US2013060027A1PendingUtilityA1
Tetrahydroisoquinolines and intermediates therefor
Est. expiryJun 4, 2028(~1.9 yrs left)· nominal 20-yr term from priority
Inventors:Paul LobbenRulin ZhaoBei WangBang-Chi ChenShuang LiuMin HuYuh-Lin Allen YangMatthew IsherwoodRasidul AminWenge Cui
A61P 43/00A61P 5/24A61P 25/04A61P 25/24A61P 25/30A61P 25/28A61P 25/22A61P 25/00A61P 25/34A61P 25/06A61P 3/04A61P 29/00A61P 25/14A61P 25/32A61P 3/00A61P 25/16A61P 13/02A61P 15/08A61P 13/10A61P 21/00A61P 15/10C07F 5/022C07C 223/02C07D 413/10C07C 215/20C07D 237/20C07D 217/04C07D 401/04C07C 217/58C07F 5/025C07F 5/04
56
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Abstract
Disclosed are processes for preparing tetrahydroisoquinolines, intermediates useful in the preparation of tetrahydroisoquinolines, processes for preparing such intermediates, and a crystalline form of 6-[(4S)-2-methyl-4-(naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine. Also disclosed are pharmaceutical compositions comprising tetrahydroisoquinolines, methods of using tetrahydroisoquinolines in the treatment of depression and other conditions and methods for obtaining the crystalline form.
Claims
exact text as granted — not AI-modified1 .- 18 . (canceled)
19 . A process of making a compound having the formula:
comprising reacting a compound having the formula;
where R 2 is selected from the group consisting of Br, H 3 CO and HO,
under conditions effective to promote the formation of a compound having the formula;
where R 3 is selected from
where R 4 is C 1 -C 4 alky, aryl or phenyl, and n is 1 or 2,
and reacting Compound 18R under conditions effective to promote the formation of compound rac-1.
20 . A process of making a compound having the formula:
comprising reacting a compound having the formula;
under conditions effective to promote the formation of a compound having the formula
and reacting compound 8 under conditions effective to promote the formation of Compound 2.
21 . (canceled)
22 . A process of making a compound having the formula:
comprising reacting a compound having the formula:
under conditions effective to promote the formation of compound rac-1.
23 . (canceled)
24 . A process of making a compound having the formula:
comprising reacting a compound having the formula;
under conditions effective to promote the formation of compound rac-1.
25 . A process of making a compound having the formula:
comprising reacting a compound having the formula
where each R 5 is selected from the group consisting of hydrogen, t-butoxycarbonyl, carboxybenzyl, para-methoxybenzylcarbonyl, para-methoxybenzyl, 2,4-dimethoxybenzyl, benzyl, 9-fluorenylmethyloxycarbonyl, N-phthalimide, COCH 3 and COCF 3 , under conditions effective to promote the formation of Compound 2.
26 . A process of making a compound having the formula:
comprising reacting a compound having the formula
where R 3 is selected from the group consisting of
where R 4 is C 1 -C 4 alky, aryl or phenyl, and n is 1 or 2, under conditions effective to promote the formation of compound rac-1.
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