| US 7,550,590 B2 | ||
| Dipeptidyl peptidase inhibitors | ||
| Jun Feng, Carlsbad, Calif. (US); Stephen L. Gwaltney, San Diego, Calif. (US); Stephen W. Kaldor, San Diego, Calif. (US); Jeffrey A. Stafford, San Diego, Calif. (US); Michael B. Wallace, San Diego, Calif. (US); and Zhiyuan Zhang, San Diego, Calif. (US) | ||
| Assigned to Takeda Pharmaceutical Company Limited, Osaka (Japan) | ||
| Filed on Mar. 24, 2004, as Appl. No. 10/809,635. | ||
| Claims priority of provisional application 60/457785, filed on Mar. 25, 2003. | ||
| Prior Publication US 2005/0004117 A1, Jan. 06, 2005 | ||
| This patent is subject to a terminal disclaimer. | ||
| Int. Cl. C07D 285/16 (2006.01); A61K 31/5395 (2006.01) | ||
| U.S. Cl. 544—283 [544/284; 544/292] | 16 Claims |
1. A compound of Formula XI:
 wherein
Q is selected from the group consisting of CO, CS, or C═NR9;
J, K, L, and M are each independently CR12 ;
R1 is -ZRm;
Z is selected from the group consisting of —CH2—, —CHR9—, —C(R9)(R9)—, —C(O)—, —C(S)—, —C(NH)—, —C(NR9)—, —O—, —N(H)—, —N(R9)—, and —S—;
Rm is selected from the group consisting of (2-cyano)phenyl, (3-cyano)phenyl, (2-hydroxy)phenyl, (3-hydroxy)phenyl, (2-alkenyl)phenyl,
(3-alkenyl)phenyl, (2-alkynyl)phenyl, (3-alkynyl)phenyl, (2-nitro)phenyl, (3-nitro)phenyl, (2-carboxy)phenyl, (3-carboxy)phenyl,
(2-carboxamido)phenyl, (3-carboxamido)phenyl, (2-sulfonamido)phenyl, (3-sulfonamido)phenyl, (2-tetrazolyl)phenyl, (3-tetrazolyl)phenyl,
(2-aminomethyl)phenyl, (3-aminomethyl)phenyl, (2-amino)phenyl, (3-amino)phenyl, (2-hydroxvmethyl)phenyl, (3-hydroxymethyl)phenyl,
(2-phenyl)phenyl, (3-phenyl)phenyl, (2-CONH2)phenyl, (3-CONH2)phenyl, (2-CONH(C1-7)alkyl)phenyl, (3-CONH(C1-7)alkyl)phenyl, (2-CO2(C1-7)alkyl)phenyl, and (3-CO2(C1-7)alkyl)phenyl, each substituted or unsubstituted;
R2 is selected from the group consisting of a 4, 5, 6 or 7 membered cycloalkyl or N- containing ring, the ring being substituted
with one or more substituents selected from the group consisting of alkyl, heteroalkyl, alkylene, alkylidene, amino, aminoalkyl,
aromatic, aryl, bicycloalkyl, bicycloaryl, carbamoyl, carbocyclyl, carboxyl, cycloalkyl, cycloalkylene, halo, heterobicycloalkyl,
heterocycloalkylene, heteroaryl, heterobicycloaryl, heterocycloalkyl, hydroxy, nitro, oxaalkyl, and oxoalkyl moieties, and
monovalent radicals derived from aldehydes, amides, esters, iminoketones and ketones;
each R9 is hydrogen or is selected from the group consisting of alkyl, cycloalkyl, heterocycloalkyl, arylalkyl, heteroarylalkyl, bicycloaryl,
and heterobicycloaryl, each being unsubstituted or substituted with one or more substituents selected from the group consisting
of alkyl, heteroalkyl, alkylene, alkylidene, amino, aminoalkyl, aromatic, aryl, bicycloalkyl, bicycloaryl, carbamoyl, carbocyclyl,
carboxyl, cycloalkyl, cycloalkylene, halo, heterobicycloalkyl, heterocycloalkylene, heteroaryl, heterobicycloaryl, heterocycloalkyl,
hydroxy, nitro, oxaalkyl, and oxoalkyl moieties, and monovalent radicals derived from aldehydes, amides, esters, iminoketones
and ketones; and
each R12 is hydrogen or is independently selected from the group consisting of halo, perhalo(C1-10)alkyl, CF3, alkyl, aryl, heteroaryl, aminosulfonyl, alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, aryloxy, heteroaryloxy, arylalkyl,
heteroarylalkyl, cycloalkyl, heterocycloalkyl, amino, thio, cyano, nitro, alkoxy, imine group, sulfonyl group and sulfinyl
group, and monovalent radicals derived from aldehydes, amides, esters, iminoketones and ketones, each being unsubstituted
or substituted with one or more substituents selected from the group consisting of alkyl, heteroalkyl, alkylene, alkylidene,
amino, aminoalkyl, aromatic, aryl, bicycloalkyl, bicycloaryl, carbamoyl, carbocyclyl, carboxyl, cycloalkyl, cycloalkylene,
halo, heterobicycloalkyl, heterocycloalkylene, heteroaryl, heterobicycloaryl, heterocycloalkyl, hydroxy, and monovalent radicals
derived from aldehydes, amides, esters, iminoketones and ketones.
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