Heat shock protein 90 inhibitors

1. Compounds of the Formula II:

wherein A is hydrogen, halogen, lower alkyl, lower alkoxy, aryl, aralyl, allyl, or together with B and the atoms to which they are attached form a heterocyclic ring having 4 to 12 ring members with at least one heteroatom selected from oxygen, nitrogen, or sulfur;

wherein B is hydroxy, amino, halogen, lower alkoxy, aralkoxy, or together with A and the atoms to which they are attached form a heterocyclic ring having 4 to 12 ring members with at least one heteroatom selected from oxygen, nitrogen, or sulfur;

wherein C is hydroxy, amino, or lower alkoxy;

wherein D is hydroxy, lower alkyl, lower alkoxy, amino, or together with M and the carbon atoms to which they are attached and the carbon at position 2 form a carbocyclic ring having 5 to 8 ring members;

wherein E is hydroxy, halogen, lower alkoxy, amino, allyl amine, or together with F and the atoms to which they are attached form a heterocyclic ring having 4 to 12 ring members with at least one heteroatom selected from oxygen, nitrogen, or sulfur;

wherein F is hydroxy, halogen, thiol, lower alkoxy, amino, oxidized to form a ketone, or together with E and the atoms to which they are attached form a heterocyclic ring having 4 to 12 ring members with at least one heteroatom selected from oxygen, nitrogen, or sulfur;

wherein G is hydrogen, halogen, amino, thiol, hydroxy, lower alkyl, lower alkoxy, oxidized to form a ketone, or together with I, J, and M, and the carbon atoms to which G and I are attached form a heterocycle ring having 5 to 8 ring members with at least one heteroatom selected from oxygen, nitrogen, or sulfur;

wherein I is alkyl, amino, carbonyl, sulfanyl, sulfenyl, sulfonyl, oxygen, or together with G, J, and M, and the carbon atoms to which G and I are attached form a heterocycle ring having 5 to 8 ring members with at least one heteroatom selected from oxygen, nitrogen, or sulfur;

wherein J is alkyl, amino, carbonyl, sulfanyl, sulfenyl, sulfonyl, oxygen, or together with I, M, and G, and the carbon atoms to which G and I are attached form a heterocycle ring having 5 to 8 ring members with at least one heteroatom selected from oxygen, nitrogen, or sulfur; and

wherein M is alkyl, cycloalkyl; or M together with I, J, and G and the carbons to which G and I are attached form a heterocycle ring having 5 to 8 ring members with at least one heteroatom selected from oxygen, nitrogen, or sulfur; or M together with D and the carbon atoms to which they are attached form a heterocylic ring having 4 to 12 ring members with at least one heteroatom selected from oxygen, nitrogen, and sulfur; or M is alkyl and together with I, J, and G and the carbons to which G and I are attached form a heterocycle ring having 5 to 8 ring members with at least one heteroatom selected from oxygen, nitrogen, or sulfur; or M is alkyl and together with D and the carbon atoms to which they are attached form a heterocylic ring having 4 to 12 ring members with at least one heteroatom selected from oxygen, nitrogen, and sulfur.

2. The compounds according to claim 1 corresponding to Formula II(B):

wherein A is hydrogen, chlorine, fluorine, methyl, phenyl, benzyl, or allyl;

wherein B is hydroxy, chlorine, fluorine, methoxy, ethoxy, or benzyloxy;

wherein C is hydroxy, methoxy, or amino comprising —NH 2 ;

wherein D is hydroxy, methoxy, ethoxy, or amino comprising —NH 2 , —NHCH 3 , or —N(CH 3 ) 2 ;

wherein E is hydroxy, chlorine, fluorine, methoxy, ethoxy, amino comprising —NH 2 , or allyl amine comprising —NHCHCH═CH 2 ;

wherein F is hydroxy, chlorine, fluorine, methoxy, ethoxy, amino, thiol, or is oxidized to form a ketone; and

wherein G is hydrogen, hydroxy, methyl, methoxy, ethoxy, or oxidized to form a ketone.

3. The compounds according to claim 1 corresponding to Formula II(C):

wherein A is hydrogen, chlorine, fluorine, methyl, phenyl, benzyl, or allyl;

wherein B is hydroxy, chlorine, fluorine, methoxy, ethoxy, or benzyloxy;

wherein C is hydroxy, methoxy, ethoxy, or amino comprising —NH 2 ;

wherein D is hydroxy, methoxy, ethoxy, or amino comprising —NH 2 , —NHCH 3 , or —N(CH 3 ) 2 ;

wherein E is hydroxy, chlorine, fluorine, methoxy, ethoxy, amino comprising —NH 2 , or allyl amine comprising —NHCHCH═CH 2 ; and

wherein F is hydroxy, chlorine, fluorine, methoxy, ethoxy, amino comprising —NH 2 , thiol, or is oxidized to form a ketone.

4. The compounds according to claim 1 corresponding to Formula II(D):

wherein A is hydrogen, chlorine, fluorine, methyl, phenyl, benzyl, or allyl;

wherein B is hydroxy, chlorine, fluorine, methoxy, ethoxy, or benzyloxy;

wherein C is hydroxy, methoxy, ethoxy, or amino comprising —NH 2 ;

wherein D is hydroxy, methoxy, ethoxy, or amino comprising —NH 2 , —NHCH 3 , or —N(CH 3 ) 2 ;

wherein E is hydroxy, chlorine, fluorine, methoxy, ethoxy, amino comprising —NH 2 , or allyl amine comprising —NHCHCH═CH 2 ;

wherein F is hydroxy, chlorine, fluorine, methoxy, ethoxy, amino, thiol, or is oxidized to form a ketone;

wherein G is hydrogen, hydroxy, methyl, methoxy, ethoxy, or is oxidized to form a ketone;

wherein I is amino comprising —NH— or —NCH 3 —, lower alkyl comprising —CH 2 —, carbonyl, sulfanyl, or oxygen; and

wherein J is carbonyl, amino, lower alkyl, sulfanyl, or oxygen.

5. The compounds according to claim 1 corresponding to Formula II(E):

wherein A is hydrogen, chlorine, fluorine, methyl, phenyl, benzyl, or allyl;

wherein B is hydroxy, chlorine, fluorine, methoxy, ethoxy, or benzyloxy;

wherein C is hydroxy, methoxy, ethoxy, or amino comprising —NH 2 ;

wherein D is hydroxy, methoxy, ethoxy, or amino comprising —NH 2 , —NHCH 3 , or —N(CH 3 ) 2 ;

wherein E is hydroxy, chlorine, fluorine, methoxy, ethoxy, amino comprising —NH 2 , or allyl amine comprising —NHCHCH═CH 2 ;

wherein F is hydroxy, chlorine, fluorine, methoxy, ethoxy, amino, thiol, or is oxidized to form a ketone; and

wherein G is hydrogen, hydroxy, methyl, methoxy, ethoxy, or oxidized to form a ketone.

6. The compounds according to claim 1 , corresponding to Formula II(F):

wherein A is hydrogen, chlorine, fluorine, methyl, phenyl, benzyl, or allyl;

wherein B is hydroxy, chlorine, fluorine, methoxy, ethoxy, or benzyloxy;

wherein C is hydroxy, methoxy, ethoxy, or amino comprising —NH 2 ;

wherein D is hydroxy, methoxy, ethoxy, or amino comprising —NH 2 , —NHCH 3 , or —N(CH 3 ) 2 ;

wherein E and F together with the atoms to which they are attached together form a heterocyclic ring having 5 to 10 ring members with at least one heteroatom selected from oxygen, nitrogen, or sulfur; and

wherein G is hydrogen, hydroxy, methyl, methoxy, or ethoxy.

7. The compounds according to claim 1 , corresponding to Formula II(G):

wherein A and B together with the atoms to which they are attached together form a heterocyclic ring having 4 to 10 members with at least one heteroatom selected from oxygen, nitrogen, or sulfur;

wherein C is hydroxy, methoxy, ethoxy, or —NH 2 ;

wherein D is hydroxy, methoxy, ethoxy, —NH 2 , —NHCH 3 , or —N(CH 3 ) 2 ;

wherein E is hydroxy, chlorine, fluorine, methoxy, ethoxy, —NH 2 , or —NHCHCH═CH 2 ;

wherein F is hydroxy, chlorine, fluorine, methoxy, ethoxy, —NH 2 , thiol, or is oxidized to form a ketone; and

wherein G is hydrogen, hydroxy, methyl, methoxy, ethoxy, or is oxidized to form a ketone.

8. The compounds according to claim 1 ,

wherein A is hydrogen, chlorine, fluorine, methyl, phenyl, benzyl, or allyl;

wherein B is hydroxy, chlorine, fluorine, methoxy, ethoxy, or benzyloxy;

wherein C is hydroxy, methoxy, ethoxy, or —NH 2 ;

wherein D and M together with the carbon atoms to which they are attached and the carbon at position 2 form a carbocyclic ring having 5 to 8 ring members; or M is alkyl and M together with D and the carbon atoms to which they are attached form a heterocylic ring having 4 to 12 ring members with at least one heteroatom selected from oxygen, nitrogen, and sulfur;

wherein E is hydroxy, chlorine, fluorine, methoxy, ethoxy, —NH 2 , or —NHCHCH═CH 2 ;

wherein F is hydroxy, chlorine, fluorine, methoxy, ethoxy, —NH 2 , thiol, or is oxidized to form a ketone; and

wherein G is hydrogen, hydroxy, methyl, methoxy, ethoxy or is oxidized to form a ketone.

9. The compounds according to claim 8 , corresponding to either one of the Formulas II(H) or II(I) below: