Epelsiban

Epelsiban

557296
GSK-557296
GSK-557296-B

(3R,6R)-3-(2,3-Dihydro-1H-inden-2-yl)-1-[(1R)-1-(2,6-dimethyl-3-pyridinyl)-2-(4-morpholinyl)-2-oxoethyl]-6-[(1S)-1-methylpropyl]-2,5-piperazinedione

see..............http://newdrugapprovals.org/2015/01/04/epelsiban-being-developed-by-glaxosmithkline-for-the-treatment-of-premature-ejaculation-in-men/

see..............http://newdrugapprovals.org/2015/01/04/epelsiban-being-developed-by-glaxosmithkline-for-the-treatment-of-premature-ejaculation-in-men/

PAPER

J. Med. Chem., 2012, 55 (2), pp 783–796

DOI: 10.1021/jm201287w

http://pubs.acs.org/doi/abs/10.1021/jm201287w

(3R,6R)-3-(2,3-Dihydro-1H-inden-2-yl)-1-[(1R)-1-(2,6-dimethyl-3-pyridinyl)-2-(4-morpholinyl)-2-oxoethyl]-6-[(1S)-1-methylpropyl]-2,5-piperazinedione (69 EPELSIBAN)

A ………………………. gave colorless needles (75%)

mp 140 °C.

1H NMR (CDCl3) δ 7.49 (d, J =7.8 Hz, 1H, pyridyl-4H),

7.26–7.15 (m, 4H, indanyl-arylH),

7.10 (d, J =8.1 Hz, 1H, pyridyl-5H),

6.68 (s, 1H, NCHpyridyl),

6.49 (d, J = 2.8 Hz, 1H, lactam-NH),

4.10 (dd, J = 10.1 Hz, 4.0 Hz, 1H, NCHindanyl),

4.01 (d, J = 4.5 Hz, NCHsec-butyl),

3.75–2.71 (m, 13H, 8× morpholinyl-H, indanyl-3H, -1H, -2H),

2.62 and 2.58 (2s, 6H, pyridyl-2Me,-6Me),

1.64–1.52 (m, 1H, CHHMe),

0.98–0.79 (m, 2H, CHHMe, CHMeCH2),

0.70 (t, J = 7.1 Hz, 3H, CH2Me),

0.45 (d, J = 6.8 Hz, 3H, CHMe).

LCMS m/z 519 (MH+) single component, gradient 2 (tR 2.70 min).

HRMS calcd for C30H38N4O4(MH+) 519.29658, found 519.29667.

HPLC: 100% (tR 10.388 min).

benzenesulfonic acid;(3R,6R)-6-[(2S)-butan-2-yl]-3-(2,3-dihydro-1H-inden-2-yl)-1-[(1R)-1-(2,6-dimethylpyridin-3-yl)-2-morpholin-4-yl-2-oxoethyl]piperazine-2,5-dione,CAS 1159097-48-9

UNII-H629P9T4UN, GSK557296B, Epelsiban besylate (USAN), Epelsiban besylate [USAN], 1159097-48-9, H629P9T4UN

EPELSIBAN BESYLATE SALT

To a ……………………………….give the besylate (3.214 g, 92.6%) as white crystals of 69B

mp 179–183 °C.

1H NMR (CD3OD) δ 8.30 (d, 1H, J = 8.1 Hz, pyridyl-4H),

7.84–7.80 (m, 2H, PhSO3– 2× ortho-H),

7.78 (d, J = 8.3 Hz, 1H, pyridyl-5H),

7.45–7.38 (m, 3H, PhSO3– 2×meta-H, para-H),

7.23–7.09 (m, 4H, indanyl-arylH),

6.08 (broad s, 1H, NCHpyridyl),

4.00 (d, J =4.6 Hz, 1H, NCHsec-butyl),

3.92 (d, J = 9.9 Hz, 1H, NCHindanyl),

3.78–3.39 and 3.14–2.80 (m, 13H, 8× morpholinyl-H, indanyl-3H, -1H, -2H)),

2.79 and 2.78 (2s, 6H, pyridyl-2Me, -6Me),

1.85–1.74 (m, 1H, CHHMe),

1.59–1.48 (m, 1H, CHHMe),

1.15–1.01 (m, 1H, CHMeCH2),

0.92 (d, J =6.3 Hz, 3H, CHMe),

0.85 (t, J = 7.3 Hz, 3H, CH2Me).

LCMS m/z 519 MH+ single components, tR2.72 min;

circular dichroism (CH3CN) λmax 225.4 nm, dE −15.70, E15086; λmax 276 nm, dE 3.82, E5172.

HRMS calcd for C30H38N4O4 (MH+) 519.2971, found 519.2972.

Anal. (C30H38N4O4·C6H6O3S·3.0H2O) C, H, N, S.

see..............http://newdrugapprovals.org/2015/01/04/epelsiban-being-developed-by-glaxosmithkline-for-the-treatment-of-premature-ejaculation-in-men/

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