US 9,309,254 B2Granted

Pyrimidinyl-diazospiro compounds

AssigneeConvergence Pharmaceuticals Limited

InventorsGerard M. P. Giblin, David T. MacPherson, David R. Witty, Steven J. Stanway

Life of this patent

Estimating the term…

Abstract

The invention relates to spiro derivatives, to the use of said derivatives in treating diseases and conditions mediated by modulation of voltage-gated sodium channels, to compositions containing said derivatives and processes for their preparation.

Claims24

Dependent claims

A compound of formula (I) or a pharmaceutically acceptable salt thereof:

wherein:
Ring A represents a phenyl ring, a 5- or 6-membered aromatic heterocyclic ring or a 5- to 12-membered aromatic or non-aromatic bicyclic heterocyclic group;
n represents an integer selected from 0 to 4;
each R1 independently represents C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, -Z—C3-6 cycloalkyl, halogen, haloC1-6 alkyl, C1-6 alkoxy, haloC1-6 alkoxy, -Z-phenyl, -Z-Het, —CN, —CONR6R7, —NR6R7, -Z—C1-3 alkyl, wherein said Het group represents a 5- or 6-membered aromatic heterocyclic ring or a 4- to 7-membered non-aromatic heterocyclic ring, wherein said phenyl or Het group of R1 may be optionally substituted by one or more R8 groups and wherein n represents an integer greater than 1, said R1 groups represent no more than one -Z-phenyl or one -Z-Het group;
Z represents a bond or a linker selected from —O—, —CH2—, —CH2—O— or —O—CH2—;
R6 and R7 independently represent hydrogen or C1-6 alkyl or R6 and R7 together with the nitrogen atom to which they are attached join to form a 4- to 7-membered nitrogen containing non-aromatic heterocyclic ring;
R8 represents C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, halogen, haloC1-6 alkyl, C1-6 alkoxy, haloC1-6 alkoxy, —CN or -NR6R7;
m represents an integer selected from 0 to 2;
each R2 independently represents C1-6 alkyl, C2-6 alkenyl, C2-6 alkynyl, halogen, haloC1-6 alkyl, C1-6 alkoxy, haloC1-6 alkoxy, —CN or —NR7R8;
R3 represents hydrogen or C1-6 alkyl;
R4 represents hydrogen or C1-6 alkyl;
p represents an integer from 0 to 3;
each R5 independently represents C1-3 alkyl or fluoro;
Y represents —CH2— or —(CH2)2—;
q represents an integer selected from 0 to 2;
and
R9 represents C1-3 alkyl.

14 more elements

A compound selected from a compound of

(2R,5S)-7-Methyl-2-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5S)-7-Methyl-2-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5R)-7-Methyl-2-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5R)-7-methyl-2-[4-[4-(trifluoromethyl)-phenyl]-pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5R)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5R)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5R)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5R)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,6S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-1,8-diazaspiro[4.5]decan-7 one hydrochloride;
(2S,6S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-1,8-diazaspiro[4.5]decan-7-one hydrochloride;
(2R,5R)-2-[4-(5-Ethoxy-2-fluoro-phenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5R)-2-[4-(5-Ethoxy-2-fluoro-phenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5S)-7-Methyl-2-[4-[3-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6 one hydrochloride;
(2S,5S)-7-Methyl-2-[4-[3-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6 one hydrochloride;
(2S,5R)-7-Methyl-2-[4-[3-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6 one hydrochloride;
(2R,5R)-7-Methyl-2-[4-[3-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6 one hydrochloride;
(2S,5S)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethyl)-phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5R)-2-[4-(4-Isopropoxyphenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5R)-2-[4-(4-Isopropoxyphenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5R)-2-[4-(4-Isopropoxyphenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5S)-2-[4-(4-Isopropoxyphenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5S)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5S)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5R)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5R)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5S)-2-[4-[2-Fluoro-5-(trifluoromethoxy)phenyl]-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5S)-2-[4-[2-Fluoro-5-(trifluoromethoxy)phenyl]-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5R)-2-[4-[2-Fluoro-5-(trifluoromethoxy)phenyl]-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5R)-2-[4-[2-Fluoro-5-(trifluoromethoxy)phenyl]-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5S)-7-Methyl-2-[4-methyl-6-[3-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5S)-7-Methyl-2-[4-methyl-6-[3-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,6R)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-1,8-diazaspiro[4.5]decan-7-one hydrochloride;
(2S,6R)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-1,8-diazaspiro[4.5]decan-7-one hydrochloride;
(2R,5S)-2-[4-Methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5R)-2-[4-Methyl-6-[4-(trifluoromethyl)phenyl]-pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5S)-2-[4-Methyl-6-[4(trifluoromethyl)-phenyl]-pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5R)-2-[4-Methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5S)-8,8-Dimethyl-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5S)-8,8-Dimethyl-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5R)-8,8-Dimethyl-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
and
(2R,5R)-8,8-Dimethyl-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride
or free base preparation thereof.

44 more elements

A compound selected from a compound of

(2R,5S)-7-Methyl-2-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5S)-7-Methyl-2-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5R)-7-Methyl-2-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5R)-7-Methyl-2-[4-[4-(trifluoromethyl)-phenyl]-pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5R)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5R)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5R)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5R)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,6S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-1,8-diazaspiro[4.5]decan-7 one hydrochloride;
(2S,6S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-1,8-diazaspiro[4.5]decan-7-one hydrochloride;
(2R,5R)-2-[4-(5-Ethoxy-2-fluoro-phenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5R)-2-[4-(5-Ethoxy-2-fluoro-phenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5S)-7-Methyl-2-[4-[3-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5S)-7-Methyl-2-[4-[3-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2S,5R)-7-Methyl-2-[4-[3-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
(2R,5R)-7-Methyl-2-[4-[3-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride;
and
(2S,5S)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethyl)-phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one hydrochloride.

19 more elements

A compound selected from a compound of

(2R,5S)-7-Methyl-2-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one;
(2S,5S)-7-Methyl-2-[4-[4-(trifluoromethyl)phenyl] pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one;
(2S,5R)-7-Methyl-2-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1 ,7-diazaspiro[4.4]nonan-6-one;
(2R,5R)-7-Methyl-2-[4[4-(trifluoromethyl)-phenyl]-pyrimidin-2-yl]-1,7-diazaspiro [4.4]nonan -6- one;
(2S,5R)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one;
(2R,5R)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one;
(2S,5R)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro [4.4]nonan-6-one;
(2R,5R)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro [4.4]nonan-6-one;
2R,5S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one;
(2S,5S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-7-methyl- 1,7-diazaspiro[4.4]nonan-6-one;
(2R,6S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-1,8-diazaspiro[4.5]decan-7 one;
(2S,6S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-1 ,8-diazaspiro[4.5]decan-7-one;
(2R,5R)-2-[4-(5-Ethoxy-2-fluoro-phenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one;
(2S,5R)-2-[4-(5-Ethoxy-2-fluoro-phenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro [4.4]nonan-6-one;
(2S,5S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro [4.4]nonan-6-one;
(2R,5S)-2-[4-(5-Ethoxy-2-fluoro-phenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro [4. 4]nonan-6-one;
(2R,5S)-7-Methyl-2- [4- [3-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6 one;
(2S,5S)-7-Methyl-2- [4- [3-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6 one;
(2S,5R)-7-Methyl-2- [4-[3 -(trifluoromethoxy)phenyl]pyrimidin-2-yl-1,7-diazaspiro[4.4]nonan-6 one;
(2R,5R)-7-Methyl-2-[4-[3-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6 one;
(2S,5S)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethyl)-phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one;
(2R,5R)-2-[4-(4-Isopropoxyphenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one;
(2S,5R)-2-[4-(4-Isopropoxyphenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one;
(2S,5R)-2-[4-(4-Isopropoxyphenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one;
(2S,5S)-2-[4-(4-Isopropoxyphenyl)pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one;
(2R,5S)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one;
(2S,5S)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one;
(2S,5R)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl]- 1,7-diazaspiro[4.4]nonan-6-one;
(2R,5R)-7-Methyl-2-[4-methyl-6-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one;
(2S,5S)-2-[4-[2-Fluoro-5-(trifluoromethoxy)phenyl]-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro [4.4]nonan-6-one;
(2R,5S)-2-[4-[2-Fluoro-5-(trifluoromethoxy)phenyl]-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one;
(2R,5R)-2-[4-[2-Fluoro-5-(trifluoromethoxy)phenyl]-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro[4.4]nonan-6-one;
(2S,5R)-2-[4-[2-Fluoro-5-(trifluoromethoxy)phenyl]-6-methyl-pyrimidin-2-yl]-7-methyl-1,7-diazaspiro [4.4]nonan-6-one;
(2R,5S)-7-Methyl-2-[4-methyl-6-[3-(trifluoromethoxy)phenyl]pyrimidin-2-yl]- 1,7-diazaspiro [4.4]nonan-6-one;
(2S,5S)-7-Methyl-2-[4-methyl-6-[3-(trifluoromethoxy)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one;
(2R,6R)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-1,8-diazaspiro[4.5]decan-7-one;
(2S,6R)-2-[4-(5-Ethoxy-2-fluoro-phenyl)-6-methyl-pyrimidin-2-yl]-1,8-diazaspiro[4.5]decan-7-one;
(2R,5S)-2-[4-Methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one;
one;
(2S,5R)-2-[4-Methyl-6-[4-(trifluoromethyl)phenyl]-pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one;
(2S,5S)-2-[4-Methyl-6-[4(trifluoromethyl)-phenyl]-pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one;
(2R,5R)-2-[4-Methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro [4.4]nonan-6-one;
(2R,5S)-8,8-Dimethyl-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one;
(2S,5S)-8,8-Dimethyl-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one;
(2S,5R)-8,8-Dimethyl-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one;
and
(2R,5R)-8,8-Dimethyl-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one or a pharmaceutically acceptable salt thereof.

44 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/403,480Filed 22 May 2013 · us provisional application
Priority: GB 1209015.522 May 2012
Published: US 2015/0119404 A130 Apr 2015
Granted: 12 Apr 2016
Term ends: Not estimatedThe source records don’t support an estimate.

Classification33 codes

A61K 31/506
Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim: not condensed and containing further heterocyclic rings
A61K 31/407
Having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil: condensed with other…
A61K 31/438
Having six-membered rings with one nitrogen as the only ring hetero atom: the ring being spiro-condensed with carbocyclic or heterocyclic ring systems
A61P 3/12
Drugs for disorders of the metabolism: for electrolyte homeostasis

Family

Application61/650,325Us provisional application · filed 22 May 2012
Application61/773,710Us provisional application · filed 6 Mar 2013
US 2015/0119404 A1Pre-grant publication · published 30 Apr 2015
US 9,309,254 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

Facts

Application

14/403,480Filed 22 May 2013 · us provisional application

Priority

GB 1209015.522 May 2012

Published

US 2015/0119404 A130 Apr 2015

Granted

12 Apr 2016

Term ends

Not estimatedThe source records don’t support an estimate.

Classification33 codes

A61K 31/506
Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim: not condensed and containing further heterocyclic rings
A61K 31/407
Having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil: condensed with other…
A61K 31/438
Having six-membered rings with one nitrogen as the only ring hetero atom: the ring being spiro-condensed with carbocyclic or heterocyclic ring systems
A61P 3/12
Drugs for disorders of the metabolism: for electrolyte homeostasis