# US 9,751,824 B2 · Acetyl salicyclic acid dimers, synthesis thereof, and uses thereof to prevent and treat complement-mediated disorders

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 9,751,824 B2
- Document ID: US9751824B2
- Status: Granted
- Kind: B2
- Application number: 15/036,212
- Filed: 2014-11-17
- Published: 2016-10-13
- Granted: 2017-09-05
- Earliest claimed: 2013-11-18
- Assignees: Aurin Biotech Inc.
- Applicants: Aurin Biotech Inc.
- Inventors: Patrick L. McGeer; Moonhee Lee; Edith G. McGeer
- Web page: https://patentgrep.com/patent/US9751824B2

## CPC

- C07C 69/16: of dihydroxylic compounds
- A61K 8/375: {the alcohol moiety containing more than one hydroxy group}
- A61K 9/0014: {Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00)}
- A61P 7/00: Drugs for disorders of the blood or the extracellular fluid
- A61P 9/10: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A61P 13/02: of urine or of the urinary tract, e.g. urine acidifiers
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like
- A61P 17/04: Antipruritics
- A61P 17/08: Antiseborrheics
- A61P 17/10: Anti-acne agents
- A61P 17/14: for baldness or alopecia
- A61P 17/16: Emollients or protectives, e.g. against radiation
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 27/02: Ophthalmic agents
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 33/06: Antimalarials
- A61P 37/02: Immunomodulators
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A61Q 5/006: {Antidandruff preparations}
- A61Q 7/00: Preparations for affecting hair growth
- A61Q 19/004: {Aftersun preparations}
- A61Q 19/008: {Preparations for oily skin}
- C07C 69/017: Esters of hydroxy compounds having the esterified hydroxy group bound to a carbon atom of a six-membered aromatic ring
- 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
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

Dimers of acetyl salicylic acid, including 4,4′-diacetoxy-[1,1′-biphenyl]-3,3′-dicarboxylic acid (DAS-1) and 5,5′-methylenebis(2-acetoxybenzoic acid) (DAS-2) are provided. Methods of blocking the C3 convertase stage of the alternative complement pathway, preventing formation of the membrane attack complex of complement, and preventing or treating a complement-mediated disorder in a mammal including the step of administering dimers of acetyl salicylic acid are also provided.

## Claims

### Claim 1

A compound selected from the group consisting of
5,5′-methylenebis(2-acetoxybenzoic acid),
2-acetoxy-3-(4-acetoxy-3-carboxybenzyl)benzoic acid,
2-acetoxy-3-(3-acetoxy-4-carboxybenzyl)benzoic acid,
2-acetoxy-4-(4-acetoxy-3-carboxybenzyl)benzoic acid,
3,3′-methylenebis(2-acetoxybenzoic acid),
4,4′-methylenebis(2-acetoxybenzoic acid),
and salts thereof.

### Claim 2 (depends on 1)

A compound according to claim 1, which is 5,5′-methylenebis(2-acetoxybenzoic acid), or a salt thereof.

### Claim 3

A pharmaceutical composition comprising:
a. a compound selected from the group consisting of:
i. 5,5′-methylenebis(2-acetoxybenzoic acid),
ii. 2-acetoxy-3-(4-acetoxy-3-carboxybenzyl)benzoic acid,
iii. 2-acetoxy-3-(3-acetoxy-4-carboxybenzyl)benzoic acid,
iv. 2-acetoxy-4-(4-acetoxy-3-carboxybenzyl)benzoic acid,
v. 3,3′-methylenebis(2-acetoxybenzoic acid), and
vi. 4,4′-methylenebis(2-acetoxybenzoic acid); and
b. a pharmaceutically acceptable carrier.

### Claim 4 (depends on 3)

A method of treating a complement-mediated disorder in a mammal, the method comprising administering to the mammal a pharmaceutical composition according to claim 3, wherein the complement-mediated disorder is selected from the group consisting of paroxysmal nocturnal hemoglobinemia, age-related macular degeneration, Alzheimer's disease, rheumatoid arthritis, atherosclerosis, atypical hemolytic uremia syndrome, multiple sclerosis, malaria, inflammatory skin disorder, androgenetic alopecia, thermal or ultraviolet burn, acne, atopic dermatitis, dandruff/seborrheic dermatitis, pemphigus, erythematosus and cicatricial alopecia.