Taccalonolide microtubule stabilizers
US-2016257707-A1 · Sep 8, 2016 · US
Taccalonolide microtubule stabilizers
US10501490B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10501490-B2 |
| Application number | US-201715653397-A |
| Country | US |
| Kind code | B2 |
| Filing date | Jul 18, 2017 |
| Priority date | Jun 6, 2011 |
| Publication date | Dec 10, 2019 |
| Grant date | Dec 10, 2019 |
How to read this patent
A practical reading order for non-experts. Skip the full description unless you need deep technical detail.
- Title
What the patent document calls the invention.
- Abstract
A short plain-language summary of the technical disclosure.
- Assignees and inventors
Who owns or filed the patent and who is credited as inventor.
- Key dates
Filing, priority, publication, and grant dates set the timeline.
- First independent claim
The legal scope of protection — read this for what is actually claimed.
- CPC / IPC classifications
Technology tags used to group this patent with similar filings.
- Citations and related patents
Prior art links and similar publications in this corpus.
Abstract
Official abstract text for this publication.
The invention provides epoxytaccalonolide microtubule stabilizers and their use as anti-proliferative microtubule stabilizing agents.
First claim
Opening claim text (preview).
The invention claimed is: 1. A compound of the formula: wherein: ------ is present and is a single bond; R 1 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 in which one or more hydrogen atoms has been independently replaced by —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , or —S(O) 2 NH 2 ; R 2 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 in which one or more hydrogen atoms has been independently replaced by —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , or —S(O) 2 NH 2 , or R 2 is taken together with R 3 to form an epoxide at C-2/C-3; R 3 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 in which one or more hydrogen atoms has been independently replaced by —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , or —S(O) 2 NH 2 , or R 3 is taken together with R 2 as defined above; R 5 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 in which one or more hydrogen atoms has been independently replaced by —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , or —S(O) 2 NH 2 ; R 6 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 in which one or more hydrogen atoms has been independently replaced by —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , or —S(O) 2 NH 2 , or R 6 is taken together with R 7 to form an epoxide at C-6/C-7; R 6′ 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 in which one or more hydrogen atoms has been independently replaced by —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , or —S(O) 2 NH 2 ; R 7 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 in which one or more hydrogen atoms has been independently replaced by —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , or —S(O) 2 NH 2 , or oxo if R 7′ is not present, or R 7 is taken together with R 6 as defined above; R 7′ 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 in which one or more hydrogen atoms has been independently replaced by —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , or —S(O) 2 NH 2 ; R 11 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 in which one or more hydrogen atoms has been independently replaced by —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , or —S(O) 2 NH 2 ; R 12 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 in which one or more hydrogen atoms has been independently replaced by —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , or —S(O) 2 NH 2 ; R 15 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 in which one or more hydrogen atoms has been independently replaced by —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , or —S(O) 2 NH 2 ; R 20 is hydrogen, amino, cyano, azido, halo, hydroxy, hydroperoxy, 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 in which one or more hydrogen atoms has been independently replaced by —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , or —S(O) 2 NH 2 ; R 21 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 in which one or more hydrogen atoms has been independently replaced by —OH, —F, —Cl, —Br, —I, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH 3 , —N(CH 3 ) 2 , —C(O)NH 2 , —OC(O)CH 3 , or —S(O) 2 NH 2 ; R 25 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 in which one or more hydrogen atoms has been independently replaced by —OH, —F, —Cl, —Br, A, —NH 2 , —NO 2 , —CO 2 H, —CO 2 CH 3 , —CN, —SH, —OCH 3 , —OCH 2 CH 3 , —C(O)CH
Assignees
Inventors
Classifications
Antineoplastic agents · CPC title
Bridged systems · CPC title
- C07J71/001Primary
Oxiranes · CPC title
containing lactone rings, e.g. oxandrolone, bufalin · CPC title
Oxygen-containing hetero ring · CPC title
Patent family
Related publications grouped by family.
External sources
Frequently asked questions
Answers are generated from the same data shown on this page.
- What does patent US10501490B2 cover?
- The invention provides epoxytaccalonolide microtubule stabilizers and their use as anti-proliferative microtubule stabilizing agents.
- Who is the assignee on this patent?
- Univ Texas
- What technology area does this patent fall under?
- Primary CPC classification C07J71/001. Mapped technology areas include Chemistry & Metallurgy.
- When was this patent published?
- Publication date Tue Dec 10 2019 00:00:00 GMT+0000 (Coordinated Universal Time) (B2). Legal status and post-grant events are not shown on this page.
- What related patents are in patentsdb?
- We list 1 related publication on this page (citations in our corpus or others sharing the same primary CPC).