US 10,399,931 B2Granted

Octahydroanthracene compound, preparation method and application thereof

AssigneesShandong Xinhua Pharmaceutical Co., Ltd., Shenyang Pharmaceutical University

InventorsGuoliang Chen, Zhonghui Zheng, Libo Zou, Daiming Zhang, Chunling Yuan, Fulong Ren, Xuefei Bao, Jinheng Gao, Linbo Zhou, Wuhong Fang

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Abstract

An octahydroanthracene compound having the structure shown in formula (I) and (II), preparation method and application thereof are disclosed. The octahydroanthracene compound has a good therapeutic effect on tumors and neurodegenerative diseases. The preparation of the octahydroanthracene compound is mainly carried out by using benzene as a starting material, and being subjected to Friedel-Crafts reaction, nitration, reduction, (sulfo-) amide formation, reduction, urea formation or amide formation, thus obtaining a target compound.

Claims14

Dependent claims

An octahydroanthracene compound or pharmaceutically acceptable salts of the octahydroanthracene compound, wherein structural formulas of the octahydroanthracene compound are shown in (I) or (II):

wherein X is H or C1-C6 alkyl group;
Linker is a substituted or unsubstituted C6-C10 aroyl or heteroaroyl group;
wherein a substituent of the substituted C6-C10 aroyl or heteroaroyl group is a C1-C6 alkyl group, a C1-C6 alkoxy group, a halogen, an amino group, a nitro group, a mercapto group, a thioether, a sulfone, a sulfoxide or an aminoalkoxy group;
or
the Linker is a substituted or unsubstituted phenyl group, pyridine, furan, pyrrole thiazole or thiophene;
wherein a substituent of the substituted phenyl group, pyridine, furan, pyrrole, thiazole or thiophene is a C1-C6 alkyl group or a C1-C6 alkoxy group;
R1 is hydrogen or C1-C6 alkyl group;
R is a nitrogen- or nitrogen-free structural fragment;
R2, R3 are hydrogen, nitrogen- or nitrogen-free structural fragments;
and wherein the nitrogen-free structural fragment is C1-C20 alkyl group;
a structure of the nitrogen-structural fragment is:
wherein the Linker1 of the structure of the nitrogen-structural fragment is a C2-C6 linear or branched alkyl group, and the NR4R5 is a primary amine or secondary amine.

9 more elements

An octahydroanthracene compound or pharmaceutically acceptable salts of the octahydroanthracene compound, selecting from:

4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] methyl benzoate;
4-[(1,1,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] benzoic acid;
N-hydroxy-4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl]benzamide;
N-(2-aminophenyl)-4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] benzamide;
N-[2-(N,N-diethylamino)]ethyl-4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] benzamide;
N-(2-amino) ethyl-4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] benzamide;
N-[2-(N,N-dimethyl amino)]ethyl-4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] benzamide;
N-(2-hydroxyphenyl)-4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] benzamide;
4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] aniline;
4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] ethyl phenylcarbamate;
4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl]phenylcarbamoyl-1-morpholine;
1-(2-aminophenyl)-3-{4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] phenyl} urea;
1-(2-amino) ethyl-3-{4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] phenyl} urea;
1-(2-hydroxy) ethyl-3-{4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] phenyl} urea;
1-(3-hydroxy)propyl-3-{4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] phenyl} urea;
N,N-dimethyl sulfonyl-4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] aniline;
1-(4-carboxypropyl)-3-{4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] phenyl} urea;
N-{4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl]phenylcarbamoyl}-4-piperidinyl formic acid;
4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] methyl phenylcarbamate;
1-(2-hydroxyphenyl)-3-{4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] phenyl} urea;
1-[2-(N,N-diethylamino)]ethyl-3-{4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] phenyl} urea;
1-[2-(N,N-dimethyl amino)]ethyl-3-{4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] phenyl} urea;
1-hydroxy-3-{4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl]phenyl} urea;
or
4-[(1,1,4,4,5,5,8,8-octamethyl-1,2,3,4,5,6,7,8-octahydro-9-anthryl) carbamoyl] phenyl carbamic acid-O-amino ester.

22 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/084,979Filed 23 Mar 2017
Priority: CN 2016 1 024772420 Apr 2016
Published: US 2019/0071393 A17 Mar 2019
Granted: 3 Sep 2019
Term ends: Not estimatedThe source records don’t support an estimate.

Classification27 codes

C07C 275/38
Having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton: being further substituted by…
A61K 31/167
Having aromatic rings, e.g. colchicine, atenolol, progabide: having the nitrogen of a carboxamide group directly attached to the aromatic ring,…
A61P 25/28
Drugs for disorders of the nervous system: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents,…
C07C 2/861
By condensation between a hydrocarbon and a non-hydrocarbon: the non-hydrocarbon contains only halogen as hetero-atoms