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US 8,552,187 B2Granted
Processes and intermediates for carbamoylpyridone HIV integrase inhibitors
AssigneesShionogi & Co., Ltd., ViiV Healthcare Company
InventorsBrian Alvin Johns, Maosheng Duan, Toshikazu Hakogi
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Abstract
Processes are provided which create an aldehyde methylene, or hydrated or hemiacetal methylene attached to a heteroatom of a 6 membered ring without going through an olefinic group and without the necessity of using an osmium reagent. In particular, a compound of formula (I) can be produced from (II) and avoid the use of an allyl amine: (formulae I and II) where R, P1 P3, R3 and Rx are as described herein.
Claims6
A compound of the following formula (V):
- wherein
- P1 is H or a hydroxyl protecting group;
- P3 is H or a carboxy protecting group;
- R3 is H, halogen, hydroxy, optionally substituted lower alkyl, optionally substituted cycloalkyl, optionally substituted lower alkenyl, optionally substituted lower alkoxy, optionally substituted lower alkenyloxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heterocyclic group, optionally substituted heterocycleoxy or optionally substituted amino;
- Rx is H, halo or R2—X—NR1—C(O)—;
- R2 is optionally substituted aryl;
- X is a single bond, a heteroatom group selected from O, S, SO, SO2, and NH or lower alkylene or lower alkenylene wherein each may be intervened by the heteroatom;
- R1 is H or lower alkyl;
- and
- R5 and R6 are independently lower alkyl or R5 and R6 can be alkyl and joined to form a 5-, 6-, or 7-membered ring.
7 more elements
A compound of the following formula (VI):
- wherein
- P1 is H or a hydroxyl protecting group;
- P3 is H or a carboxy protecting group;
- R3 is H, halogen, hydroxy, optionally substituted lower alkyl, optionally substituted cycloalkyl, optionally substituted lower alkenyl, optionally substituted lower alkoxy, optionally substituted lower alkenyloxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heterocyclic group, optionally substituted heterocycleoxy or optionally substituted amino;
- Rx is R2—X—NR1—C(O)—;
- R2 is optionally substituted aryl;
- X is a single bond, a heteroatom group selected from O, S, SO, SO2, and NH or lower alkylene or lower alkenylene wherein each may be intervened by the heteroatom;
- and
- R1 is H or lower alkyl.
6 more elements
A compound of the following formula (I):
- wherein
- R is —CH(OH)(OCH3);
- P1 is —Bn;
- P3 is —CH3;
- R3 is —H;
- and
- Rx is Br.
4 more elements
A compound of the following formula (I):
- wherein
- R is —CH(OH)2;
- P1 is H or a hydroxyl protecting group;
- P3 is H or a carboxy protecting group;
- R3 is H, halogen, hydroxy, optionally substituted lower alkyl, optionally substituted cycloalkyl, optionally substituted lower alkenyl, optionally substituted lower alkoxy, optionally substituted lower alkenyloxy, optionally substituted aryl, optionally substituted aryloxy, optionally substituted heterocyclic group, optionally substituted heterocycleoxy or optionally substituted amino;
- R1 is H or lower alkyl;
- Rx is R2—X—NR1—C(O)—;
- R2 is optionally substituted aryl;
- and
- X is a single bond, a heteroatom group selected from O, S, SO, SO2, and NH or lower alkylene or lower alkenylene wherein each may be intervened by the heteroatom.
7 more elements
Dependencies are inferred from the claim text.