Compounds for the treatment of metabolic disorders

A biologically active agent, wherein the agent is a compound of the formula:

• 168
• wherein
• n is 1 or 2;
• t is 0 or 1;
• m is 0 and r is 1, or m is 1 and r is 0;
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound of formula II by a ring carbon;
• Z is
• 169
• R1 is hydrogen or alkyl having from 1 to 7 carbon atoms;
• R4 is hydrogen;
• —NHCOOC(CH3)3;
• —NHCH3;
• or —NHCH2CH3;
• or when R1 is hydrogen, a pharmaceutically acceptable salt of the compound.

A biologically active agent, wherein the agent is a compound of the formula:

• 172
• wherein
• n is 1 or 2;
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein one or both ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound of formula III by a ring carbon.

A biologically active agent, wherein the agent is a compound of the formula:

• 173
• wherein
• R1 is hydrogen or alkyl having from 1 to 7 carbon atoms;
• or when R1 is hydrogen, a pharmaceutically acceptable salt of the compound.

A biologically active agent, wherein the agent is a compound of the formula:

• 174
• wherein
• n is 1 or 2;
• R1 is hydrogen or alkyl having from 1 to 7 carbon atoms;
• R14 is hydroxy or hydrogen;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound of formula I by a ring carbon;
• or a pharmaceutically acceptable salt of the compound.

A biologically active agent, wherein the agent is a compound of the formula:

• 177
• wherein
• n is 1 or 2;
• R1 is hydrogen or alkyl having from 1 to 3 carbon atoms;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound of formula I by a ring carbon;
• or a pharmaceutically acceptable salt of the compound.

A biologically active agent, wherein the agent is a compound of the formula:

• 178
• wherein
• n is 1 or 2;
• R1 is hydrogen or alkyl having from 1 to 3 carbon atoms;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound of formula I by a ring carbon;
• or a pharmaceutically acceptable salt of the compound.

A biologically active agent, wherein the agent is a compound of the formula:

• 179
• wherein
• n is 0, 1 or 2;
• R1 is hydrogen or alkyl having from 1 to 3 carbon atoms;
• R15 is hydrogen or alkyl having from 1 to 3 carbon atoms;
• R9 is hydrogen, halo, hydroxy, or alkoxy having from 1 to 3 carbon atoms;
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound of formula I by a ring carbon;
• or a pharmaceutically acceptable salt of the compound.

A compound of the formula:

• 180
• wherein n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 181
• wherein m is 1;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 182
• wherein m is 1;
• n is I or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 183
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 184
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• R6 is alkyl having from 1 to 7 carbon atoms;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 185
• wherein n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 186
• wherein n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 187
• wherein n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 188
• wherein n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by I or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 189
• wherein Y1 is chloro;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 190
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 191
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 192
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• Y1 is chloro;
• n is I or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 193
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 194
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 195
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 196
• wherein n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 197
• wherein n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 198
• wherein n is 1 or 2;
• t is O or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having I or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 199
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 200
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 201
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 202
• wherein n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 203
• wherein R6 is alkyl having from 1 to 7 carbon atoms;
• n is 1 or 2;
• t is O or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 204
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 205
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• n is I or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, peifluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 206
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• Y1 is chloro;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A compound of the formula:

• 207
• wherein n is 1 or 2;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon.

A process for producing a compound of the formula:

• 208
• wherein R6 is alkyl having from 1 to 7 carbon atoms;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon, comprising, reacting a compound of the formula:
• 209
• with a compound of the formula BrCH2CO2R6 in the presence of a base, wherein
• R6, n, t and A are as above, to yield the corresponding compound of formula XI.

A process for producing a compound of the formula:

• 210
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• R6 is alkyl having from 1 to 7 carbon atoms;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon,
• comprising, reacting a compound of the formula:
• 211
• with a compound of the formula BrCH2CO2R6 in the presence of an alkali metal silyl amide, wherein R6, n, t and A are as above, to yield the corresponding compound of formula XXV.

A process for producing a compound of the formula:

• 212
• wherein n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon,
• comprising, reacting a compound of the formula:
• 213
• with the sodium salt of diethylacetamidomalonate, wherein n, t and A are as above,
• to yield the corresponding compound of formula XXVIII.

A process for producing a compound of the formula:

• 214
• wherein R1 is ethyl;
• n is 1 or 2;
• t is O or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon,
• comprising,
• a) reacting a compound of the formula:
• 215
• with either:
• i) a compound of formula A(CH2)t+n—OH under Mitsunobu conditions, or ii) a compound of formula A(CH2)t+n—Y, to yield the corresponding compound of the formula:
• 216
• wherein n, t and A are as above and Y is a leaving group
• b) hydrolyzing the compound of formula LXI to yield the corresponding compound of the formula:
• 217
• c) reacting the compound of formula LXII with thionyl chloride to yield the corresponding compound of the formula:
• 218
• wherein Y1 is chloro
• d) treating EtOCOCH2COOH with about two equivalents of butyllithium;
• and
• e) reacting the compound of formula LXIII with the product resulting from steps d), to yield the compound of formula LXV.

A process for producing a compound of the formula:

• 219
• wherein R1 is ethyl;
• R5 is alkyl having from 1 to 3 carbon atoms;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon,
• comprising,
• a) reacting a compound of the formula:
• 220
• with a compound of the formula:
• 221
• wherein Y1 is halo, and R5, n, and t are as above, to yield the corresponding compound of the formula:
• 222
• b) hydrolyzing the compound of formula LXVI to yield the corresponding compound of the formula:
• 223
• c) reacting the compound of formula LXVII with thionyl chloride to yield the corresponding compound of the formula:
• 224
• wherein Y1 is chloro
• d) treating EtO2CH2COOH with about two equivalents of butyllithium;
• and
• e) reacting the compound of formula LXVIII with the product resulting from step d), to yield the compound of formula LXIX.

A process for producing a compound of the formula:

• 225
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• n is I or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon,
• comprising,
• a) reacting a compound of the formula:
• 226
• with a compound of the formula:
• 227
• wherein Y1 is halo, and R5, n, t and A are as above, to yield the corresponding compound of the formula:
• 228
• b) treating the compound of formula XXIV with CuBr2 under selective bromination conditions to yield the compound of the formula:
• 229
• c) reacting the compound of formula LXX with the sodium salt of diethylacetamidomalonate to yield the compound of formula LXXI.

A process for producing a compound of the formula:

• 230
• wherein R1 is hydrogen;
• n is 1 or 2;
• t is O or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon,
• comprising,
• a) reacting a compound of the formula:
• 231
• with either:
• i) a compound of formula A(CH2)t+n—OH under Mitsunobu conditions, or ii) a compound of formula A(CH2)t+n—Y, to yield the corresponding compound of the formula:
• 232
• wherein n, t and A are as above and Y is a leaving group
• b) reacting the compound of formula LXXV with HBr to yield the corresponding compound of the formula:
• 233
• c) reacting the compound of formula LXXVI with the sodium salt of diethylacetamidomalonate to yield the corresponding compound of formula
• 234
• d) deesterifying the compound of formula LXXVII to yield the compound of formula LXXVIII.

A process for producing a compound of the formula:

• 236
• wherein R1 is hydrogen;
• R5 is alkyl having from 1 to 3 carbon atoms;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon,
• comprising,
• a) reacting a compound of the formula:
• 237
• with a compound of the formula:
• 238
• wherein R5, n, t and A are as above and Y1 is chioro, to yield the corresponding compound of the formula:
• 239
• b) reacting the compound of formula LXXX with HBr to yield the corresponding compound of the formula:
• 240
• c) reacting the compound of formula LXXXI with the sodium salt of diethylacetamidomalonate to yield the corresponding compound of formula
• 241
• d) deesterifying the compound of formula LXXXII to yield the compound of formula LXXXIII.

A process for producing a compound of the formula:

• 243
• wherein R6 is alkyl having from 1 to 7 carbon atoms;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon,
• comprising,
• a) reacting a compound of the formula:
• 244
• with either:
• i) a compound of formula A(CH2)t+n—OH under Mitsunobu conditions, or ii) a compound of formula A(CH2)t+n—Y, to yield the corresponding compound of the formula:
• 245
• wherein n, t and A are as above and Y is a leaving group
• b) reacting the compound of formula LXXV with Br—CH2—CO2R6, wherein
• R6 is as above, to yield the compound of formula LXXXV.

A process for producing the compound of the formula:

• 246
• wherein R1 is ethyl, R5 is alkyl having from 1 to 3 carbon atoms;
• m is 1;
• n is 1 or 2;
• t is 0 or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon,
• comprising
• a) reacting a compound of the formula:
• 247
• with a compound of the formula:
• 248
• wherein Y1 is chloro and m, n, t, R5 and A are as above, to yield the corresponding compound of the formula:
• 249
• b) hydrolyzing the compound of formula LXXXVI to yield the corresponding compound of the formula:
• 250
• c) reacting the compound of formula LXXXVII with thionyl chloride to yield the corresponding compound of the formula:
• 251
• wherein Y1 is chloro
• d) reacting the acid halide with Meldrum acid to yield the compound of forrnula LXXXIX.

A process for producing the compound of the formula:

• 252
• wherein R5 is alkyl having from 1 to 3 carbon atoms;
• R6 is alkyl having from 1 to 7 carbon atoms;
• n is 1 or 2;
• t is O or 1;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon,
• comprising
• a) reacting a compound of the formula:
• 253
• with Br—CH2—CO2R6, wherein R5, R6, n, t and A are as above, to yield the compound of formula XC.

A process for producing a compound of the formula:

• 254
• wherein n is 1 or 2;
• and
• A is phenyl, unsubstituted or substituted by 1 or 2 groups selected from:
• halo, alkyl having 1 or 2 carbon atoms, perfluoromethyl, alkoxy having 1 or 2 carbon atoms, and perfluoromethoxy;
• or cycloalkyl having from 3 to 6 ring carbon atoms wherein the cycloalkyl is unsubstituted or one or two ring carbons are independently mono-substituted by methyl or ethyl;
• or a 5 or 6 membered heteroaromatic ring having 1 or 2 ring heteroatoms selected from N, S and O and the heteroaromatic ring is covalently bound to the remainder of the compound by a ring carbon,
• comprising reacting a compound of the formula:
• 255
• wherein n and A are as above, with sodium azide in the presence of ammonium chloride in dimethylformamide to yield the corresponding compound of formula III.

A process for producing a compound of the formula:

• 256
• wherein R6 is alkyl having from 1 to 7 carbon atoms
• comprising reacting 2′, 6′-difluoroacetophenone with Br—CH2—CO2R6, wherein
• R6 is as above, to yield the compound of formula LVI.