US 11,634,387 B2Granted

Compounds useful for treating liver diseases

AssigneeAbionyx Pharma SA

InventorJean-Louis Henri Dasseux

Life of this patent

Estimating the term…

Abstract

This invention provides compounds, for example, of Formulae (A)-(H) and (J)-(AA) and pharmaceutically acceptable salts, solvates, esters, amides, and prodrugs thereof. The invention further provides pharmaceutical compositions comprising a compound of the invention, and a pharmaceutically acceptable carrier or vehicle. The compounds and compositions disclosed herein are useful for treating or preventing various diseases and conditions, for example liver disease such as liver fibrosis, fatty liver disease, non-alcoholic fatty liver disease (NAFLD) or non-alcoholic steatohepatitis (NASH), and kidney diseases such as acute kidney injury (AKI).

Claims20

Dependent claims

A compound of Formula (C):

or a pharmaceutically acceptable salt, solvate, ester, amide, or prodrug thereof, wherein:
R1 is phenyl, naphthyl, pyridyl, thienyl, furyl, quinolyl or benzothienyl, any of which is unsubstituted or substituted with C1-8 alkyl, C1-8 haloalkyl, C1-8 alkoxy, C1-8 haloalkoxy, C2-8 alkenyl, C2-8 alkynyl, halogen, C2-7 acyl, benzoyl, hydroxyl, nitro, amino, phenyl or pyridyl;
R2 is C2-8 alkyl, C1-8 haloalkyl, C2-8 alkenyl, C2-8 alkynyl, 3-7 membered cycloalkyl, C1-8 alkyl substituted with a 3-7 membered cycloalkyl, or C1-6 alkyl substituted with phenyl, naphthyl or pyridyl, any of which is unsubstituted or substituted with C1-8 alkyl, C1-8 haloalkyl, C1-8 alkoxy, C1-8 haloalkoxy, C2-8 alkenyl, C2-8 alkynyl, halogen, C2-7 acyl, benzoyl, hydroxyl, nitro, amino, phenyl or pyridyl;
A is oxygen, sulfur or NR9 in which R9 is hydrogen or C1-8 alkyl;
X is a C1-8 alkylene chain which is unsubstituted or substituted with C1-8 alkyl, C1-8 alkoxy or hydroxyl, and which has 0 or 1 double bonds;
Y is C(═O), C(═N—OR10), CH(OR11), CH═CH, C≡C, or C(═CH2) in which each of R10 and R11 is hydrogen or C1-8 alkyl;
each of R3, R4 and R5 is independently hydrogen, C1-8 alkyl, C1-8 haloalkyl, C1-8 alkoxy, C1-8 haloalkoxy, C2-8 alkenyl, C2-8 alkynyl, halogen, C2-7 acyl, benzoyl, hydroxyl, nitro, amino, phenyl, or pyridyl;
optionally wherein at least one of R3, R4, and R5 is not hydrogen;
B is CH or nitrogen;
Z is oxygen or sulfur;
each of R6 and R7 is independently hydrogen, C1-8 alkyl, or C1-8 haloalkyl;
RX is CH2OH, COH, COOCH2CONRX4RX5, SO3H,
each RX4 and RX5 is independently alkyl, aryl, or heteroaryl;
or alternatively, RX4 and RX5 together with the carbon atom to which RX4 and RX5 are attached form a heterocycle;
each RX6 and RX7 is independently H, C1-6 alkyl, C2-6 alkenyl, or C2-6 alkynyl;
and
n is 0, 1, 2, 3, or 4.

14 more elements

A compound selected from the group consisting of:

1-(4-(2-hydroxyethoxy)-3-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-one;
1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-one;
3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)-1-(4-(2-hydroxyethoxy)-3-methylphenyl)propan-1-one;
3-(2-(4-chloro-2-hydroxyphenyl)-5-isopropyloxazol-4-yl)-1-(4-(2-hydroxyethoxy)-3-methylphenyl)propan-1-one;
3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)propan-1-one;
1-(3-allyl-4-(2-hydroxyethoxy)phenyl)-3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)propan-1-one;
3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)-1-(4-((2-hydroxyethyl)thio)-3-methylphenyl)propan-1-one;
3-(2-(4-chloro-2-hydroxyphenyl)-5-isopropyloxazol-4-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)propan-1-one;
2-(4-(3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)prop-1-en-1-yl)-2-methylphenoxy)ethan-1-ol;
2-(4-(3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)prop-1-en-1-yl)-2-methylphenoxy)ethan-1-ol;
3-(4-hexyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)-1-(4-(2-hydroxyethoxy)-3-methylphenyl)propan-1-one;
3-(4-hexyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)propan-1-one;
2-(4-(3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)prop-1-en-1-yl)-2-methylphenoxy)-2-methylpropan-1-ol;
1-(4-(2-hydroxyethoxy)-2-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-one;
3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)-1-(4-(2-hydroxyethoxy)-2-methylphenyl)propan-1-one;
1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-2-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-one;
3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-2-methylphenyl)propan-1-one;
1-(4-(2-hydroxyethoxy)-3-propylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-one;
1-(3-allyl-4-(2-hydroxyethoxy)phenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-one;
2-(4-(4-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)but-1-en-2-yl)-2-methylphenoxy)ethan-1-ol;
2-(4-(4-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)but-1-en-2-yl)-2-methylphenoxy)-2-methylpropan-1-ol;
3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)-1-(4-(2-hydroxyethoxy)-3-methylphenyl)-2-methylpropan-1-one;
3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)-2-methylpropan-1-one;
1-(4-(2-hydroxyethoxy)-3-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)prop-2-en-1-one;
1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)prop-2-en-1-one;
1-(4-(3-hydroxypropoxy)-3-methylphenyl)-3-(4-isopropyl-2-(4-methoxyphenyl)thiazol-5-yl)propan-1-one;
3-(2-(3,5-difluorophenyl)-4-isopropylthiazol-5-yl)-1-(4-(2-hydroxyethoxy)-3-methylphenyl)propan-1-one;
3-(2-(3,5-difluorophenyl)-4-isopropylthiazol-5-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)propan-1-one;
1-(4-(2-hydroxyethoxy)-3-methylphenyl)-3-(4-isopropyl-2-(naphthalen-2-yl)thiazol-5-yl)propan-1-one;
1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)-3-(4-isopropyl-2-(naphthalen-2-yl)thiazol-5-yl)propan-1-one;
3-(2-(4-butylphenyl)-4-isopropylthiazol-5-yl)-1-(4-(2-hydroxyethoxy)-3-methylphenyl)propan-1-one;
3-(2-(4-butylphenyl)-4-isopropylthiazol-5-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)propan-1-one;
1-(3-chloro-4-(2-hydroxyethoxy)phenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-one;
1-(3-chloro-4-((1-hydroxy-2-methylpropan-2-yl)oxy)phenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-one;
1-(3-chloro-4-(2-hydroxyethoxy)phenyl)-3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)propan-1-one;
1-(3-chloro-4-((1-hydroxy-2-methylpropan-2-yl)oxy)phenyl)-3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)propan-1-one;
1-(4-(2-hydroxyethoxy)-3-methylphenyl)-3-(5-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-4-yl)propan-1-one;
1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)-3-(5-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-4-yl)propan-1-one;
3-(2-(2,4-dichlorophenyl)-5-isopropylthiazol-4-yl)-1-(4-(2-hydroxyethoxy)-3-methylphenyl)propan-1-one;
3-(2-(2,4-dichlorophenyl)-5-isopropylthiazol-4-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)propan-1-one;
1-(3-(2-hydroxyethoxy)-4-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-one;
1-(3-((1-hydroxy-2-methylpropan-2-yl)oxy)-4-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-one;
1-(4-((1-hydroxypropan-2-yl)oxy)-3-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-one;
1-(4-(2-hydroxyethoxy)-3-methylphenyl)-3-(4-methyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-one;
2-(4-(3-(4-hexyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)prop-1-en-1-yl)-2-methylphenoxy)-2-methylpropan-1-ol;
3-(4-hexyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)-1-(3-((1-hydroxy-2-methylpropan-2-yl)oxy)-4-methylphenyl)propan-1-one;
3-(4-ethyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)-1-(4-(2-hydroxyethoxy)-3-methylphenyl)propan-1-one;
3-(4-ethyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)propan-1-one;
1-(4-(2-hydroxyethoxy)-3-methylphenyl)-3-(4-isopropyl-2-(p-tolyl)thiazol-5-yl)propan-1-one;
1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)-3-(4-isopropyl-2-(p-tolyl)thiazol-5-yl)propan-1-one;
2-((3-(2-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)ethyl)-5-methylbenzo[d]isoxazol-6-yl)oxy)ethan-1-ol;
1-(4-(2-hydroxyethyl)-3-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-one;
1-(4-(2-hydroxyethoxy)-3-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-ol;
(R)-1-(4-(2-hydroxyethoxy)-3-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-ol;
1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-ol;
3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)-1-(4-(2-hydroxyethoxy)-3-methylphenyl)propan-1-ol;
5-chloro-2-(4-(3-hydroxy-3-(4-(2-hydroxyethoxy)-3-methylphenyl)propyl)-5-isopropyloxazol-2-yl)phenol;
3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)propan-1-ol;
1-(3-allyl-4-(2-hydroxyethoxy)phenyl)-3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)propan-1-ol;
3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)-1-(4-((2-hydroxyethyl)thio)-3-methylphenyl)propan-1-ol;
5-chloro-2-(4-(3-hydroxy-3-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)propyl)-5-isopropyloxazol-2-yl)phenol;
3-(4-hexyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)-1-(4-(2-hydroxyethoxy)-3-methylphenyl)propan-1-ol;
3-(4-hexyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)propan-1-ol;
1-(4-(2-hydroxyethoxy)-2-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-ol;
3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)-1-(4-(2-hydroxyethoxy)-2-methylphenyl)propan-1-ol;
1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-2-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-ol;
3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-2-methylphenyl)propan-1-ol;
1-(4-(2-hydroxyethoxy)-3-propylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-one;
1-(3-allyl-4-(2-hydroxyethoxy)phenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-ol;
3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)-1-(4-(2-hydroxyethoxy)-3-methylphenyl)-2-methylpropan-1-ol;
3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)-2-methylpropan-1-ol;
1-(4-(2-hydroxyethoxy)-3-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)prop-2-en-1-ol;
1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)prop-2-en-1-ol;
1-(4-(3-hydroxypropoxy)-3-methylphenyl)-3-(4-isopropyl-2-(4-methoxyphenyl)thiazol-5-yl)propan-1-ol;
3-(2-(3,5-difluorophenyl)-4-isopropylthiazol-5-yl)-1-(4-(2-hydroxyethoxy)-3-methylphenyl)propan-1-ol;
3-(2-(3,5-difluorophenyl)-4-isopropylthiazol-5-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)propan-1-ol;
1-(4-(2-hydroxyethoxy)-3-methylphenyl)-3-(4-isopropyl-2-(naphthalen-2-yl)thiazol-5-yl)propan-1-ol;
1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)-3-(4-isopropyl-2-(naphthalen-2-yl)thiazol-5-yl)propan-1-ol;
3-(2-(4-butylphenyl)-4-isopropylthiazol-5-yl)-1-(4-(2-hydroxyethoxy)-3-methylphenyl)propan-1-ol;
3-(2-(4-butylphenyl)-4-isopropylthiazol-5-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)propan-1-ol;
1-(3-chloro-4-(2-hydroxyethoxy)phenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-ol;
1-(3-chloro-4-((1-hydroxy-2-methylpropan-2-yl)oxy)phenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-ol;
1-(3-chloro-4-(2-hydroxyethoxy)phenyl)-3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)propan-1-ol;
1-(3-chloro-4-((1-hydroxy-2-methylpropan-2-yl)oxy)phenyl)-3-(2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl)propan-1-ol;
1-(4-(2-hydroxyethoxy)-3-methylphenyl)-3-(5-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-4-yl)propan-1-ol;
1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)-3-(5-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-4-yl)propan-1-ol;
3-(2-(2,4-dichlorophenyl)-5-isopropylthiazol-4-yl)-1-(4-(2-hydroxyethoxy)-3-methylphenyl)propan-1-ol;
3-(2-(2,4-dichlorophenyl)-5-isopropylthiazol-4-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)propan-1-ol;
1-(3-(2-hydroxyethoxy)-4-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-ol;
1-(3-((1-hydroxy-2-methylpropan-2-yl)oxy)-4-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-ol;
1-(4-((1-hydroxypropan-2-yl)oxy)-3-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-ol;
1-(4-(2-hydroxyethoxy)-3-methylphenyl)-3-(4-methyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-one;
3-(4-hexyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)-1-(3-((1-hydroxy-2-methylpropan-2-yl)oxy)-4-methylphenyl)propan-1-ol;
3-(4-ethyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)-1-(4-(2-hydroxyethoxy)-3-methylphenyl)propan-1-ol;
3-(4-ethyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)-1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)propan-1-ol;
1-(4-(2-hydroxyethoxy)-3-methylphenyl)-3-(4-isopropyl-2-(p-tolyl)thiazol-5-yl)propan-1-ol;
1-(4-((1-hydroxy-2-methylpropan-2-yl)oxy)-3-methylphenyl)-3-(4-isopropyl-2-(p-tolyl)thiazol-5-yl)propan-1-ol;
1-(4-(2-hydroxyethyl)-3-methylphenyl)-3-(4-isopropyl-2-(4-(trifluoromethyl)phenyl)thiazol-5-yl)propan-1-ol;
and
pharmaceutically acceptable salts, solvates, esters, amides, and prodrugs thereof.

97 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/219,058Filed 31 Mar 2021 · continuation in part
Priority: 26 Sep 2019
Published: US 2022/0363632 A117 Nov 2022
Granted: 25 Apr 2023
Term ends: Not estimatedThe source records don’t support an estimate.

Classification20 codes

C07C 323/19
Having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton: with…
A61P 3/06
Drugs for disorders of the metabolism: antihyperlipidemics
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics
A61P 13/12
Drugs for disorders of the urinary system: of the kidneys

Family

Application62/906,288Us provisional application · filed 26 Sep 2019
PCT/IB2020/000808Parent of this continuation-in-part · filed 25 Sep 2020
Application17/195,334Parent of this continuation-in-part · filed 8 Mar 2021
US 2022/0363632 A1Pre-grant publication · published 17 Nov 2022
US 2021/0300890 A1Published application
US 11,634,387 B2This patent

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

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Abstract

Facts

Application

17/219,058Filed 31 Mar 2021 · continuation in part

Priority

26 Sep 2019

Published

US 2022/0363632 A117 Nov 2022

Granted

25 Apr 2023

Term ends

Not estimatedThe source records don’t support an estimate.

Classification20 codes

C07C 323/19
Having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton: with…
A61P 3/06
Drugs for disorders of the metabolism: antihyperlipidemics
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics
A61P 13/12
Drugs for disorders of the urinary system: of the kidneys

Family

Application62/906,288Us provisional application · filed 26 Sep 2019

PCT/IB2020/000808Parent of this continuation-in-part · filed 25 Sep 2020

Application17/195,334Parent of this continuation-in-part · filed 8 Mar 2021

US 2022/0363632 A1Pre-grant publication · published 17 Nov 2022

US 2021/0300890 A1Published application

US 11,634,387 B2This patent

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