# US 9,434,740 B2 · Taxane compounds, compositions and methods

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- Number: US 9,434,740 B2
- Document ID: US9434740B2
- Status: Granted
- Kind: B2
- Application number: 14/325,960
- Filed: 2014-07-08
- Published: 2015-03-19
- Granted: 2016-09-06
- Earliest claimed: 2010-06-30
- Assignees: Odonate Therapeutics, LLC
- Applicants: Gfv, LLC
- Inventors: John K. Thottathil; Raymond P. Warrell
- Web page: https://patentgrep.com/patent/US9434740B2

## CPC

- C07D 493/08: Bridged systems
- A61P 35/00: Antineoplastic agents
- C07D 205/08: with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D 305/14: condensed with carbocyclic rings or ring systems
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 407/02: containing two hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention provides a method for the preparation of orally available pentacyclic taxane compounds, as well as intermediates useful in their preparation.

## Claims

### Claim 1

A method of making a compound, comprising coupling a taxane side chain precursor compound to a C-13 hydroxyl group of a compound of formula I
to produce a protected taxane reaction product, or a salt thereof.

### Claim 2

A compound having a structure of formula (II)
wherein Me is methyl and BOC is tert-butoxycarbonyl.

### Claim 3

A compound having a structure of formula (III)
wherein BOC is tert-butoxycarbonyl and R33 is a protected hydroxyl group.

### Claim 4 (depends on 3)

A method of synthesizing the compound of claim 3, comprising coupling a taxane side chain precursor compound having a formula
wherein R2 is an alkoxy group having from 1 to 6 carbon atoms or a halogen atom and R33 is a protected hydroxyl group to a C13 hydroxyl group of a compound having a structure of formula (I)
to produce a protected taxane reaction product having a structure of formula (III).

### Claim 5 (depends on 4)

The method of claim 4, wherein the C13 hydroxyl group is protected by a triisopropylsilyl (TIPS) or 2-methoxy propyl (MOP) group.

### Claim 6 (depends on 5)

The method of claim 5, wherein R2 is fluorine.

### Claim 7 (depends on 6)

The method of claim 6, wherein fluorine is at the 3-position of pyridine.

### Claim 8 (depends on 4)

The method of claim 4, wherein the side chain precursor compound has a formula
wherein Me is methyl and BOC is tert-butoxycarbonyl.

### Claim 9

A method of functionalizing a vinyl acetal, comprising: providing a compound having a structure of the formula
and oxidatively cleaving the terminal olefin group to form an aldehyde having the formula

### Claim 10 (depends on 9)

The method of claim 9, further comprising reductively aminating the aldehyde to provide a compound having the formula
and hydrogenating the C6-C7 double bond.

### Claim 11

A method of functionalizing a vinyl acetal, comprising:
providing a compound having the formula
and oxidatively cleaving the terminal olefin group to form an aldehyde having a structure of the formula

### Claim 12 (depends on 11)

The method of claim 11, further comprising reductively aminating the aldehyde.