US 2019/0337902 A1Published application

Heterocyclic compounds as hiv protease inhibitors

AssigneeMerck Sharp & Dohme Corp.

InventorsTanweer Khan, Elizabeth Smith, Peter Williams, Catherine Wiscount, Brian McKittrick, John McCauley

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Abstract

The present invention is directed to compounds of Formula (I), pharmaceutical compositions comprising the same, and their use in the inhibition of HIV protease, the inhibition of HIV replication, the prophylaxis of infection by HIV, the treatment of infection by HIV, and the prophylaxis, treatment, and delay in the onset or progression of AIDS.

Claims14

Dependent claims

A compound of structural Formula I:

or a pharmaceutically acceptable salt thereof, wherein:
R1 is selected from hydrogen, halogen, C1-3alkyl, C1-3haloalkyl, —OC1-3haloalkyl, CN, —C(O)NHC1-6alkyl and —SO2C1-6alkyl;
R2 is selected from C6-10aryl, C1-6alkyl, (CH2)kC1-3haloalkyl, (CH2)kC3-6cycloalkyl, (CH2)kC6-10aryl, (CH2)kC5-10heterocycloalkyl and (CH2)kC5-10heteroaryl, wherein R2 is substituted with 0, 1, 2 or 3 of R6 selected from halogen, hydroxy, and C1-4alkoxy;
R3 is selected from hydrogen, C1-4alkyl, C3-8cycloalkyl C1-6alkyl, C3-8cycloalkyl, and C1-4haloalkyl, wherein R3 is substituted with 0, 1, 2 or 3 of R7 selected from halogen and hydroxy;
R4 is selected from C1-6alkyl carbonyl, C1-6alkylcarboxy, and C3-8alkylcycloalkylcarboxy, wherein R4 is substituted with 0, 1, 2, or 3 of R8 selected from C1-6alkyl and halogen;
R5 is selected from C3-8cycloalkyl C1-6alkyl, C3-8heterocycloalkyl C1-6alkyl, C6-10aryl C1-6alkyl, and C5-10heteroaryl C1-6alkyl, R5 is substituted with 0, 1, or 2 of R9 selected from C1-5alkyl, cyano, C1-6alkoxy, and halogen;
n is 1, 2, 3, 4, 5, or 6;
p is 0, 1, 2, or 3;
and
k is 0, 1, 2, 3, or 4.

7 more elements

The compound which is:

N-{4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}-N-alpha-(methoxycarbonyl)-O-methyl-L-tyrosinamide;
N-alpha-acetyl-N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-L-phenylalaninamide;
N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
2-amino-N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-4-phenylbutanamide;
N-alpha-(ethoxycarbonyl)-N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-L-phenylalaninamide;
N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)-1-methylbutyl]-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
methyl [2-{[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]amino}-2-oxo-1-(pyridin-3-ylmethyl)ethyl]carbamate;
N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-3-pyridin-3-yl-L-alaninamide;
N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-3-pyridin-4-yl-L-alaninamide;
N-{4-[4,4-bis(4-fluorophenyl)-2-imino-5-oxoimidazoliddin-1-yl]-1-methylbutyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
methyl [2-{[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]amino}-2-oxo-1-(pyridin-2-ylmethyl)ethyl]carbamate;
methyl [2-{[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]amino}-2-oxo-1-(pyridin-4-ylmethyl)ethyl]carbamate;
N-[5-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)pentyl]-L-phenylalaninamide;
N-[5-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)pentyl]-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-L-phenylalaninamide;
N-{4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{4-[2-imino-4-(3-methylbutyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-L-phenylalaninamide;
N-{4-[2-imino-4-(3-methylbutyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
methyl [2-{[5-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)pentyl]amino}-2-oxo-1-(pyridin-4-ylmethyl)ethyl]carbamate;
methyl [2-({4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}amino)-2-oxo-1-(pyridin-4-ylmethyl)ethyl]carbamate;
methyl [2-({4-[2-imino-4-(3-methylbutyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}amino)-2-oxo-1-(pyridin-4-ylmethyl)ethyl]carbamate;
N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-N-alpha-{[(1-methylcyclopropyl)oxy]carbonyl}-L-phenylalaninamide;
3-cyano-N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-L-phenylalaninamide;
4-fluoro-N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-N-alpha-[(1-methylethoxy)carbonyl]-L-phenylalaninamide;
4-fluoro-N-{4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{1-(cyclopropylmethyl)-4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
3-chloro-N-{1-(cyclopropylmethyl)-4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
2-chloro-N-{1-(cyclopropylmethyl)-4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
3-chloro-N-{1-cyclopropyl-4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
2-chloro-N-{1-cyclopropyl-4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
2-chloro-N-{4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
3-chloro-N-{4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{1-cyclopropyl-4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
4-chloro-N-{4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
methyl [2-({4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}amino)-1-(naphthalen-1-ylmethyl)-2-oxoethyl]carbamate;
N-{4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}-2-methoxy-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}-3-methoxy-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
methyl [1-(cyclohexylmethyl)-2-({4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}amino)-2-oxoethyl]carbamate;
methyl (1-((5-(2-imino-4-isobutyl-5-oxo-4-phenylimidazolidin-1-yl)pentan-2-yl)amino)-3-(naphthalen-2-yl)-1-oxopropan-2-yl)carbamate;
3-chloro-N-[4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-(1-methylethyl)butyl]-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
2-chloro-N-[4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-(1-methylethyl)butyl]-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-[4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-(1-methylethyl)butyl]-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-[4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-(trifluoromethyl)butyl]-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{1-ethyl-4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
4-chloro-N-{1-ethyl-4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
3-chloro-N-{1-ethyl-4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
2-chloro-N-{1-ethyl-4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{4-cyclopropyl-4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{5-cyclopropyl-4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]pentyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]pentyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]hexyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
and
N-{6-cyclopropyl-4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]hexyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
or a pharmaceutically acceptable salt thereof.

53 more elements

The compound which is:

N-{(1S)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}-N-alpha-(methoxycarbonyl)-O-methyl-L-tyrosinamide;
N-alpha-acetyl-N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-L-phenylalaninamide;
N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
(2S)-2-amino-N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-4-phenylbutanamide;
N-alpha-(ethoxycarbonyl)-N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-L-phenylalaninamide;
N-[(1S)-4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)-1-methylbutyl]-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
methyl [(1S)-2-{[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]amino}-2-oxo-1-(pyridin-3-ylmethyl)ethyl]carbamate;
N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-3-pyridin-3-yl-L-alaninamide;
N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-3-pyridin-4-yl-L-alaninamide;
N-{(1S)-4-[4,4-bis(4-fluorophenyl)-2-imino-5-oxoimidazolidin-1-yl]-1-methylbutyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
methyl [(1S)-2-{[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]amino}-2-oxo-1-(pyridin-2-ylmethyl)ethyl]carbamate;
methyl [(1S)-2-{[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]amino}-2-oxo-1-(pyridin-4-ylmethyl)ethyl]carbamate;
N-[5-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)pentyl]-L-phenylalaninamide;
N-[5-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)pentyl]-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-L-phenylalaninamide;
N-{4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{4-[2-imino-4-(3-methylbutyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-L-phenylalaninamide;
N-{4-[2-imino-4-(3-methylbutyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
methyl [(1S)-2-{[5-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)pentyl]amino}-2-oxo-1-(pyridin-4-ylmethyl)ethyl]carbamate;
methyl [(1S)-2-({4-[2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}amino)-2-oxo-1-(pyridin-4-ylmethyl)ethyl]carbamate;
methyl [(1S)-2-({4-[2-imino-4-(3-methylbutyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}amino)-2-oxo-1-(pyridin-4-ylmethyl)ethyl]carbamate;
N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-N-alpha-{[(1-methylcyclopropyl)oxy]carbonyl}-L-phenylalaninamide;
3-cyano-N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-L-phenylalaninamide;
4-fluoro-N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-[4-(2-imino-5-oxo-4,4-diphenylimidazolidin-1-yl)butyl]-N-alpha-[(1-methylethoxy)carbonyl]-L-phenylalaninamide;
4-fluoro-N-{(1S)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{(1S)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{1-(cyclopropylmethyl)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
3-chloro-N-{1-(cyclopropylmethyl)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
2-chloro-N-{1-(cyclopropylmethyl)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
3-chloro-N-{(1R)-1-cyclopropyl-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
2-chloro-N-{(1R)-1-cyclopropyl-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
2-chloro-N-{(1S)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
3-chloro-N-{(1S)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{(1R)-1-cyclopropyl-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
4-chloro-N-{(1S)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
methyl [(1S)-2-({(1S)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl)}amino)-1-(naphthalen-1-ylmethyl)-2-oxoethyl]carbamate;
N-{(1S)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}-2-methoxy-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{(1S)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}-3-methoxy-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
methyl [(1S)-1-(cyclohexylmethyl)-2-({(1S)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-methylbutyl}amino)-2-oxoethyl]carbamate;
methyl ((S)-1-(((S)-5-((R)-2-imino-4-isobutyl-5-oxo-4-phenylimidazolidin-1-yl)pentan-2-yl)amino)-3-(naphthalen-2-yl)-1-oxopropan-2-yl)carbamate;
3-chloro-N-[(1R)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-(1-methylethyl)butyl]-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
2-chloro-N-[(1R)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-(1-methylethyl)butyl]-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-[(1R)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-(1-methylethyl)butyl]-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-[(1R)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]-1-(trifluoromethyl)butyl]-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{(1S)-1-ethyl-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
4-chloro-N-{(1S)-1-ethyl-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
3-chloro-N-{(1S)-1-ethyl-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
2-chloro-N-{(1S)-1-ethyl-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{(4R)-4-cyclopropyl-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{(4S)-4-cyclopropyl-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]butyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{(4S)-5-cyclopropyl-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]pentyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{(4R)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]pentyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
N-{(4R)-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]hexyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
and
N-{(4R)-6-cyclopropyl-4-[(4R)-2-imino-4-(2-methylpropyl)-5-oxo-4-phenylimidazolidin-1-yl]hexyl}-N-alpha-(methoxycarbonyl)-L-phenylalaninamide;
or a pharmaceutically acceptable salt thereof.

54 more elements

Dependencies are inferred from the claim text.

Facts

Application: 16/466,783Filed 1 Dec 2017
Priority: 6 Dec 2016
Published: 7 Nov 2019
Term ends: Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07D 233/88
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
A61K 31/4168
1,3-Diazoles: having a nitrogen attached in position 2, e.g. clonidine
A61K 31/4439
Containing further heterocyclic ring systems: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links

Family

Application62/430,644Us provisional application · filed 6 Dec 2016
US 10,696,639 B2Related patent
US 2019/0337902 A1This patent

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

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Abstract

Facts

Application

16/466,783Filed 1 Dec 2017

Priority

6 Dec 2016

Published

7 Nov 2019

Term ends

Not estimatedThe source records don’t support an estimate.

Classification6 codes

C07D 233/88
With hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals,…:…
A61K 31/4168
1,3-Diazoles: having a nitrogen attached in position 2, e.g. clonidine
A61K 31/4439
Containing further heterocyclic ring systems: containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links