# US 10,869,866 B2 · Benzathine analogs

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- Number: US 10,869,866 B2
- Document ID: US10869866B2
- Status: Granted
- Kind: B2
- Application number: 16/444,879
- Filed: 2019-06-18
- Published: 2020-04-16
- Granted: 2020-12-22
- Earliest claimed: 2012-06-08
- Assignees: University of Pittsburgh—Of the Commonwealth System of Higher Education; The United States Government as represented by the Department of Veterans Affairs
- Applicants: University of Pittsburgh—Of the Commonwealth System of Higher Education; The United States Government as represented by the Department of Veterans Affairs
- Inventors: Beibei Chen; Rama K. Mallampalli
- Web page: https://patentgrep.com/patent/US10869866B2

## CPC

- A61K 31/506: not condensed and containing further heterocyclic rings
- A61K 31/137: Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine {or methadone}
- A61K 31/341: not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
- A61K 31/381: having five-membered rings
- A61K 31/402: 1-aryl substituted, e.g. piretanide
- A61K 31/4155: non condensed and containing further heterocyclic rings
- A61K 31/4178: not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
- A61K 31/427: not condensed and containing further heterocyclic rings
- A61K 31/435: having six-membered rings with one nitrogen as the only ring hetero atom
- A61K 31/4418: having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
- A61K 31/444: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
- A61K 31/5375: 1,4-Oxazines, e.g. morpholine
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 11/06: Antiasthmatics
- A61P 19/00: Drugs for skeletal disorders
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 35/00: Antineoplastic agents
- C07C 211/01: having amino groups bound to acyclic carbon atoms
- C07C 211/53: having the nitrogen atom of at least one of the amino groups further bound to a hydrocarbon radical substituted by amino groups
- C07C 229/38: having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07D 207/06: with radicals, containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D 211/14: with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
- C07D 213/06: containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D 213/36: Radicals substituted by singly-bound nitrogen atoms (nitro radicals C07D213/26)
- C07D 213/38: having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
- C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 233/61: with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
- C07D 233/64: with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- C07D 239/26: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 265/30: not condensed with other rings
- C07D 277/28: Radicals substituted by nitrogen atoms
- C07D 295/135: with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 403/12: linked by a chain containing hetero atoms as chain links
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

A compound, or a pharmaceutically acceptable salt or ester thereof, having a structure of: wherein X is a divalent linking moiety; and R1-R10 are each individually H, optionally-substituted alkyl, optionally-substituted alkoxy, optionally-substituted aryl, optionally-substituted cycloalkyl, optionally-substituted heterocyclic, halogen, amino, or hydroxy, provided that at least one of R3 or R8 is an optionally-substituted alkyl, a substituted alkoxy, optionally-substituted aryl, optionally-substituted cycloalkyl, optionally-substituted heterocyclic, or halogen.

## Claims

### Claim 1

A compound, or a pharmaceutically acceptable salt or ester thereof, having a structure of formula II:
wherein X is an optionally-substituted aryldiyl; and
R1-R10 are each individually H, optionally-substituted alkyl, optionally-substituted alkoxy, optionally-substituted aryl, optionally-substituted cycloalkyl, optionally-substituted heterocycle, halogen, amino, or hydroxy, provided that at least one of R3 or R8 is an N-heterocycle selected from pyrrolyl, H-pyrrolyl, pyrrolinyl, pyrrolidinyl, oxazolyl, oxadiazolyl, isoxazolyl, furazanyl, thiazolyl, isothiazolyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, imidazolyl, imidazolinyl, triazolyl, tetrazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, or triazinyl.

### Claim 2 (depends on 1)

The compound of claim 1, wherein R3 is an N-heterocycle and R8 is an N-heterocycle.

### Claim 3 (depends on 1)

The compound of claim 1, wherein the N-heterocycle is selected from imidazolyl, pyridyl, pyrazolyl, oxadiazolyl, or pyrimidinyl.

### Claim 4 (depends on 1)

The compound of claim 1, wherein R1, R2, R4, R5, R6, R7, R9 and R10 are each H, and R3 and R8 are not H.

### Claim 5 (depends on 1)

A pharmaceutical composition comprising at least one compound of claim 1, and at least one pharmaceutically acceptable additive.

### Claim 6 (depends on 1)

The compound of claim 1, wherein X is phenylenediyl.

### Claim 7 (depends on 1)

The compound of claim 1, wherein the N-heterocycle is pyrazolidinyl.

### Claim 8 (depends on 1)

The compound of claim 1, wherein R3 and R8 are each pyrazolidinyl.

### Claim 9 (depends on 6)

The compound of claim 6, wherein R3 and R8 are each pyrazolidinyl.

### Claim 10 (depends on 1)

The compound of claim 1, wherein R1, R2, R4, R5, R6, R7, R9 and R10 are each H, and R3 and R8 are each pyrazolidinyl.

### Claim 11 (depends on 2)

The compound of claim 2, wherein X is phenylenediyl.

### Claim 12 (depends on 10)

The compound of claim 10, wherein X is phenylenediyl.