US2015191494A1PendingUtilityA1
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 5/24A61P 43/00A61P 3/00A61P 25/04A61P 25/34A61P 25/22A61P 25/28A61P 25/30A61P 25/32A61P 3/04A61P 29/00A61P 25/16A61P 25/14A61P 25/24A61P 25/00A61P 25/06A61P 15/10A61P 21/00A61P 15/08A61P 13/02A61P 13/10C07D 401/04C07F 5/025C07D 217/04C07D 237/20C07D 413/10C07C 215/20C07F 5/04C07C 217/58C07C 223/02C07F 5/022
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Claims
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-modifiedWhat is claimed is:
1 . A compound having the following formula:
where R 1 is selected from the group consisting of Br and H 3 CO.
2 . A compound of claim 1 having the following formula:
3 . A compound having the following formula:
where R 1 is selected from the group consisting of Br and H 3 CO.
4 . A compound of claim 3 having the following formula:
5 . A compound having the following formula:
where R 2 is selected from the group consisting of Br, H 3 CO and HO.
6 . A compound of claim 5 having the following formula:
7 . A compound having the following 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.
8 . A compound of claim 7 having the following formula
9 . A compound having the following formula:
Where each R 5 is independently 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 .
10 . A compound of claim 9 having the following formula:
11 . A compound having the following 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 .
12 . A compound of claim 11 having the following formula:
13 . A compound having the following 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 .
14 . A compound of claim 13 having the following formula:
15 . A compound having the following 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 , and X is selected from the group consisting of Cl, Br, I and trifluoromethanesulfonyloxy.
16 . A compound of claim 15 having the following formula:
17 . A process of making a compound having the formula:
where R 2 is selected from the group consisting of Br, H 3 CO and HO, comprising reacting a compound having the formula:
where R 1 is selected from Br or H 3 CO, under conditions effective to promote the formation of Compound 17R.
18 . 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 6.
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 . 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 28.
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 . 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 29.
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.
27 . A process of making a compound having the formula:
where R 6 is selected from the group consisting of C 1 -C 4 alkyl, benzyl, para-methoxybenzyl, 2,4-dimethoxybenzyl, 3,4-dimethoxybenzyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl, and triisopropylsilyl,
comprising reacting a compound of formula
under conditions effective to promote the formation of compound 7R.
28 . A process of making a compound having the formula:
where R 6 is selected from the group consisting of C 1 -C 4 alkyl, benzyl, para-methoxybenzyl, 2,4-dimethoxybenzyl, 3,4-dimethoxybenzyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl, and triisopropylsilyl,
comprising reacting a compound of formula
under conditions effective to promote the formation of compound 7R.
29 . A compound having the following formula:
where R 6 is selected from the group consisting of C 1 -C 4 alkyl, benzyl, para-methoxybenzyl, 2,4-dimethoxybenzyl, 3,4-dimethoxybenzyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl, and triisopropylsilyl.
30 . A compound according to claim 5 , wherein R 6 is CH 3 .
31 . A process of making a compound having the formula:
where R 6 is selected from the group consisting of C 1 -C 4 alkyl, benzyl, para-methoxybenzyl, 2,4-dimethoxybenzyl, 3,4-dimethoxybenzyl, tert-butyldimethylsilyl, tert-butyldiphenylsilyl, and triisopropylsilyl,
comprising reacting a compound of formula
under conditions effective to promote the formation of Compound 22R.
32 . A compound having the following formula:
where each R 5 is independently 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 .
33 . A compound of claim 32 having the following formula:Join the waitlist — get patent alerts
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