US 2016/0257707 A1Published application

Taccalonolide microtubule stabilizers

AssigneeBoard of Regents, The University of Texas System

InventorsSusan L. MOOBERRY, Jiangnan PENG, April L. RISINGER, Jing LI

Life of this patent

Estimating the term…

Abstract

The invention provides epoxytaccalonolide microtubule stabilizers and their use as anti-proliferative microtubule stabilizing agents.

Claims20

Dependent claims

A compound of the formula:

wherein:
R1 is hydrogen, amino, cyano, azido, halo, hydroxy, oxo, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R2 is hydrogen, amino, cyano, azido, halo, hydroxy, oxo, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof, or R2 is taken together with R3 to form an epoxide at C-2/C-3;
R3 is hydrogen, amino, cyano, azido, halo, hydroxy, oxo, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), and substituted versions thereof, or R3 is taken together with R2 as defined above;
R5 is absent, hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R6 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof, or oxo if R6′ is not present, or R6 is taken together with R7 to form an epoxide at C-6/C-7;
R6′ when present is hydrogen, amino, cyano, azido, halo, hydroxy, alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R7 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof, or oxo if R7′ is not present, or R7 is taken together with R6 as defined above;
R7′ when present is hydrogen, amino, cyano, azido, halo, hydroxy, alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R11 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R12 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R15 is hydrogen, amino, cyano, azido, halo, hydroxy, oxo, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R20 is hydrogen, amino, cyano, azido, halo, hydroxy, hydroperoxy, alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof,
R21 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof,
R25 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof,
R26 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof, or oxo if R26′ is not present;
R26′ when present is hydrogen, amino, cyano, azido, halo, hydroxy, alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R27 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
and
X is O, NR′ or CR′2, wherein each R′ is independently hydrogen or alkyl(C≦6);
or a pharmaceutically acceptable salt thereof,
wherein the —O— bridging C-22 and C-23 is optionally replaced with a double bond between C-22 and C-23;
provided, however, that Formula I does not include the compound wherein R1 is acetoxy, R2 taken together with R3 forms an epoxide at C-2/C-3;
R5 is hydrogen, R6 is oxo and R6′ is not present, R7 is hydroxy and R7′ is hydrogen, each of R11, R12 and R15 are acetoxy, one of R20 or R21 is methyl and the other is hydrogen, R25 is OH, R26 is oxo and R26′ is not present, R27 is methyl, and X is O.

21 more elements

A composition comprising at least 90% by weight of a compound of Formula I, wherein Formula I has the structure:

wherein:
R1 is hydrogen, amino, cyano, azido, halo, hydroxy, oxo, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R2 is hydrogen, amino, cyano, azido, halo, hydroxy, oxo, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof, or R2 is taken together with R3 to form an epoxide at C-2/C-3;
R3 is hydrogen, amino, cyano, azido, halo, hydroxy, oxo, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), and substituted versions thereof, or R3 is taken together with R2 as defined above;
R5 is absent, hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R6 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof, or oxo if R6′ is not present, or R6 is taken together with R7 to form an epoxide at C-6/C-7;
R6′ when present is hydrogen, amino, cyano, azido, halo, hydroxy, alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R7 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof, or oxo if R7′ is not present, or R7 is taken together with R6 as defined above;
R7′ when present is hydrogen, amino, cyano, azido, halo, hydroxy, alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R11 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R12 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R15 is hydrogen, amino, cyano, azido, halo, hydroxy, oxo, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof,
R20 is hydrogen, amino, cyano, azido, halo, hydroxy, hydroperoxy, alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof,
R21 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof,
R25 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof,
R26 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof, or oxo if R26′ is not present;
R26′ when present is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R27 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
and
X is O, NR′ or CR′2, wherein each R′ is independently hydrogen or alkyl(C≦6);
or a pharmaceutically acceptable salt thereof,
wherein the —O— bridging C-22 and C-23 is optionally replaced with a double bond between C-22 and C-23.

19 more elements

A composition comprising a compound of Formula I and a pharmaceutically acceptable carrier therefor, wherein Formula I has the structure:

wherein:
R1 is hydrogen, amino, cyano, azido, halo, hydroxy, oxo, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R2 is hydrogen, amino, cyano, azido, halo, hydroxy, oxo, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof, or R2 is taken together with R3 to form an epoxide at C-2/C-3;
R3 is hydrogen, amino, cyano, azido, halo, hydroxy, oxo, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), and substituted versions thereof, or R3 is taken together with R2 as defined above;
R5 is absent, hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R6 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof, or oxo if R6′ is not present, or R6 is taken together with R7 to form an epoxide at C-6/C-7;
R6′ when present is hydrogen, amino, cyano, azido, halo, hydroxy, alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R7 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof, or oxo if R7′ is not present, or R7 is taken together with R6 as defined above;
R7′ when present is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R11 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof,
R12 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof,
R15 is hydrogen, amino, cyano, azido, halo, hydroxy, oxo, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof,
R20 is hydrogen, amino, cyano, azido, halo, hydroxy, hydroperoxy, alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof,
R21 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof,
R25 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof,
R26 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof, or oxo if R26′ is not present;
R26′ when present is hydrogen, amino, cyano, azido, halo, hydroxy, alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R27 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
and
X is O, NR′ or CR′2, wherein each R′ is independently hydrogen or alkyl(C≦6);
or a pharmaceutically acceptable salt thereof,
wherein the —O— bridging C-22 and C-23 is optionally replaced with a double bond between C-22 and C-23.

19 more elements

Dependencies are inferred from the claim text.

Facts

Application: 15/153,470Filed 12 May 2016
Priority: 6 Jun 2011
Published: 8 Sep 2016
Term ends: Not estimatedThe source records don’t support an estimate.

Classification10 codes

C07J 71/001
Oxygen-containing hetero ring: oxiranes
A61K 31/585
Containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin: containing lactone rings, e.g. oxandrolone, bufalin
A61K 36/894
Liliopsida: dioscoreaceae
A61P 35/00
Antineoplastic agents

Family

Application61/493,653Us provisional application · filed 6 Jun 2011
Application61/535,202Us provisional application · filed 15 Sep 2011
Application14/096,876Continuation · filed 4 Dec 2013
Application15/153,470Continuation
US 2014/0357608 A1Published application
US 9,340,572 B2Related patent
US 2016/0257707 A1This patent

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

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A compound of the formula:

wherein:
R1 is hydrogen, amino, cyano, azido, halo, hydroxy, oxo, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R2 is hydrogen, amino, cyano, azido, halo, hydroxy, oxo, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof, or R2 is taken together with R3 to form an epoxide at C-2/C-3;
R3 is hydrogen, amino, cyano, azido, halo, hydroxy, oxo, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), and substituted versions thereof, or R3 is taken together with R2 as defined above;
R5 is absent, hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R6 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof, or oxo if R6′ is not present, or R6 is taken together with R7 to form an epoxide at C-6/C-7;
R6′ when present is hydrogen, amino, cyano, azido, halo, hydroxy, alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R7 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof, or oxo if R7′ is not present, or R7 is taken together with R6 as defined above;
R7′ when present is hydrogen, amino, cyano, azido, halo, hydroxy, alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R11 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R12 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R15 is hydrogen, amino, cyano, azido, halo, hydroxy, oxo, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R20 is hydrogen, amino, cyano, azido, halo, hydroxy, hydroperoxy, alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof,
R21 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof,
R25 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof,
R26 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof, or oxo if R26′ is not present;
R26′ when present is hydrogen, amino, cyano, azido, halo, hydroxy, alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
R27 is hydrogen, amino, cyano, azido, halo, hydroxy, alkyl(C≦12), alkenyl(C≦12), alkoxy(C≦12), acyl(C≦12), acyloxy(C≦12), alkylamino(C≦12), dialkylamino(C≦12), amido(C≦12), alkylthio(C≦12), aryl(C≦12), aralkyl(C≦12), heterocycloalkyl(C≦12), or substituted versions thereof;
and
X is O, NR′ or CR′2, wherein each R′ is independently hydrogen or alkyl(C≦6);
or a pharmaceutically acceptable salt thereof,
wherein the —O— bridging C-22 and C-23 is optionally replaced with a double bond between C-22 and C-23;
provided, however, that Formula I does not include the compound wherein R1 is acetoxy, R2 taken together with R3 forms an epoxide at C-2/C-3;
R5 is hydrogen, R6 is oxo and R6′ is not present, R7 is hydroxy and R7′ is hydrogen, each of R11, R12 and R15 are acetoxy, one of R20 or R21 is methyl and the other is hydrogen, R25 is OH, R26 is oxo and R26′ is not present, R27 is methyl, and X is O.

21 more elements

Facts

Application

15/153,470Filed 12 May 2016

Priority

6 Jun 2011

Published

8 Sep 2016

Term ends

Not estimatedThe source records don’t support an estimate.

Classification10 codes

C07J 71/001
Oxygen-containing hetero ring: oxiranes
A61K 31/585
Containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin: containing lactone rings, e.g. oxandrolone, bufalin
A61K 36/894
Liliopsida: dioscoreaceae
A61P 35/00
Antineoplastic agents

Family

Application61/493,653Us provisional application · filed 6 Jun 2011

Application61/535,202Us provisional application · filed 15 Sep 2011

Application14/096,876Continuation · filed 4 Dec 2013

Application15/153,470Continuation

US 2014/0357608 A1Published application

US 9,340,572 B2Related patent

US 2016/0257707 A1This patent

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