# US 8,569,466 B2 · Aromatic carboxylic acid derivatives for treatment and prophylaxis of gastrointestinal diseases including colon cancers

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- Number: US 8,569,466 B2
- Document ID: US8569466B2
- Status: Granted
- Kind: B2
- Application number: 13/063,445
- Filed: 2009-09-10
- Published: 2011-12-29
- Granted: 2013-10-29
- Earliest claimed: 2008-09-10
- Applicants: Nnochiri Ekwuribe
- Inventors: Nnochiri Ekwuribe
- Web page: https://patentgrep.com/patent/US8569466B2

## CPC

- A61K 31/655: Azo (—N=N—), diazo (=N2), azoxy (>N—O—N< or N(=O)—N<), azido (—N3) or diazoamino (—N=N—N<) compounds
- A01N 41/04: Sulfonic acids; Derivatives thereof
- A01N 41/06: Sulfonic acid amides
- A01N 41/08: Sulfonic acid halides; alpha-Hydroxy-sulfonic acids; Amino-sulfonic acids; Thiosulfonic acids; Derivatives thereof
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A61P 1/14: Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 31/04: Antibacterial agents
- A61P 31/10: Antimycotics
- A61P 31/12: Antivirals
- A61P 35/00: Antineoplastic agents
- A61P 37/02: Immunomodulators
- C07C 245/06: with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
- C07C 245/08: with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
- C07C 309/15: the nitrogen atom of at least one of the amino groups being part of any of the groups [IMAGE cpc-sch-C07C-0975.gif], X being a hetero atom, Y being any atom
- C07C 309/24: of a carbon skeleton containing six-membered aromatic rings
- C07C 311/46: Y being a hydrogen or a carbon atom
- C07C 311/49: to nitrogen atoms
- C07C 311/54: either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
- C07D 311/54: substituted in the carbocyclic ring
- C07D 311/68: with nitrogen atoms directly attached in position 4
- 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)
- A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Prodrug compounds which metabolize into 5-ASA or analogs thereof, and taurine or analogs thereof, in the colon site are disclosed. Pharmaceutical compositions including the compounds, and methods of treatment using the compounds, are also disclosed. Such compounds have utility for treating or preventing gastrointestinal disorders, including colon cancer, ulcerative colitis and Crohn's disease.

## Claims

### Claim 1

A compound of one of the formulas:
wherein:
R is selected from the group consisting of —OH, —HNCH2CH2SO3H, —HNCH2CH2SO2N3, —HNCH2CH2SO2NHR6, —HNCH2CO2H and —HNCH(CO2H)CH2COOH;
Z is selected from the group consisting of H, C1-6 alkyl (including cycloalkyl), alkenyl, heterocyclyl, aryl, heteroaryl, F, Cl, Br, I, —OR′, —NR′R″, —CF3, —CN, —NO2, —C2R′, —SR', —N3, —C(═O)NR′R″, —NR′C(═O)R″, —C(═O)R′, —C(═O)OR′, —OC(═O)R′, —OC(═O)NR′R″, —NR′C(═O)O R″, —SO2R′, —SO2NR′R″, and —NR′SO2R″,
R′ and R″ are individually hydrogen, C1-6 alkyl, cycloalkyl, heterocyclyl, aryl, or arylalkyl;
J is selected from the group consisting of —SO3H, SO2N3, SO2NHR6, and CO2H; and
R6 is H or C1-8 alkyl,
and pharmaceutically acceptable salts and esters thereof.

### Claim 2

A compound is presented by the formula:

### Claim 3 (depends on 1)

A pharmaceutical composition comprising a dose form including one of more of compounds of claim 1.

### Claim 4 (depends on 3)

The composition of claim 3, further comprising a co-active ingredient selected from among anti-inflammatory agents, immunomodulators, steroidal compounds and antibiotics.