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Generated: July 23, 2017

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Claims for Patent: 9,242,986

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Claims for Patent: 9,242,986

Title:Synthesis of carbamoylpyridone HIV integrase inhibitors and intermediates
Abstract: A synthesis approach providing an early ring attachment via a bromination to compound 1-1 yielding compound II-II, whereby a final product such as AA can be synthesized. In particular, the 2,4-difluorophenyl-containing sidechain is attached before creation of the additional ring Q. ##STR00001##
Inventor(s): Kawasuji; Takashi (Osaka, JP), Nagamatsu; Daiki (Osaka, JP)
Assignee: SHIONOGI & CO., LTD. (Osaka, JP) ViiV Healthcare Company (Research Triangle Park, NC)
Application Number:14/272,823
Patent Claims: 1. A crystal form of a sodium salt of a compound of formula AA ##STR00039## having characteristic diffraction peaks at 6.4.degree..+-.0.2.degree., 9.2.degree..+-.0.2.degree., 13.8.degree..+-.0.2.degree., 19.2.degree..+-.0.2.degree. and 21.8.degree..+-.0.2.degree. degrees two-theta in an X-ray powder diffraction pattern.

2. The crystal form according to claim 1, having characteristic diffraction peaks at 6.4.degree..+-.0.2.degree., 9.2.degree..+-.0.2.degree., 13.8.degree..+-.0.2.degree., 14.6.degree..+-.0.2.degree., 15.2.degree..+-.0.2.degree., 17.6.degree..+-.0.2.degree., 19.2.degree..+-.0.2.degree., 21.8.degree..+-.0.2.degree., 24.1.degree..+-.0.2.degree. and 28.7.degree..+-.0.2.degree. degrees two-theta in an X-ray powder diffraction pattern.

3. The crystal form according to claim 1, having characteristic infrared absorption spectra at 1641 cm.sup.-1.+-.2 cm.sup.-1, 1536 cm.sup.-1.+-.2 cm.sup.-1, 1503 cm.sup.-1.+-.2 cm.sup.-1 and 1424 cm.sup.-1.+-.2 cm.sup.-1.

4. A crystal form of a sodium salt of a compound of formula AA ##STR00040## having characteristic infrared absorption spectra at 1641 cm.sup.-1.+-.2 cm.sup.-1, 1536 cm.sup.-1.+-.2 cm.sup.-1, 1503 cm.sup.-1.+-.2 cm.sup.-1 and 1424 cm.sup.-1.+-.2 cm.sup.-1.

5. The crystal form according to claim 4, having characteristic infrared absorption spectra at 1641 cm.sup.-1.+-.2 cm.sup.-1 1536 cm.sup.-1.+-.2 cm.sup.-1, 1503 cm.sup.-1.+-.2 cm.sup.-1, 1424 cm.sup.-1.+-.2 cm.sup.-1, 1282 cm.sup.-1.+-.2 cm.sup.-1, 1258 cm.sup.-1.+-.2 cm.sup.-1, 1093 cm.sup.-1.+-.2 cm.sup.-1 and 1069 cm.sup.-1.+-.2 cm.sup.-1.

6. A crystal form of a sodium salt of a compound of formula AA ##STR00041## having one or more spectra selected from the group consisting of (a) to (c): (a) X-ray powder diffraction pattern substantially as shown in FIG. 1; (b) Infrared absorption spectra substantially as shown in FIG. 2; and (c) Solid state .sup.13C-NMR spectra substantially as shown in FIG. 3.

7. A crystal form of a hydrate of a sodium salt of a compound of formula AA ##STR00042## having characteristic diffraction peaks at 8.0.degree..+-.0.2.degree., 9.3.degree..+-.0.2.degree., 11.3.degree..+-.0.2.degree., 16.0.degree..+-.0.2.degree., and 22.8.degree..+-.0.2.degree. degrees two-theta in an X-ray powder diffraction pattern.

8. The crystal form according to claim 7, having characteristic diffraction peaks at 8.0.degree..+-.0.2.degree., 9.3.degree..+-.0.2.degree., 11.3.degree..+-.0.2.degree., 15.4.degree..+-.0.2.degree., 16.0.degree..+-.0.2.degree., 18.7.degree..+-.0.2.degree., 19.1 .degree..+-.0.2.degree., 19.8.degree..+-.0.2.degree., 22.8.degree..+-.0.2.degree. and 26.8.degree..+-.0.2.degree. degrees two-theta in an X-ray powder diffraction pattern.

9. The crystal form according to claim 7, having characteristic infrared absorption spectra at 1637 cm.sup.-1.+-.2 cm.sup.-1, 1536 cm.sup.-1.+-.2 cm.sup.-1, 1501 cm.sup.-1.+-.2 cm.sup.-1 and 1422 cm-.sup.1.+-.2 cm.sup.-1.

10. A crystal form of a hydrate of a sodium salt of a compound of formula AA ##STR00043## having characteristic infrared absorption spectra at 1637 cm.sup.-1.+-.2 cm.sup.-1, 1536 cm.sup.-1.+-.2 cm.sup.-1, 1501 cm.sup.-1.+-.2 cm.sup.-1 and 1422 cm-.sup.1.+-.2 cm.sup.-1.

11. The crystal form according to claim 10, having one or more spectra selected from the group consisting of (d) and (e): (d) X-ray powder diffraction pattern substantially as shown in FIG. 4; and (e) Infrared absorption spectra substantially as shown in FIG. 5.

12. A crystal form of a hydrate of a sodium salt of a compound of formula AA ##STR00044## having one or more spectra selected from the group consisting of (d) and (e): (d) X-ray powder diffraction pattern substantially as shown in FIG. 4; and (e) Infrared absorption spectra substantially as shown in FIG. 5.
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Federal Trade Commission
Queensland Health
Accenture
Harvard Business School
Argus Health
Colorcon
AstraZeneca
Mallinckrodt
Chinese Patent Office
Johnson and Johnson

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