US 5,710,287 AGranted

Taxanes having an amino substituted side-chain and pharmaceutical compositions containing them

AssigneeFlorida State University

InventorsRobert A. Holton, Hossain Nadizadeh, Kasthuri Rengan, Chunlin Tao

Life of this patent

Estimating the term…

Abstract

Taxane derivatives having an amino substituted C13 side chain.

Claims34

Dependent claims

A taxane having the formula ##STR47## wherein X.sub.1 is --OX.sub.6, --SX.sub.7, or --NX.sub.8 X.sub.9 ;

X.sub.2 is hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
or substituted or unsubstituted aryl or heteroaryl;
X.sub.3 and X.sub.4 are independently hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
or substituted or unsubstituted aryl or heteroaryl;
X.sub.5 is --CONX.sub.8 X.sub.10 ;
X.sub.6 is hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
substituted or unsubstituted aryl or heteroaryl;
or hydroxy protecting group;
X.sub.7 is substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
substituted or unsubstituted aryl or heteroaryl;
or sulfhydryl protecting group;
X.sub.8 is hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
or substituted or unsubstituted aryl or heteroaryl;
X.sub.9 is an amino protecting group;
X.sub.10 is substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
or substituted or unsubstituted aryl or heteroaryl;
R.sub.1 is hydroxy, protected hydroxy or together with R.sub.14 forms a carbonate;
R.sub.2 is hydroxy or --OCOR.sub.31 ;
R.sub.4a is hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
substituted or unsubstituted aryl or heteroaryl;
cyano;
hydroxy;
or --OCOR.sub.30 ;
R.sub.7a is hydrogen, halogen, or --OR.sub.28 ;
R.sub.9 is hydrogen or together with R.sub.9a forms an oxo;
R.sub.9a is hydrogen, hydroxy, protected hydroxy, acyloxy, or together with R.sub.9 forms an oxo;
R.sub.10 is hydrogen or together with R.sub.10a forms an oxo,
R.sub.10a is hydrogen, --OCOR.sub.29, hydroxy, or protected hydroxy, or together with R.sub.10 forms an oxo;
R.sub.14 is hydrogen, hydroxy, protected hydroxy or together with R.sub.1 forms a carbonate;
R.sub.28 is hydrogen, acyl, or hydroxy protecting group;
and
R.sub.29, R.sub.30, and R.sub.31 are independently hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
or substituted or unsubstituted monocyclic aryl or monocyclic heteroaryl.

44 more elements

A taxane having the formula ##STR48## wherein X.sub.1 is --OX.sub.6, --SX.sub.7, or --NX.sub.8 X.sub.9 ;

X.sub.2 is hydrogen;
substituted, unsubstituted, straight, branch chained or cyclic alkyl;
substituted, unsubstituted, straight or branch chained alkenyl or alkynyl;
or substituted or unsubstituted aryl or heteroaryl;
X.sub.3 and X.sub.4 are independently hydrogen;
substituted, unsubstituted, straight, branch chained or cyclic alkyl;
substituted, unsubstituted, straight or branch chained alkenyl or alkynyl;
or substituted or unsubstituted aryl or heteroaryl;
X.sub.5 is --CONX.sub.8 X.sub.10 ;
X.sub.6 is hydrogen;
substituted, unsubstituted, straight, branch chained or cyclic alkyl;
substituted, unsubstituted, straight or branch chained alkenyl or alkynyl;
substituted or unsubstituted aryl or heteroaryl;
or hydroxy protecting group;
X.sub.7 is substituted, unsubstituted, straight, branch chained or cyclic alkyl;
substituted, unsubstituted, straight or branch chained alkenyl or alkynyl;
substituted or unsubstituted aryl or heteroaryl;
or sulfhydryl protecting group;
X.sub.8 is hydrogen;
substituted, unsubstituted, straight, branch chained or cyclic alkyl;
substituted, unsubstituted, straight or branch chained alkenyl or alkynyl;
or substituted or unsubstituted aryl or heteroaryl;
X.sub.9 is an amino protecting group;
X.sub.10 is substituted, unsubstituted, straight or branch chained alkenyl or alkynyl;
substituted or unsubstituted aryl or heteroaryl;
or alkyl, wherein said alkyl is substituted or unsubstituted methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, sec-butyl, isobutyl, cyclobutyl, pentyl or hexyl;
R.sub.1 is hydroxy, protected hydroxy or together with R.sub.14 forms a carbonate;
R.sub.2 is hydroxy or --OCOR.sub.31 ;
R.sub.4a is hydrogen;
substituted, unsubstituted, straight, branch chained or cyclic alkyl;
substituted, unsubstituted, straight or branch chained alkenyl or alkynyl;
substituted or unsubstituted aryl or heteroaryl;
cyano;
hydroxy;
or --OCOR.sub.30 ;
R.sub.7a is hydrogen, halogen, or --OR.sub.28 ;
R.sub.9 is hydrogen or together with R.sub.9a forms an oxo;
R.sub.9a is hydrogen, hydroxy, protected hydroxy, acyloxy, or together with R.sub.9 forms an oxo;
R.sub.10 is hydrogen or together with R.sub.10a forms an oxo,
R.sub.10a is hydrogen, --OCOR.sub.29, hydroxy, or protected hydroxy, or together with R.sub.10 forms an oxo;
R.sub.14 is hydrogen, hydroxy, protected hydroxy or together with R.sub.1 forms a carbonate;
R.sub.28 is hydrogen, acyl, or hydroxy protecting group;
and
R.sub.29, R.sub.30, and R.sub.31 are independently hydrogen;
substituted, unsubstituted, straight, branch chained or cyclic alkyl;
substituted, unsubstituted, straight or branch chained alkenyl or alkynyl;
or substituted or unsubstituted monocyclic aryl or monocyclic heteroaryl.

44 more elements

A taxane having the formula ##STR49## wherein X.sub.1 is --OX.sub.6, --SX.sub.7, or --NX.sub.8 X.sub.9 ;

X.sub.2 is hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
or substituted or unsubstituted aryl or heteroaryl;
X.sub.3 and X.sub.4 are independently hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
substituted or unsubstituted heteroaryl;
or substituted aryl;
X.sub.5 is --CONX.sub.8 X.sub.10 ;
X.sub.6 is hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
substituted or unsubstituted aryl or heteroaryl;
or hydroxy protecting group;
X.sub.7 is substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
substituted or unsubstituted aryl or heteroaryl;
or sulfhydryl protecting group;
X.sub.8 is hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
or substituted or unsubstituted aryl or heteroaryl;
X.sub.9 is an amino protecting group;
X.sub.10 is substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
or substituted or unsubstituted aryl or heteroaryl;
R.sub.1 is hydroxy, protected hydroxy or together with R.sub.14 forms a carbonate;
R.sub.2 is hydroxy or --OCOR.sub.31 ;
R.sub.4a is hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
substituted or unsubstituted aryl or heteroaryl;
cyano;
hydroxy;
or --OCOR.sub.30 ;
R.sub.7a is hydrogen, halogen, or --OR.sub.28 ;
R.sub.9 is hydrogen or together with R.sub.9a forms an oxo;
R.sub.9a is hydrogen, hydroxy, protected hydroxy, acyloxy, or together with R.sub.9 forms an oxo;
R.sub.10 is hydrogen or together with R.sub.10a forms an oxo,
R.sub.10a is hydrogen, --OCOR.sub.29, hydroxy, or protected hydroxy, or together with R.sub.10 forms an oxo;
R.sub.14 is hydrogen, hydroxy, protected hydroxy or together with R.sub.1 forms a carbonate;
R.sub.28 is hydrogen, acyl, or hydroxy protecting group;
and
R.sub.29, R.sub.30, and R.sub.31 are independently hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
or substituted or unsubstituted monocyclic aryl or monocyclic heteroaryl.

45 more elements

Dependencies are inferred from the claim text.

Facts

Application: 08/462,122Filed 5 Jun 1995 · continuation
Priority: 23 Sep 1991
Granted: 20 Jan 1998
Term ends: Not estimatedThe source records don’t support an estimate.

Classification15 codes

C07D 407/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
C07C 227/22
Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton: from lactams, cyclic ketones or cyclic oximes,…
C07C 231/12
Preparation of carboxylic acid amides: by reactions not involving the formation of carboxamide groups
C07C 233/87
With the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom: of a carbon skeleton…

Family

Serial763,805Parent of this continuation-in-part · filed 23 Sep 1991
Serial862,955Parent of this continuation-in-part · filed 3 Apr 1992
Serial862,819Parent of this continuation-in-part · filed 3 Apr 1992
Serial863,849Parent of this continuation-in-part · filed 6 Apr 1992
Serial949,107Parent of this continuation-in-part · filed 22 Sep 1992
Serial34,247Parent of this continuation-in-part · filed 22 Mar 1993
Serial34,852Parent of this continuation-in-part · filed 22 Mar 1993
Serial94,566Parent of this continuation · filed 20 Jul 1993
US 5,430,160 AParent of this continuation-in-part
US 5,227,400 AParent of this continuation-in-part
US 5,710,287 AThis patent

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

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A taxane having the formula ##STR47## wherein X.sub.1 is --OX.sub.6, --SX.sub.7, or --NX.sub.8 X.sub.9 ;

X.sub.2 is hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
or substituted or unsubstituted aryl or heteroaryl;
X.sub.3 and X.sub.4 are independently hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
or substituted or unsubstituted aryl or heteroaryl;
X.sub.5 is --CONX.sub.8 X.sub.10 ;
X.sub.6 is hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
substituted or unsubstituted aryl or heteroaryl;
or hydroxy protecting group;
X.sub.7 is substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
substituted or unsubstituted aryl or heteroaryl;
or sulfhydryl protecting group;
X.sub.8 is hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
or substituted or unsubstituted aryl or heteroaryl;
X.sub.9 is an amino protecting group;
X.sub.10 is substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
or substituted or unsubstituted aryl or heteroaryl;
R.sub.1 is hydroxy, protected hydroxy or together with R.sub.14 forms a carbonate;
R.sub.2 is hydroxy or --OCOR.sub.31 ;
R.sub.4a is hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
substituted or unsubstituted aryl or heteroaryl;
cyano;
hydroxy;
or --OCOR.sub.30 ;
R.sub.7a is hydrogen, halogen, or --OR.sub.28 ;
R.sub.9 is hydrogen or together with R.sub.9a forms an oxo;
R.sub.9a is hydrogen, hydroxy, protected hydroxy, acyloxy, or together with R.sub.9 forms an oxo;
R.sub.10 is hydrogen or together with R.sub.10a forms an oxo,
R.sub.10a is hydrogen, --OCOR.sub.29, hydroxy, or protected hydroxy, or together with R.sub.10 forms an oxo;
R.sub.14 is hydrogen, hydroxy, protected hydroxy or together with R.sub.1 forms a carbonate;
R.sub.28 is hydrogen, acyl, or hydroxy protecting group;
and
R.sub.29, R.sub.30, and R.sub.31 are independently hydrogen;
substituted, unsubstituted, straight, branched chain or cyclic alkyl;
substituted, unsubstituted, straight or branched chain alkenyl or alkynyl;
or substituted or unsubstituted monocyclic aryl or monocyclic heteroaryl.

44 more elements

Facts

Application

08/462,122Filed 5 Jun 1995 · continuation

Priority

23 Sep 1991

Granted

20 Jan 1998

Term ends

Not estimatedThe source records don’t support an estimate.

Classification15 codes

C07D 407/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links
C07C 227/22
Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton: from lactams, cyclic ketones or cyclic oximes,…
C07C 231/12
Preparation of carboxylic acid amides: by reactions not involving the formation of carboxamide groups
C07C 233/87
With the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom: of a carbon skeleton…

Family

Serial763,805Parent of this continuation-in-part · filed 23 Sep 1991

Serial862,955Parent of this continuation-in-part · filed 3 Apr 1992

Serial862,819Parent of this continuation-in-part · filed 3 Apr 1992

Serial863,849Parent of this continuation-in-part · filed 6 Apr 1992

Serial949,107Parent of this continuation-in-part · filed 22 Sep 1992

Serial34,247Parent of this continuation-in-part · filed 22 Mar 1993

Serial34,852Parent of this continuation-in-part · filed 22 Mar 1993

Serial94,566Parent of this continuation · filed 20 Jul 1993

US 5,430,160 AParent of this continuation-in-part

US 5,227,400 AParent of this continuation-in-part

US 5,710,287 AThis patent

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