IP Library › Patent Application 11714689
Patent Application
App. No. 11/714,689

Dihydropyrancarboxamides and uses thereof

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Patent No.
US None
App. No.
11/714,689
Abstract

The present invention provides novel dihydropyrancarboxamide compounds of formula (I): and collections of these compounds, and provides methods for the synthesis of these compounds; wherein R 1 -R 6 are as defined herein. Additionally, the present invention provides pharmaceutical compositions and methods for treating disorders such as proliferative diseases, and cancer, to name a few.

Claims (43)

1 . A compound having the structure:

wherein R 1 , R 2 and R 4 are each independently hydrogen or an aliphatic, heteroaliphatic, aryl, heteroaryl, alkylaryl or alkylheteroaryl moiety;

R 3 is hydrogen or an aliphatic, heteroaliphatic alkylaryl, heteroaryl or alkylheteroaryl moiety;

R 5 and R 6 are each independently hydrogen or an aliphatic, heteroaliphatic, aryl, heteroaryl, alkylaryl, or alkylheteroaryl moiety, and wherein R 6 and R 7 , taken together, may form a cyclic aliphatic, heteroaliphatic, aliphatic(aryl), heteroaliphatic(aryl), aliphatic(heteroaryl) or heteroaliphatic(heteroaryl) moiety, or an aryl or heteroaryl moiety;

wherein each of the foregoing aliphatic and heteroaliphatic moieties may be substituted or unsubstituted, cyclic or acyclic, saturated or unsaturated or linear or branched; and each of the foregoing aryl, heteroaryl, alkylaryl or alkylheteroaryl moieties may be substituted or unsubstituted; and

pharmaceutically acceptable derivatives thereof.

2 . The compound of claim 1 , wherein the compound has the structure (II):

wherein R 1 , R 2 and R 4 are each independently hydrogen or an aliphatic, heteroaliphatic, aryl, heteroaryl, alkylaryl or alkylheteroaryl moiety;

R 3 is hydrogen or an aliphatic, heteroaliphatic, alkylaryl, heteroaryl or alkylheteroaryl moiety;

R 5 and R 6 are each independently hydrogen or an aliphatic, heteroaliphatic, aryl, heteroaryl, alkylaryl, or alkylheteroaryl moiety, and wherein R 6 and R 7 , taken together, may form a cyclic aliphatic, heteroaliphatic, aliphatic(aryl), heteroaliphatic(aryl), aliphatic(heteroaryl) or heteroaliphatic(heteroaryl) moiety, or an aryl or heteroaryl moiety;

wherein each of the foregoing aliphatic and heteroaliphatic moieties may be substituted or unsubstituted, cyclic or acyclic, saturated or unsaturated or linear or branched; and each of the foregoing aryl, heteroaryl, alkylaryl or alkylheteroaryl moieties may be substituted or unsubstituted; and

pharmaceutically acceptable derivatives thereof.

3 . The compound of claim 1 , wherein R 1 is hydrogen or an alkyl, heteroalkyl, aryl or heteroaryl moiety substituted with Z, wherein Z is hydrogen, —(CH 2 ) q OR Z , —(CH 2 ) q SR Z , —(CH 2 ) q N(R Z ) 2 , —(C═O)R Z , —(C═O)N(R Z ) 2 , or an aliphatic, heteroaliphatic, aryl, heteroaryl, -(aliphatic)aryl, -(aliphatic)heteroaryl, -(heteroaliphatic)aryl, or -(heteroaliphatic)heteroaryl moiety, wherein q is 0-4, and wherein each occurrence of R Z is independently hydrogen, a protecting group, a solid support unit, or an aliphatic, heteroaliphatic, aryl, heteroaryl, -(aliphatic)aryl, -(aliphatic)heteroaryl, -(heteroaliphatic)aryl, or -(heteroaliphatic)heteroaryl moiety; wherein each of the foregoing alkyl or heteroalkyl moieties may be substituted or unsubstituted, linear or branched, cyclic or acyclic, saturated or unsaturated; and wherein each of the foregoing aryl, heteroaryl, -(alkyl)aryl, -(alkyl)heteroaryl, -(heteroalkyl)aryl, or -(heteroalkyl)heteroaryl moieties may be substituted or unsubstituted.

4 . The compound of claim 3 , wherein R 1 is hydrogen, lower alkyl, a substituted or unsubstituted phenyl or -(lower alkyl)phenyl moiety, —(CH 2 ) n OR z , —[(CH 2 ) n O] m R z , —(CH 2 ) n —Ar—(CH 2 ) m OR z ; wherein n and m are each independently integers from 1-6, Ar represents a substituted or unsubstituted aryl or heteroaryl moiety, and R z is independently hydrogen, a protecting group, a solid support unit, or an aliphatic, heteroaliphatic, aryl, heteroaryl, -(aliphatic)aryl, -(aliphatic)heteroaryl, -(heteroaliphatic)aryl, or -(heteroaliphatic)heteroaryl moiety; wherein each of the foregoing alkyl or heteroalkyl moieties may be substituted or unsubstituted, linear or branched, cyclic or acyclic, saturated or unsaturated; and wherein each of the foregoing aryl, heteroaryl, -(alkyl)aryl, -(alkyl)heteroaryl, -(heteroalkyl)aryl, or -(heteroalkyl)heteroaryl moieties may be substituted or unsubstituted.

5 . The compound of claim 4 , wherein R 1 is hydrogen, ethyl, or has one of the structures:

wherein R z is as defined in claim 4 .

6 . The compound of claim 1 , wherein R 2 is hydrogen or an alkyl, heteroalkyl, aryl or heteroaryl moiety substituted with Z, wherein Z is hydrogen, —(CH 2 ) q OR Z , —(CH 2 ) q SR Z , —(CH 2 ) q N(R Z ) 2 , —(C═O)R Z , —(C═O)N(R Z ) 2 , or an aliphatic, heteroaliphatic, aryl, heteroaryl, -(aliphatic)aryl, -(aliphatic)heteroaryl, -(heteroaliphatic)aryl, or -(heteroaliphatic)heteroaryl moiety, wherein q is 0-4, and wherein each occurrence of R z is independently hydrogen, a protecting group, a solid support unit, or an aliphatic, heteroaliphatic, aryl, heteroaryl, -(aliphatic)aryl, -(aliphatic)heteroaryl, -(heteroaliphatic)aryl, or -(heteroaliphatic)heteroaryl moiety; wherein each of the foregoing alkyl or heteroalkyl moieties may be substituted or unsubstituted, linear or branched, cyclic or acyclic, saturated or unsaturated; and wherein each of the foregoing aryl, heteroaryl, -(alkyl)aryl, -(alkyl)heteroaryl, -(heteroalkyl)aryl, or -(heteroalkyl)heteroaryl moieties may be substituted or unsubstituted.

7 . The compound of claim 6 , wherein R 2 is hydrogen, lower alkyl, a substituted or unsubstituted phenyl or -(lower alkyl)phenyl moiety, —(CH 2 ) n OR z , —[(CH 2 ) n O] m R z , —(CH 2 ) n —Ar—(CH 2 ) m OR z ; wherein n and m are each independently integers from 1-6, Ar represents a substituted or unsubstituted aryl or heteroaryl moiety, and R z is independently hydrogen, a protecting group, a solid support unit, or an aliphatic, heteroaliphatic, aryl, heteroaryl, -(aliphatic)aryl, -(aliphatic)heteroaryl, -(heteroaliphatic)aryl, or -(heteroaliphatic)heteroaryl moiety; wherein each of the foregoing alkyl or heteroalkyl moieties may be substituted or unsubstituted, linear or branched, cyclic or acyclic, saturated or unsaturated; and wherein each of the foregoing aryl, heteroaryl, -(alkyl)aryl, -(alkyl)heteroaryl, -(heteroalkyl)aryl, or -(heteroalkyl)heteroaryl moieties may be substituted or unsubstituted.

8 . The compound of claim 6 , wherein R 2 is hydrogen or has one of the structures:

wherein R z is as defined in claim 6 .

9 . The compound of claim 1 , wherein R 3 is an alkyl, heteroalkyl, heteroaryl, -(alkyl)aryl, -(alkyl)heteroaryl, -(heteroalkyl)aryl, or -(heteroalkyl)heteroaryl moiety; wherein each of the foregoing alkyl or heteroalkyl moieties may be substituted or unsubstituted, linear or branched, cyclic or acyclic, saturated or unsaturated; and wherein each of the foregoing heteroaryl, -(alkyl)aryl, -(alkyl)heteroaryl, -(heteroalkyl)aryl, or -(heteroalkyl)heteroaryl moieties may be substituted or unsubstituted.

10 . The compound of claim 9 , wherein R 3 has one of the structures:

11 . The compound of claim 1 , wherein R 4 is hydrogen or an alkyl heteroalkyl, aryl, heteroaryl, -(alkyl)aryl, -(alkyl)heteroaryl, -(heteroalkyl)aryl, or -(heteroalkyl)heteroaryl moiety; wherein each of the foregoing alkyl or heteroalkyl moieties may be substituted or unsubstituted, linear or branched, cyclic or acyclic, saturated or unsaturated; and wherein each of the foregoing aryl, heteroaryl, -(alkyl)aryl, -(alkyl)heteroaryl, -(heteroalkyl)aryl, or -(heteroalkyl)heteroaryl moieties may be substituted or unsubstituted.

12 . The compound of claim 11 , wherein R 4 is hydrogen alkyl or heteroalkyl.

13 . The compound of claim 1 , wherein R 5 and R 6 are each independently hydrogen or an alkyl, heteroalkyl, aryl, heteroaryl, -(alkyl)aryl, -(alkyl)heteroaryl, -(heteroalkyl)aryl, or -(heteroalkyl)heteroaryl moiety; or wherein R 5 and R 6 , taken together, form a substituted or unsubstituted, saturated or unsaturated cyclic moiety comprising 5-12 carbon atoms, 0-5 oxygen atoms, 0-5 sulfur atoms and 1-5 nitrogen atoms; and wherein each of the foregoing alkyl or heteroalkyl moieties may be substituted or unsubstituted, linear or branched, cyclic or acyclic, saturated or unsaturated; and wherein each of the foregoing aryl, heteroaryl, -(alkyl)aryl, -(alkyl)heteroaryl, -(heteroalkyl)aryl, or -(heteroalkyl)heteroaryl moieties may be substituted or unsubstituted.

14 . The compound of claim 1 , wherein —NR 5 R 6 is one of the following the structures:

15 . (canceled)

16 . (canceled)

17 . (canceled)

18 . The compound of claim 1 having the structure:

19 . The compound of claim 1 having the structure:

20 . The compound of claim 1 having the structure:

21 . The compound of claim 1 having the structure:

22 . (canceled)

23 . A library of compounds comprising a plurality of library members, wherein at least two library members are a compound of claim 1 .

24 . (canceled)

25 . (canceled)

26 . The library of claim 23 , wherein the library comprises at least 100 compounds.

27 . The library of claim 23 , wherein the library comprises at least 1,000 compounds.

28 . The library of claim 23 , wherein the library comprises at least 2,000 compounds.

29 . The library of claim 23 , wherein the library comprises at least 10,000 compounds.

30 . A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier.

31 - 39 . (canceled)

Assignments (1)
SECURITY AGREEMENT Recorded Jul 29, 2026
From: PLAID INC.
To: BARCLAYS BANK PLC
Reel/Frame 076082/0108 →