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Details for Patent: 8,624,023

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Details for Patent: 8,624,023

Title:Synthesis of carbamoylpyridone HIV integrase inhibitors and intermediates
Abstract: A synthesis approach providing an early ring attachment via a bromination to compound I-I yielding compound II-II: ##STR00001## whereby a final product such as AA: ##STR00002## can be synthesized. In particular, the 2,4-difluorophenyl-containing sidechain is attached before creation of the additional ring Q.
Inventor(s): Yoshida; Hiroshi (Osaka, JP), Taoda; Yoshiyuki (Osaka, JP), Johns; Brian (Research Triangle Park, NC), Kawasuji; Takashi (Osaka, JP), Nagamatsu; Daiki (Osaka, JP)
Assignee: Shionogi & Co., Ltd. (Osaka, JP) ViiV Healthcare Company (Research Triangle Park, NC)
Filing Date:Dec 08, 2009
Application Number:13/128,992
Claims:1. A process of for the preparation of a pyridone compound of formula (AA), (BB) or (CC): ##STR00039## comprising the steps of: P-1) brominating a compound of the following formula (I-I) to produe a bromine compound of the following formula (II-II): ##STR00040## wherein R is --CHO, --CH(OH).sub.2, --CH(OH)(OR.sup.4), --CH(OH)--CH.sub.2OH or --CH(OR.sup.5)(OR.sup.6); P.sup.1 is H or a hydroxyl protecting group; P.sup.3 is H or a carboxy protecting group; R.sup.4 is lower alkyl; R.sup.5 and R.sup.6 are independently lower alkyl or R.sup.5 and R.sup.6 can be alkyl and joined to form a 5-, 6-, or 7-membered ring, and P-2) creating the 2,4-di-fluorophenyl-CH.sub.2--NH--C(O)-- sidechain with the reactants 2,4-di-fluorophenyl-CH.sub.2--NH.sub.2 and carbon monoxide.

2. A process is provided for the preparation of a pyridone compound of the following formula (AA), (BB) or (CC): ##STR00041## comprising the steps of: P-1) brominating a compound of the following formula (I-I) to produce a bromine compound of the following formula (II-II): ##STR00042## wherein R is --CHO, --CH(OH).sub.2, --CH(OH)(OR.sup.4), --CH(OH)--CH.sub.2OH or --CH(OR.sup.5)(OR.sup.6); P.sup.1 is H or a hydroxyl protecting group; P.sup.3 is H or a carboxy protecting group; R.sup.4 is lower alkyl; R.sup.5 and R.sup.6 are independently lower alkyl or R.sup.5 and R.sup.6 can be lower alkyl and joined to form a 5-, 6-, or 7-membered ring, P-2) creating the 2,4-di-fluorophenyl-CH.sub.2--NH--C(O)-- sidechain with the reactants 2,4-di-fluorophenyl-CH.sub.2--NH.sub.2 and carbon monoxide to form a compound of formula III-III: ##STR00043## P-3) condensing and debenzylating a compound of formula III-III to form a compound of formula AA, BB, or CC.

3. The process according to claim 1, wherein said step P-2) is carried out before creation of the Q ring.

4. The process according to claim 1, wherein said pyridone compound is of the formula AA.

5. The process according to claim 1, wherein said pyridone compound is of the formula BB.

6. The process according to claim 1, wherein said pyridone compound is of the formula CC.

7. The process according to claim 1, wherein said step P-2) is carried out after creation of the Q ring.

8. The process according to claim 7, wherein said pyridone compound is of the formula AA.

9. The process of claim 7, wherein said pyridone compound is of the formula BB.

10. The process of claim 7, wherein said pyridone compound is of the formula CC.

11. A process according to claim 1 wherein P.sup.1 is benzyl; P.sup.3 is methyl; and R is --CHO, --CH(OH)(OR.sup.4), --CH(OR.sup.5)(OR.sup.5) wherein R.sup.4 and R.sup.5 are lower alkyl.
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