamide;
and
(2R)—N-((5 S,8R,9S,10R,13R,14S,17R)-5,14-dihydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl)pyrrolidine-2-carboxamide;
or a pharmaceutically acceptable salt thereof.

16 more elements

Facts

Application

16/595,749Filed 8 Oct 2019 · continuation

Priority

29 Apr 2012

Published

US 2020/0102344 A12 Apr 2020

Granted

10 May 2022

Term ends

Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07J 41/0011
The nitrogen atom being directly linked to the cyclopentahydro phenanthrene skeleton: unsubstituted amino radicals
A61P 35/00
Antineoplastic agents
C07J 19/00
Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17
C07J 41/0005
Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring: the nitrogen atom being directly linked to the…

Family

Application61/639,930Us provisional application · filed 29 Apr 2012

PCT/US2013/038705Parent of this continuation · filed 29 Apr 2013

Application15/586,710Parent of this continuation · filed 4 May 2017

US 9,676,813 B2Parent of this continuation · filed 13 Jun 2017

US 2020/0102344 A1Pre-grant publication · published 2 Apr 2020

US 10,487,108 B2Parent of this continuation

Application14/397,845Parent of this continuation

US 2016/0039865 A1Published application

US 2017/0362271 A1Published application

US 11,325,940 B2This patent

From the US filing history. Foreign family members aren’t listed.