US 2006/0052410 A1Published application

6H-[1]benzopyrano[4,3-b]quinolines and their use as estrogenic agents

AssigneeWyeth

InventorAn Vu

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Abstract

This invention provides 6H-[1]benzopyrano[4,3-b]quinoline compounds having the formula I: The invention further provides compositions including the compounds, methods for the use of the compounds, and methods of preparation of the compounds.

Claims61

Dependent claims

A compound of formula I having structure:

wherein:
A and A′ are each independently OH, H or OR;
each R is independently selected from the group consisting of C1-C6 alkyl, alkenyl, benzyl, acyl, aroyl, —C(═O)—OR′, sulfonyl and phosphoryl, wherein each R′ is independently selected from C1-C6 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, or C3-C10 cycloalkyl, each of which are optionally substituted by 1 to 3 substituents selected from C1-C6 alkyl or halogen;
R1 and R2 are independently selected from the group consisting of H, halogen, C1-C6 alkyl, C1-C6 perhaloalkyl, CF3, C2-C7 alkenyl and C1-C6 alkoxy;
R3, R4, R5 and R6 are each independently selected from the group consisting of H, halogen, CF3, C1-C6 perhaloalkyl, C1-C6 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, C3-C7 cycloalkyl, C1-C6 alkoxy, CN, —CHO, acyl, phenyl, aryl and heteroaryl;
wherein the alkyl or alkenyl moieties of R3, R4, R5 and R6 can each be optionally substituted with up to three substituents independently selected from halogen, OH, CN, trifluoroalkyl, trifluoroalkoxy, NO2 or phenyl, wherein said phenyl is optionally substituted with up to three independently selected R10 groups;
wherein the alkynyl moiety of R3, R4, R5 and R6 can each be optionally substituted with up to three substituents selected from halogen, —CN, —CHO, acyl, trifluoroalkyl, trialkylsilyl or phenyl, wherein said phenyl is optionally substituted with up to three independently selected R10 groups;
wherein the phenyl, aryl or heteroaryl moiety of R3, R4, R5 and R6 can each be optionally substituted with up to three substituents selected from halogen, —CN, alkyl, alkoxy, perfluoroalkyl or perfluoroalkoxy;
each R10 is independently selected from the group consisting of halogen, C1-C6 alkyl, C2-C7 alkenyl, —OH, C1-C6 alkoxy, —CN, —CHO, —NO2, amino, C1-C6 alkylamino, di-(C1-C6)alkylamino, thiol, and C1-C6 alkylthio;
and
n is 0, 1, 2, or 3;
provided that:
at least one of A and A′ is not H;
if n is 0, then R3 is not halogen;
and
at least one of R3, R4 and R5 is halogen, C1-C6 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, C3-C7 cycloalkyl, C1-C6 alkoxy, —CN, —CHO, acyl, phenyl, aryl or heteroaryl;
or an N-oxide thereof or a pharmaceutically acceptable salt thereof or a prodrug thereof.

14 more elements

A method for the preparation of a compound of Formula IV:

wherein:
A and A′are each independently OH, H or OR;
each R is independently selected from the group consisting of C1-C6 alkyl, alkenyl, benzyl, acyl, aroyl, —C(═O)—OR′, sulfonyl and phosphoryl, wherein each R′ is independently selected from C1-C6 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, or C3-C10 cycloalkyl, each of which are optionally substituted by 1 to 3 substituents selected from C1-C6 alkyl or halogen;
R1 and R2 are independently selected from the group consisting of H, halogen, C1-C6 alkyl, C1-C6 perhaloalkyl, CF3, C2-C7 alkenyl and C1-C6 alkoxy;
R3, R4, R5 and R6 are each independently selected from the group consisting of H, halogen, CF3, C1-C6 perhaloalkyl, C1-C6 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, C3-C7 cycloalkyl, C1-C6 alkoxy, CN, —CHO, acyl, phenyl, aryl and heteroaryl;
wherein the alkyl or alkenyl moieties of R3, R4, R5 and R6 can each be optionally substituted with up to three substituents independently selected from halogen, OH, CN, trifluoroalkyl, trifluoroalkoxy, NO2 or phenyl, wherein said phenyl is optionally substituted with up to three independently selected R10 groups;
wherein the alkynyl moiety of R3, R4, R5 and R6 can each be optionally substituted with up to three substituents selected from halogen, —CN, —CHO, acyl, trifluoroalkyl, trialkylsilyl or phenyl, wherein said phenyl is optionally substituted with up to three independently selected R10 groups;
wherein the phenyl, aryl or heteroaryl moiety of R3, R4, R5 and R6 can each be optionally substituted with up to three substituents selected from halogen, —CN, alkyl, alkoxy, perfluoroalkyl or perfluoroalkoxy;
each R10 is independently selected from the group consisting of halogen, C1-C6 alkyl, C2-C7 alkenyl, —OH, C1-C6 alkoxy, —CN, —CHO, —NO2, amino, C1-C6 alkylamino, di-(C1-C6)alkylamino, thiol, and C1-C6 alkylthio;
and
n is 0, 1, 2, or 3;
provided that:
at least one of A and A′ is not H;
if n is 0, then R3 is not halogen;
and
at least one of R3, R4 and R5 is halogen, C1-C6 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, C3-C7 cycloalkyl, C1-C6 alkoxy, —CN, —CHO, acyl, phenyl, aryl or heteroaryl;
or an N-oxide thereof or a pharmaceutically acceptable salt thereof or a prodrug thereof;
comprising the steps of:
r) providing a compound of Formula II:
and;
s) reacting the compound of Formula II with a compound of Formula III:
to produce the compound of Formula IV.

19 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/219,940Filed 6 Sep 2005
Priority: 7 Sep 2004
Published: 9 Mar 2006
Term ends: Not estimatedThe source records don’t support an estimate.

Classification39 codes

C07D 491/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 1/00
Drugs for disorders of the alimentary tract or the digestive system
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…

Family

Application60/607,766Us provisional application · filed 7 Sep 2004
US 7,354,927 B2Related patent
US 2006/0052410 A1This patent

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

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Abstract

A compound of formula I having structure:

wherein:
A and A′ are each independently OH, H or OR;
each R is independently selected from the group consisting of C1-C6 alkyl, alkenyl, benzyl, acyl, aroyl, —C(═O)—OR′, sulfonyl and phosphoryl, wherein each R′ is independently selected from C1-C6 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, or C3-C10 cycloalkyl, each of which are optionally substituted by 1 to 3 substituents selected from C1-C6 alkyl or halogen;
R1 and R2 are independently selected from the group consisting of H, halogen, C1-C6 alkyl, C1-C6 perhaloalkyl, CF3, C2-C7 alkenyl and C1-C6 alkoxy;
R3, R4, R5 and R6 are each independently selected from the group consisting of H, halogen, CF3, C1-C6 perhaloalkyl, C1-C6 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, C3-C7 cycloalkyl, C1-C6 alkoxy, CN, —CHO, acyl, phenyl, aryl and heteroaryl;
wherein the alkyl or alkenyl moieties of R3, R4, R5 and R6 can each be optionally substituted with up to three substituents independently selected from halogen, OH, CN, trifluoroalkyl, trifluoroalkoxy, NO2 or phenyl, wherein said phenyl is optionally substituted with up to three independently selected R10 groups;
wherein the alkynyl moiety of R3, R4, R5 and R6 can each be optionally substituted with up to three substituents selected from halogen, —CN, —CHO, acyl, trifluoroalkyl, trialkylsilyl or phenyl, wherein said phenyl is optionally substituted with up to three independently selected R10 groups;
wherein the phenyl, aryl or heteroaryl moiety of R3, R4, R5 and R6 can each be optionally substituted with up to three substituents selected from halogen, —CN, alkyl, alkoxy, perfluoroalkyl or perfluoroalkoxy;
each R10 is independently selected from the group consisting of halogen, C1-C6 alkyl, C2-C7 alkenyl, —OH, C1-C6 alkoxy, —CN, —CHO, —NO2, amino, C1-C6 alkylamino, di-(C1-C6)alkylamino, thiol, and C1-C6 alkylthio;
and
n is 0, 1, 2, or 3;
provided that:
at least one of A and A′ is not H;
if n is 0, then R3 is not halogen;
and
at least one of R3, R4 and R5 is halogen, C1-C6 alkyl, C2-C7 alkenyl, C2-C7 alkynyl, C3-C7 cycloalkyl, C1-C6 alkoxy, —CN, —CHO, acyl, phenyl, aryl or heteroaryl;
or an N-oxide thereof or a pharmaceutically acceptable salt thereof or a prodrug thereof.

14 more elements

Facts

Application

11/219,940Filed 6 Sep 2005

Priority

7 Sep 2004

Published

9 Mar 2006

Term ends

Not estimatedThe source records don’t support an estimate.

Classification39 codes

C07D 491/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 1/00
Drugs for disorders of the alimentary tract or the digestive system
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…