C11 oxymyl and hydroxylamino prostaglandins useful as FP agonists

A method of treating a human or other animal subject having a bone disorder, said method comprising administering to said subject a compound according to the structure:

• wherein
• (a) R1 is CO2H, C(O)NHOH, CO2R7, CH2OH, S(O)2R7, C(O)NHR7, C(O)NHS(O)2R7, or tetrazole;
• wherein R7 is alkyl, heteroalkyl, monocyclic carbocyclic aliphatic ring, monocyclic heterocyclic aliphatic ring, monocyclic aromatic ring, or monocyclic heteroaromatic ring;
• (b) W is O, NH, S, S(O), S(O)2, or (CH2)m;
• wherein m is an integer from 0 to about 3;
• (c) R2 is H and R3 is H or lower alkyl, or R2 and R3 together form a covalent bond;
• (d) R4 is H, alkyl, heteroalkyl, monocyclic carbocyclic aliphatic ring, monocyclic heterocyclic aliphatic ring, monocyclic aromatic ring, or monocyclic heteroaromatic ring;
• (e) each R5 is independently selected from the group consisting of H, CH3, and C2H5;
• (f) X is NHR8 or OR8, wherein each R8 is independently selected from the group consisting of H, acyl, alkyl, heteroalkyl, monocyclic carbocyclic aliphatic ring, monocyclic heterocyclic aliphatic ring, monocyclic aromatic ring, and monocyclic heteroaromatic ring;
• (g) each R6 is independently selected from the group consisting of H, CH3, C2H5, OR8, and NHR8;
• (h) Y is O, NHR8, S, S(O), or S(O)2, provided no carbon has more than one heteroatom attached to it;
• (i) Z is H, methyl, monocyclic carbocyclic aliphatic ring, monocyclic heterocyclic aliphatic ring, monocyclic aromatic ring, monocyclic heteroaromatic ring, bicyclic carbocyclic aliphatic ring, bicyclic heterocyclic aliphatic ring, bicyclic aromatic ring, or bicyclic heteroaromatic ring, provided that when Y is S, S(O), or S(O)2 and Z is H, q is at least 1;
• (j) a and b are independently selected from the group consisting of single bond, cis double bond, and trans double bond;
• (k) p is an integer from 1 to 5, q is an integer from 0 to 5, and p+q is 1 to 5;
• and
• any optical isomer, diastereomer, enantiomer of the above structure or a pharmaceutically-acceptable salt, or bio-hydrolyzable amide, ester, or imide thereof.

A method of treating glaucoma, said method comprising administering to a human or other animal a safe and effective amount of a compound according to the structure:

• wherein
• (a) R1 is CO2H, C(O)NHOH, CO2R7, CH2OH, S(O)2R7, C(O)NHR7, C(O)NHS(O)2R7, or tetrazoie;
• wherein R7 is alkyl, heteroalkyl, monocyclic carbocyclic aliphatic ring, monocyclic heterocyclic aliphatic ring, monocyclic aromatic ring, or monocyclic heteroaromatic ring;
• (b) W is O, NH, S, S(O), S(O)2, or (CH2)m;
• wherein m is an integer from 0 to about 3;
• (c) R2 is H and R3 is H or lower alkyl, or R2 and R3 together form a covalent bond;
• (d) R4 is H, alkyl, heteroalkyl, monocyclic carbocyclic aliphatic ring, monocyclic heterocyclic aliphatic ring, monocyclic aromatic ring, or monocyclic heteroaromatic ring;
• (e) each R5 is independently selected from the group consisting of H, CH3, and C2H5;
• (f) X is NHR8 or OR8, wherein each R8 is independently selected from the group consisting of H, acyl, alkyl, heteroalkyl, monocyclic carbocyclic aliphatic ring, monocyclic heterocyclic aliphatic ring, monocyclic aromatic ring, and monocyclic heteroaromatic ring;
• (g) each R6 is independently selected from the group consisting of H, CH3, C2H5, OR8, and NHR8;
• (h) Y is O, NHR8, S, S(O), or S(O)2, provided no carbon has more than one heteroatom attached to it;
• (i) Z is H, methyl, monocyclic carbocyclic aliphatic ring, monocyclic heterocyclic aliphatic ring, monocyclic aromatic ring, monocyclic heteroaromatic ring, bicyclic carbocyclic aliphatic ring, bicyclic heterocyclic aliphatic ring, bicyclic aromatic ring, or bicyclic heteroaromatic ring, provided that when Y is S, S(O), or S(O)2 and Z is H, q is at least 1;
• (j) a and b are independently selected from the group consisting of single bond, cis double bond, and trans double bond;
• (k) p is an integer from 1 to 5, q is an integer from 0 to 5, and p+q is 1 to 5;
• and
• any optical isomer, diastereomer, enantiomer of the above structure or a pharmaceutically-acceptable salt, or bio-hydrolyzable amide, ester, or imide thereof.