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US 12,297,161 B2Granted
Process for making sarecycline hydrochloride
AssigneeAlmirall, S.A.
InventorsGiovanni Palombi, Eugenio Castelli, Giuseppe Motta, Meinrad Brenner, Ruiliang Lu, Shaozhi Huang, William Paul Armstrong, Gajanan Joshi, Farzaneh Seyedi, Sean Johnston
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Abstract
The described invention relates to sarecycline, related compounds, intermediates and salts thereof and processes for preparing the same.
Claims10
A process for preparing sarecycline hydrochloride of Formula (I)
- comprising:
- (a) reacting (4S,4aS,5aR,12aR)-4-(dimethylamino)-1,10,11,12a-tetrahydroxy-3, 12-dioxo-4a,5,5a,6-tetrahydro-4H-tetracene-2-carboxamide of Formula II
- with
- (i) trifluoroacetic acid (TFA);
- and
- (ii) N-iodosuccinimide (NIS);
- to form 7-iodosancycline trifluoroacetic acid salt of Formula III
- b) reacting the 7-iodosancycline trifluoroacetic acid salt of Formula (III) with
- (i) N-methyl pyrrolidone (NMP);
- (ii) triphenylphosphine (PPh3);
- (iii) Bis-(Triphenyl Phosphine) palladium chloride catalyst (BTPP—PdCl2);
- (iv) triethylsilane (Et3SiH);
- and
- (v) carbon monoxide (CO);
- to form 7-formylsancycline of Formula IV
- c) reacting the 7-formylsancycline of Formula IV with
- (i) dimethylhydroxylamine (DMHA) free base;
- (ii) oxalic acid;
- (iii) dimethylaminoborane (DMAB);
- and
- (iv) acetone
- to form sarecycline crude oxalate salt of Formula V
- d) reacting the sarecycline crude oxalate salt of Formula V with
- (i) ammonium hydroxide (NH3 (aqueous)) or hydrochloride acid (HCl);
- to form sarecycline free base of Formula VI
- (e) reacting the sarecycline free base of Formula VI with
- (i) ethanolic hydrochloric acid solution
- to form the sarecycline hydrochloride of Formula I.
25 more elements
Dependencies are inferred from the claim text.