US 2022/0144868 A1Published application

Chiral n-heterocyclic phosphorodiamidic acids (nhpas) and derivatives as novel bronsted acid catalysts

AssigneeBoard of Regents of the Nevada System of Higher Education, on behalf of the University of Nevada

InventorsJun Yong Kang, Hai Huang

Life of this patent

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Abstract

Provided herein are diaryl and arylalkyl phosphonates, useful as intermediates in, for example, the synthesis of leukocyte elastase inhibitors, potassium channel modulators, chemiluminescence materials, and flame retardants, and methods for making same. Also provided are N-heterocyclic phosphorodiamidic acids (NHPAs) useful in reactions such as, for example, in the preparation of diaryl and arylalkyl phosphonates. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Claims20

Dependent claims

A compound having a structure represented by a formula selected from:

wherein each occurrence of is a single covalent bond;
wherein each of R1a, R1b, R1a′, and R1b′, when present, is independently selected from hydrogen, C1-C4 alkyl, and Ar1;
wherein each occurrence of Ar1, when present, is independently selected from C6-C14 aryl and 4-10 membered heteroaryl, and is substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino;
or wherein each of R1a and R1b are optionally covalently bonded together and, together with the intermediate atoms, comprise a 5- to 6-membered cycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino;
or wherein each of R1a′ and R1b′, when present, are optionally covalently bonded together and, together with the intermediate atoms, comprise a 5- to 6-membered cycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino;
and
wherein each of R2, R3, R2′, and R3′, when present, are independently selected from —Si(R20a)(R20b)R20c, Ar2, and —C(R21a)(R21b)Ar2;
wherein each occurrence of R20a, R20b, and R20c, when present, is independently selected from C1-C4 alkyl and phenyl;
wherein each occurrence of R21a and R21b, when present, is independently selected from hydrogen and C1-C4 alkyl;
wherein each occurrence of Ar2, when present, is independently selected from C6-C14 aryl and 4-10 membered heteroaryl, and is substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and phenyl;
or wherein each occurrence of is a double covalent bond;
wherein each of R1a and R2 are optionally covalently bonded together and, together with the intermediate atoms, comprise a 5- or 6-membered heterocycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, Ar3, and —C(R22a)(R22b)Ar3;
wherein each occurrence of R22a and R22b, when present, is independently selected from hydrogen and C1-C4 alkyl;
wherein each occurrence of Ar3, when present, is independently selected from C6-C14 aryl and 4-10 membered heteroaryl, and is substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino;
wherein each of R1a′ and R2′, when present, are optionally covalently bonded together and, together with the intermediate atoms, comprise a 5- or 6-membered heterocycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, Ar3, and —C(R22a)(R22b)Ar3;
wherein each of R1b and R3 are optionally covalently bonded together and, together with the intermediate atoms, comprise a 5- or 6-membered heterocycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, Ar4, and —C(R23a)(R23b)Ar4;
wherein each occurrence of R23a and R23b, when present, is independently selected from hydrogen and C1-C4 alkyl;
wherein occurrence of Ar4, when present, is independently selected from C6-C14 aryl and 4-10 membered heteroaryl, and is substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino;
and
wherein each of R1b′ and R3′, when present, are optionally covalently bonded together and, together with the intermediate atoms, comprise a 5- or 6-membered heterocycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, Ar4, and —C(R23a)(R23b)Ar4;
wherein R4, when present, is selected from —OH and —NHR24;
wherein R24, when present, is an amine protecting group,
provided that when the compound has a structure represented by a formula:
wherein each of R1a and R1b are hydrogen and R2 and R3 are Ar2, then each occurrence of Ar2 is substituted with 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino,
or wherein each of R1a and R1b are hydrogen, R2 and R3 are independently —C(R21a)(R21b)Ar2, and Ar2 is unsubstituted C10 aryl, then each occurrence of R21a is not hydrogen,
or wherein each of R1a and R1b are optionally covalently bonded together and, together with the intermediate atoms, comprise an unsubstituted 6-membered cycloalkyl, R2 and R3 are independently —C(R21a)(R21b)Ar2, and Ar2 is unsubstituted C10 aryl, then each occurrence of R21a is not hydrogen,
or a salt thereof.

24 more elements

A compound having a structure represented by a formula:

wherein n is selected from 0 and 1;
wherein each of R101a and R101b is independently selected from hydrogen, halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino, provided that at least one of R101a and R101b is —OH, —SH, or C1-C4 alkylamino;
wherein each of R102a, R102b, and R102c is independently selected from hydrogen, halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino;
wherein R103 is selected from C4-C8 alkyl and Ar101, provided that when R103 is C4-C8 alkyl, then either
(a) at least one of R101a and R101b is —SH or C1-C4 alkylamino, or
(b) then R101b is —OH;
wherein Ar101, when present, is selected from C6-C10 aryl and C5-C6 heteroaryl, and is substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and phenyl;
wherein R104 is selected from C1-C4 alkoxy and phenyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino;
and
wherein R105 is C1-C4 alkyl,
provided that when n is 0, R101a is —OH, R103 is C6 aryl, R104 is ethoxy, and R105 is ethyl, then either:
(c) at least two of R101b, R102a, R102b, and R102c are not hydrogen,
(d) R103 is substituted with 2 or 3 groups, or
(e) at least one of R101b, R201a, R102b, and R102c is not hydrogen and R103 is substituted with 1, 2, or 3 groups, and
provided that when n is 0, R101b is —OH, and R103 is C6 aryl or C6 heteroaryl, then either:
(f) each of R102a and R102b is hydrogen, or
(g) one of R102a and R102b is hydrogen and R104 is not the same as —OR5,
or a pharmaceutically acceptable salt thereof.

15 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/583,159Filed 24 Jan 2022
Priority: 16 Jun 2017
Published: 12 May 2022
Term ends: Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07F 9/65848
Having one phosphorus atom as ring hetero atom: cyclic amide derivatives of acids of phosphorus, in which two nitrogen atoms belong to the ring
B01J 31/0264
Phosphorus containing compounds: phosphorus acid amides
C07F 9/3241
The acid moiety containing a substituent or a structure which is considered as characteristic: esters of arylalkanephosphinic acids
C07F 9/4056
The acid moiety containing a substituent or a structure which is considered as characteristic: esters of arylalkanephosphonic acids

Family

Application62/521,086Us provisional application · filed 16 Jun 2017
Application62/566,834Us provisional application · filed 2 Oct 2017
Application62/568,645Us provisional application · filed 5 Oct 2017
Application16/622,451Continuation · filed 13 Dec 2019
Application17/583,159Continuation
US 11,248,014 B2Related patent
US 11,873,315 B2Related patent
US 2021/0147457 A1Published application
US 2022/0144868 A1This patent

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

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Abstract

A compound having a structure represented by a formula selected from:

wherein each occurrence of is a single covalent bond;
wherein each of R1a, R1b, R1a′, and R1b′, when present, is independently selected from hydrogen, C1-C4 alkyl, and Ar1;
wherein each occurrence of Ar1, when present, is independently selected from C6-C14 aryl and 4-10 membered heteroaryl, and is substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino;
or wherein each of R1a and R1b are optionally covalently bonded together and, together with the intermediate atoms, comprise a 5- to 6-membered cycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino;
or wherein each of R1a′ and R1b′, when present, are optionally covalently bonded together and, together with the intermediate atoms, comprise a 5- to 6-membered cycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino;
and
wherein each of R2, R3, R2′, and R3′, when present, are independently selected from —Si(R20a)(R20b)R20c, Ar2, and —C(R21a)(R21b)Ar2;
wherein each occurrence of R20a, R20b, and R20c, when present, is independently selected from C1-C4 alkyl and phenyl;
wherein each occurrence of R21a and R21b, when present, is independently selected from hydrogen and C1-C4 alkyl;
wherein each occurrence of Ar2, when present, is independently selected from C6-C14 aryl and 4-10 membered heteroaryl, and is substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, and phenyl;
or wherein each occurrence of is a double covalent bond;
wherein each of R1a and R2 are optionally covalently bonded together and, together with the intermediate atoms, comprise a 5- or 6-membered heterocycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, Ar3, and —C(R22a)(R22b)Ar3;
wherein each occurrence of R22a and R22b, when present, is independently selected from hydrogen and C1-C4 alkyl;
wherein each occurrence of Ar3, when present, is independently selected from C6-C14 aryl and 4-10 membered heteroaryl, and is substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino;
wherein each of R1a′ and R2′, when present, are optionally covalently bonded together and, together with the intermediate atoms, comprise a 5- or 6-membered heterocycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, Ar3, and —C(R22a)(R22b)Ar3;
wherein each of R1b and R3 are optionally covalently bonded together and, together with the intermediate atoms, comprise a 5- or 6-membered heterocycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, Ar4, and —C(R23a)(R23b)Ar4;
wherein each occurrence of R23a and R23b, when present, is independently selected from hydrogen and C1-C4 alkyl;
wherein occurrence of Ar4, when present, is independently selected from C6-C14 aryl and 4-10 membered heteroaryl, and is substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino;
and
wherein each of R1b′ and R3′, when present, are optionally covalently bonded together and, together with the intermediate atoms, comprise a 5- or 6-membered heterocycloalkyl substituted with 0, 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, (C1-C4)(C1-C4) dialkylamino, Ar4, and —C(R23a)(R23b)Ar4;
wherein R4, when present, is selected from —OH and —NHR24;
wherein R24, when present, is an amine protecting group,
provided that when the compound has a structure represented by a formula:
wherein each of R1a and R1b are hydrogen and R2 and R3 are Ar2, then each occurrence of Ar2 is substituted with 1, 2, or 3 groups independently selected from halogen, —NO2, —CN, —OH, —SH, —NH2, C1-C4 haloalkyl, C1-C4 cyanoalkyl, C1-C4 hydroxyalkyl, C1-C4 haloalkoxy, C1-C4 thioalkyl, C1-C4 alkylthiol, C1-C4 aminoalkyl, C1-C4 alkylamino, and (C1-C4)(C1-C4) dialkylamino,
or wherein each of R1a and R1b are hydrogen, R2 and R3 are independently —C(R21a)(R21b)Ar2, and Ar2 is unsubstituted C10 aryl, then each occurrence of R21a is not hydrogen,
or wherein each of R1a and R1b are optionally covalently bonded together and, together with the intermediate atoms, comprise an unsubstituted 6-membered cycloalkyl, R2 and R3 are independently —C(R21a)(R21b)Ar2, and Ar2 is unsubstituted C10 aryl, then each occurrence of R21a is not hydrogen,
or a salt thereof.

24 more elements

Facts

Application

17/583,159Filed 24 Jan 2022

Priority

16 Jun 2017

Published

12 May 2022

Term ends

Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07F 9/65848
Having one phosphorus atom as ring hetero atom: cyclic amide derivatives of acids of phosphorus, in which two nitrogen atoms belong to the ring
B01J 31/0264
Phosphorus containing compounds: phosphorus acid amides
C07F 9/3241
The acid moiety containing a substituent or a structure which is considered as characteristic: esters of arylalkanephosphinic acids
C07F 9/4056
The acid moiety containing a substituent or a structure which is considered as characteristic: esters of arylalkanephosphonic acids

Family

Application62/521,086Us provisional application · filed 16 Jun 2017

Application62/566,834Us provisional application · filed 2 Oct 2017

Application62/568,645Us provisional application · filed 5 Oct 2017

Application16/622,451Continuation · filed 13 Dec 2019

Application17/583,159Continuation

US 11,248,014 B2Related patent

US 11,873,315 B2Related patent

US 2021/0147457 A1Published application

US 2022/0144868 A1This patent

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