# US 8,569,335 B2 · Compounds derived from taurine, process of their preparation and pharmaceutical compositions containing these

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- Number: US 8,569,335 B2
- Document ID: US8569335B2
- Status: Granted
- Kind: B2
- Application number: 12/937,188
- Filed: 2009-04-09
- Published: 2011-05-19
- Granted: 2013-10-29
- Earliest claimed: 2008-04-09
- Assignees: Ems S.A.; Universidade Estadual Paulista Julio de Mesquinta Filho—UNESP
- Applicants: Ednir D. Vizioli; Chung M. Chin; Renato F. Menegon; Lorena Blau; Jean L. Santos; Maria D. Longo
- Inventors: Ednir D. Vizioli; Chung M. Chin; Renato F. Menegon; Lorena Blau; Jean L. Santos; Maria D. Longo
- Web page: https://patentgrep.com/patent/US8569335B2

## CPC

- A61K 31/404: Indoles, e.g. pindolol
- A61K 31/185: Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids (hydroxamic acids A61K31/16; peroxy acids A61K31/327)
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 1/04: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 303/22: from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; {from sulfonic halides by reactions not involving the formation of halosulfonyl groups}
- 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 317/44: having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07D 207/20: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 207/333: Radicals substituted by oxygen or sulfur atoms
- C07D 207/337: Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 209/12: Radicals substituted by oxygen atoms
- C07D 209/26: with an acyl radical attached to the ring nitrogen atom
- C07D 209/46: with an oxygen atom in position 1
- C07D 209/60: Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
- C07D 209/88: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D 213/30: Oxygen atoms
- C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 231/36: with hydrocarbon radicals, substituted by hetero atoms, attached in position 4
- C07D 231/56: Benzopyrazoles; Hydrogenated benzopyrazoles
- C07D 263/32: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D 263/57: Aryl or substituted aryl radicals
- C07D 277/24: Radicals substituted by oxygen atoms
- C07D 277/30: Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 333/22: Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
- C07D 333/24: Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D 471/04: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07D 491/04: Ortho-condensed systems
- C07D 495/04: Ortho-condensed systems
- C07C 2601/14: The ring being saturated
- C07C 2602/08: the other ring being five-membered, e.g. indane
- 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)

## Abstract

The present invention relates to compounds derived from taurine with non-steroidal anti inflammatory activity. In a first embodiment, the present invention relates to compounds derived from taurine, in which taurine is bound directly by means of an amide bond or through an spacing group, to a compound selected from the group of non-steroidal anti inflammatory compounds, cited as derived from taurine presenting the Formula (I): in which R means the component with non-steroidal anti inflammatory activity. In a second embodiment, the invention provides a process for obtaining the compounds of Formula (I) by reaction of taurine with a compound belonging to the group of non-steroidal anti inflammatory (NSAIs), in order to obtain a compound derived from taurine by direct bond or through a spacing group of the taurine to the NSAI. The invention also relates to the pharmaceutical compositions comprising at least one compound derived from taurine presenting non-steroidal anti inflammatory activity.

## Claims

### Claim 1

A taurine derivative compound of Formula (I)
and its salts, solvates, hydrates, enantiomers, diasteroisomers and polymorphs:
in which R is derived and selected from the group of compound consisting of:
2-[(2,6-dichloro-3-methylphenyl)amino]benzoic acid,
2-{[3-(trifluoromethyl)phenyl]amino}nicotinic acid,
2-[(2,3-dimethylphenyl)amino]benzoic acid,
[2-(2,4-dichlorophenoxy)phenyl]acetic acid,
2-[(3-chloro-2-methylphenyl)amino]benzoic acid,
2-[(1,2-diphenyl-hydrazine)carbonyl]hexanoic acid,
4-[(4-butyl-3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)methoxy]-4-oxobutanoic acid,
(1,3,4-triphenyl-1H-pyrazol-5-yl)acetic acid,
[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]acetic acid,
[(1-benzyl-1H-indazole-3-yl)oxy]acetic acid,
[2-(4-chlorophenyl)-1,3-thiazol-4-yl]acetic acid,
3-(4,5-diphenyl-1,3-oxazol-2-yl)propanoic acid,
2-amino-6-benzyl-4,5,6,7-tetrahydrothien[2,3-c]pyridine-3-carboxylic acid,
2-(2-hydroxybenzoylic)acid,
[2-(aminocarbonyl)phenoxy]acetic acid,
2,5-dihydroxybenzoic acid,
2-(acetyloxy)benzoic acid,
2-(sulphooxy)benzoic acid,
2-[(2-hydroxybenzoyl)oxy]benzoic acid,
2-[(2-phenylethyl)amino]benzoic acid,
5-[(2-phenyl-4,5-dihydro-3H-benzo[e]-1H-indole-2-(2-hydroxybenzoic acid),
2′,4′-difluoro-4-hydroxy-1,1′-diphenyl-3-carboxylic acid,
2-(3-phenoxyphenyl)propanoic acid,
chloro(3-chloro-4-cyclo-hexylphenyl)acetic acid,
4-(3-chloro-4-cyclo-hexylphenyl)-4-oxobutanic acid,
6-chloro-5-cyclo-hexylindan-1-carboxylic acid,
2-{4-[(2-methylprop-2-enyl)amino]phenyl}propanoic acid,
2-(5-benzoyithien-2-yl)propanoic acid,
5-benzoyl-2,3-dihydro-1H-pyrolizine-1-carboxylic acid,
2-[2-(4-fluorophenyl)-1,3-benzoxazol-5-yl]propanoic acid,
2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]propanoic acid,
2-(4-imidazo[1,2-a]pyridin-2-ylphenyl)propanoic acid,
2-[3-chloro-4-(2,5-dihydro-1H-pyrol-1-yl)phenyl]propanoic acid,
carboxylic acid,
(11-oxo-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetic acid,
[4-(allyloxy)-3-chlorophenyl]acetic acid,
2-[4-(1-oxo-1,3-dihydro-2H-isoindole-2-yl)phenyl]propanoic acid,
6-chloro-5-cyclo-hexylindane-1-carboxylic acid,
2-[4-(2,5-dihydrothien-2-yl carbonyl)phenyl]propanoic acid,
2-(benzoylthien-2-yl)propanoic acid,
[1-(4-chlorophenyl)-2,5-dimethyl-1H-pyrol-3-yl]acetic acid,
2-(5H-cromeno[2,3-b]pyridin-7-yl)propanoic acid,
4-(1,1′-diphenyl-4-yl)-4-oxobutanic acid,
[4-(4-chlorophenyl)-1,3-thiazol-5-yl]acetic acid,
2-(6-methoxy-2-naphthyl)propanoic acid,
[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-yl]acetic acid,
{5-methoxy-2-methyl-1-[(2E)-3-phenylprop-2-enoyl]-1H-indole-3-yl}acetic acid,
({[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-yl]acetyl}oxy)acetic acid,
(1,8-diethyl-1,3,4,9-tetrahydrofurane[3,4-b]indole-1-yl)acetic acid,
{(1E-5-fluoro-2-methyl-1-[4-(methylsulphonyl)benzylidene]-1H-inden-3-yl}acetic acid, and
2-(6-chloro-9H-carbazol-2-yl)propanoic acid.

### Claim 2 (depends on 1)

The compound according to claim 1, wherein the compound is selected from group consisting of:
2-{[(2,6-dichloro-3-methylpheny)aminobenzoil]amide}ethanesulfonic acid
2-{[3-(trifluoromethyl)phenyl]amino}nicotinoyl]amide}ethanesulfonic acid
2-{[(2,3-dimethylphenyl)amino]benzoyl]amide}ethanesulfonic acid
2-{[(2,4-dichlorophenoxy)phenyl]acetyl]amide}ethanesulfonic acid
2-{[(3-chloro-2-methylphenyl)amino]benzoyl]amide}ethanesulfonic acid
2-{[(1,2-diphenyl-hydrazino)carbonyl]hexanoyl]amide}ethanesulfonic acid
4-{[(4-butyl-3,5-dioxo-1,2-diphenylpyrazolidin-4-yl)methoxy]-4-oxobutanoyl]amide}ethanesulfonic acid
{[(1,3,4-triphenyl-1H-pyrazol-5-yl)acetyl]amide}ethanesulfonic acid
{[[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]acetyl]amide}ethanesulfonic acid
{[(1-benzyl-1H-indazol-3-yl)oxy]acetyl]amide}ethanesulfonic acid
{[[2-(4-chlorophenyl)-1,3-thiazol-4-yl]acetyl]amide}ethanesulfonic acid
3-{[(4,5-diphenyl-1,3-oxazol-2-yl)propanoyl]amide}ethanesulfonic acid
2-{[amino-6-benzyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-3-carboxylyl]amide}ethanesulfonic acid
{[[2-(aminocarbonyl)phenoxy]acetyl]amide}ethanesulfonic acid
[(2,5-dihydroxybenzoyl)amide]ethanesulfonic acid
{[2-(sulphooxy)benzoyl]amide}ethanesulfonic acid
2-{[(2-hydroxybenzoyl)oxy]benzoyl]amide}ethanesulfonic acid
2-{[(2-phenylethy)amino]benzoyl]amide}ethanesulfonic acid
5-{[(2-phenyl-4,5-dihydro-3H-benzo[e]-1H-indole-2-(2-hydroxybenzoyl)amide]}ethanesulfonic acid
[(2′,4′-difluoro-4-hydroxy-1,1′-diphenyl-3-carboxylyl)amide]ethanesulfonic acid
{2-(3-phenoxyphenyl)propanoyl}amide ethanesulfonic acid
[chloro (3-chloro-4-cyclo-hexylphenyl)acetyl]amide ethanesulfonic acid
[4-(3-chloro-4-cyclo-hexylphenyl)-4-oxobutanoyl]amide ethanesulfonic acid
(6-chloro-5-cyclo-hexylindane-1-carboxyl)amide ethanesulfonic acid
2-{4-[(2-methylprop-2-enil)amino]phenyl-propanoyl}amide ethanesulfonic acid
[2-(5-benzoylthien-2-yl)propanoyl]amide ethanesulfonic acid
(5-benzoyl-2,3-dihydro-1H-pyrolizine-1-carboxyl)amide ethanesulfonic acid
{2-[2-(4-fluorophenyl)-1,3-benzoxazol-5-yl]propanoyl}amide ethanesulfonic acid
{2-[2-(4-chlorophenyl)-1,3-benzoxazol-5-yl]propanoyl}amide ethanesulfonic acid
[2-(4-imidazo[1,2-a]pyridin-2-ylphenyl)propanoyl]amide ethanesulfonic acid
[2-(5-benzoylthien-2-yl)propanoyl]amide ethanesulfonic acid
{2-[3-chloro-4-(2,5-dihydro-1H-pyrol-1-yl)phenyl]propanoyl}amide ethanesulfonic acid
[(11-oxo-6,11-dihydrodibenzo[b,e]oxepin-2-yl)acetyl]amide ethanesulfonic acid
{[4-(allyloxy)-3-chlorophenyl]acetyl}amide ethanesulfonic acid
{2-[4-(1-oxo-1,3-dihydro-2H-isoindole-2-yl)phenyl]propanoyl}amide ethanesulfonic acid
{2-[4-(2,5-dihydrothien-2-ylcarbonyl)phenyl]propanoyl}amide ethanesulfonic acid
[2-(5-benzoylthien-2-yl)propanoyl]amide ethanesulfonic acid
2-{[(5H-chromene[2,3-b]pyridin-7-yl)propanoyl]amide}ethanesulfonic acid
4-{[(1,1′-biphenyl-4-yl)-4-oxobutanoyl]amide}ethanesulfonic acid
2-{[2-(6-methoxy-2-naphthyl)propanoyl]amide}ethanesulfonic acid
[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-yl]acetyl]amide}ethanesulfonic acid
{[(5-methoxy-2-methyl-1-[(2E)-3-phenylprop-2-enoyl]-1H-indole-3-yl)acetyl]amide}ethanesulfonic acid
{[(1,8-diethyl-1,3,4,9-tetrahydrofuran[3,4-b]indole-1-yl)acetyl]amide}ethanesulfonic acid
{[((1E)-5-fluoro-2-methyl-1-[4-(methylsulphonyl)benzylidene]-1H-inden-3-yl)acetyl]amide}ethanesulfonic acid
2-{[(6-chloro-9H-carbazol-2-yl)propanoyl]amide}ethanesulfonic acid.

### Claim 3 (depends on 1)

The compound according to claim 1, wherein the compound is selected from the group consisting of:
2-{[2-(6-methoxy-2-naphthyl)propanoyl]amide}ethanesulfonic acid; and
[1-(4-chlorobenzoyl)-5-metoxy-2-methyl-1H-indole-3-yl]acetyl]amide}ethanesulfonic acid.