# US 8,541,430 B2 · Fused thiazolo and oxazolo pyrimidinones

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- Number: US 8,541,430 B2
- Document ID: US8541430B2
- Status: Granted
- Kind: B2
- Application number: 12/877,704
- Filed: 2010-09-08
- Published: 2011-06-02
- Granted: 2013-09-24
- Earliest claimed: 2009-11-27
- Assignees: Torrent Pharmaceuticals Limited
- Applicants: Sanjay Srivastava; Laxmikant Chhipa; Ramesh Chandra Gupta; Shailesh Deshpande; Anita Chaudhari; Anookh Mohanan; Chaitanya Dutt; Vijay Chauthaiwale; Murali Badanthadka; Prashant G. Jamadarkhana
- Inventors: Sanjay Srivastava; Laxmikant Chhipa; Ramesh Chandra Gupta; Shailesh Deshpande; Anita Chaudhari; Anookh Mohanan; Chaitanya Dutt; Vijay Chauthaiwale; Murali Badanthadka; Prashant G. Jamadarkhana
- Web page: https://patentgrep.com/patent/US8541430B2

## CPC

- C07D 513/04: Ortho-condensed systems
- A61P 7/06: Antianaemics
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 13/12: of the kidneys
- A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P 35/00: Antineoplastic agents
- C07D 513/14: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to novel compounds, their pharmaceutically acceptable salts, and their isomers, stereoisomers, conformers, tautomers, polymorphs, hydrates and solvates. The present invention also encompasses pharmaceutically acceptable compositions of said compounds and process for preparing novel compounds. The invention further relates to the use of the above-mentioned compounds for the preparation of medicament for use as pharmaceuticals.

## Claims

### Claim 1

A Compound of formula (I)
their pharmaceutically acceptable salts and their isomers, stereoisomers, conformers, tautomers, polymorphs, hydrates, and solvates;
Wherein,
When Y is NR4, O, S or SO2, m is 1 to 2 and when Y is C(R5)(R6), m is 1 to 4;
n is 1 to 6;
P is —OH, —OR7, —NH2, —NHR7, —NR7R7′, —NHSO2R7, —NHCOR7, —NHOH or —NHOR7;
X is —OH, OR7, —SR7, —SOR7, —SO2R7, —NHR7 or —NR7R7′;
Z is S or O;
R is hydrogen, linear or branched (C1-C8)alkyl, —(C1-C8)alkylaryl or —(C1-C8)alkylheteroaryl;
R1 and R2 are independently selected from hydrogen, linear or branched —(C1-C8)alkyl, —(C3-C7) cycloalkyl, aryl, heteroaryl, —CH2-aryl and —CH2-heteroaryl, or
R1 and R2 may join together to form a 3-6 membered monocyclic or 9-12 membered bicyclic ring;
R together with either R1 or R2 of adjacent carbon atom may form a 3-6 membered monocyclic or 8-11 membered bicyclic heteroaryl or heterocyclyl ring;
R3 and R3′ at each occurance is independently selected from hydrogen, linear or branched (C1-C8)alkyl, (C1-C5) alkoxy and halo;
R3 and R3′ may also present in gem di-halo, gem di-alkyl or spirocycoalkyl arrangement;
R4 is selected from the group consisting of hydrogen, linear or branched (C1-C8) alkyl, (C3-C7) cycloalkyl, aryl, heteroaryl, —(C1-C8) alkyl-aryl, —(C1-C8)alkyl-heteroaryl, —(C1-C2)alkyl-heterocyclyl, —C(O)R8, —C(O)OR8, —C(O)NR8R9, —C(S)NR8R9 and —SO2R8, wherein aryl and heteroaryl radicals are optionally substituted with one or more substituent selected from the group consisting of —(C1-C8) alkyl, —(C3-C7) cycloalkyl, heterocyclyl, aryl, heteroaryl, —OH, -alkoxy, halo, CN, —CF3, —OCF3, —O-aryl, —SO2—(C1-C8)-alkyl, —SO2-aryl, —NH2, —NHR10, —NR10R10′, —NH—CO—(C1-C8) alkyl, —NH—SO2—(C1-C8)alkyl, —NH—SO2-aryl, —COOH, —C(O)NH-alkyl, —CONH-aryl, —CONH-heteroaryl, —C(O)O—(C1-C8)alkyl, —C(O)O -aryl, —SO2NH—(C1-C8)alkyl, —SO2NH-aryl and —SO2NH-heteroaryl;
R5 and R6 are independently selected from the group consisting of hydrogen, linear or branched (C1-C8)alkyl, (C3-C7) cycloalkyl, aryl, heteroaryl, fluoro, —COOH, —CONH—(C1-C8)alkyl, —NHCO—(C1-C8)alkyl, —NHCO-aryl, —NHCO-heteroaryl, —NH—SO2(C1-C8)alkyl, —NH—SO2-aryl and —NH—SO2-heteroaryl;
R5 and R6 may join together to form a 3-6 membered carbocyclic, heteroaryl or heterocyclyl ring;
R7, R7′, R10 and R10′ are independently selected from linear or branched (C1-C8)alkyl, (C3-C7) cycloalkyl and —(C1-C8)alkylaryl;
R7 and R7′ or R10 and R10′ together with nitrogen atom to which they are attached, may form 5-6 membered monocyclic or 8-14 membered bicyclic saturated and partially saturated ring; the ring may contain 1 to 3 heteroatom selected from N, S & O; wherein saturated and partially saturated ring may be optionally substituted with one or more substituent independently selected from the group consisting of —(C1-C8)alkyl, —(C3-C7) cycloalkyl, heterocyclyl, aryl, heteroaryl, —OH, -alkoxy, halo, —CN, —CF3, —OCF3, —O-aryl, —SO2—(C1-C8)-alkyl, —SO2-aryl, —NH2, —NHR10, —NR10R10′, —NH—CO—(C1-C8)alkyl, —NH—SO2—(C1-C8)alkyl, —NH—SO2-aryl, —COOH, —C(O)NH-alkyl, —CONH-aryl, —CONH-heteroaryl, —C(O)O —(C1-C8)alkyl, —C(O)O-aryl, —SO2NH—(C1-C8)alkyl, —SO2NH-aryl and —SO2NH-heteroaryl;
R8 is selected from the group consisting of linear or branched (C1-C8) alkyl, (C3-C7) cycloalkyl, —(C1-C8)alkyl-(C3-C7)cycloalkyl, heterocyclyl, aryl, —(C1-C8)alkyl-aryl, —(C1-C2)alkyl-heterocyclyl, heteroaryl and —(C1-C8)alkyl-heteroaryl, wherein aryl and heteroaryl radicals are optionally substituted with one or more substituent selected from linear or branched (C1-C8)alkyl, (C3-C7)cycloalkyl, —(C1-C8)alkyl-(C3-C7)cycloalkyl, aryl, heteroaryl, heterocyclyl, —OH, alkoxy, halo, —CN, —CF3, —OCF3, —O-aryl, —SO2—(C1-C8)alkyl, —SO2-aryl, —NH2, —NHR10, —NR10R10′, —NH—CO—(C1-C8)alkyl, —NH—SO2—(C1-C8)alkyl, —C(O)OH, —C(O)NH—(C1-C8)alkyl, —CONH-aryl, —CONH-heteroaryl, —NHCONH—(C1-C8)alkyl, —NHCONH-aryl, —SO2NH—(C1-C8)alkyl, —SO2NH-aryl and —SO2NH-heteroaryl;
R9 is hydrogen, linear or branched (C1-C8)alkyl or —(C1-C8)alkylaryl;
R8 and R9 together with nitrogen atom to which they are attached, may form 5-6 membered saturated ring.

### Claim 2 (depends on 1)

The compound as claimed in claim 1, which is selected from the group consisting of:
[(2-Hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid;
3-(Carboxymethyl-carbamoyl)-2-hydroxy-4-oxo-5,8-dihydro-4H,6H-9-thia-1,4a,7-triaza-fluorene-7-carboxylic acid ethyl ester;
[(2-Hydroxy-7-methanesulfonyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl)-amino]-acetic acid;
{[2-Hydroxy-7-(3-methyl-butyryl)-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[2-Hydroxy-4-oxo-7-(propane-2-sulfonyl)-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
1-[2-Hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-cyclopentanecarboxylic acid;
{[2-Hydroxy-4-oxo-7-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
[(2-Hydroxy-4-oxo-7-phenylcarbamoyl-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl)-amino]-acetic acid;
[(7-Cyclopropanecarbonyl-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl)-amino]-acetic acid;
[(2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-acetic acid;
[(2-Hydroxy-4-oxo-7,8-dihydro-4H,6H-cyclopenta[4,5]thiazolo[3,2-a]pyrimidine-3-carbonyl)-amino]-acetic acid;
[(2-Hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid, sodium salt;
[(7-tert-Butyl-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid;
3-[(2-Hydroxy-4-oxo-7,8-dihydro-4H,6H-cyclopenta[4,5]thiazolo[3,2-a]pyrimidine-3-carbonyl)-amino]-propionic acid;
3-[(7-tert-Butyl-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-propionic acid;
{[7-(4-Fluoro-benzoyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[7-(5-Chloro-thiophene-2-sulfonyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[2-Hydroxy-4-oxo-7-(5-trifluoromethyl-pyridin-2-yl)-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[2-Hydroxy-4-oxo-7-(4-trifluoromethoxy-benzenesulfonyl)-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[7-(2,2-Dimethyl-propionyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[7-(4-Butyl-benzoyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[2-Hydroxy-4-oxo-7-(4-trifluoromethoxy-benzoyl)-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[7-(4-Chloro-benzyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[7-(4-Fluoro-phenylthiocarbamoyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
[(2-Hydroxy-7-isopropylthiocarbamoyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl)-amino]-acetic acid;
3-(Carboxymethyl-carbamoyl)-2-hydroxy-4-oxo-5,8-dihydro-4H,6H-9-thia-1,4a,7-triaza-fluorene-7-carboxylic acid benzyl ester;
{[7-(2-Cyclopropyl-acetyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
({7-[2-(4-Chloro-phenyl)-acetyl]-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl }-amino)-acetic acid;
{[7-(2-Cyclopentyl-acetyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
3-[(2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-propionic acid;
{[2-Hydroxy-7-(4-methoxy-benzyl)-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
2-[(2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-propionic acid;
{[7-(6-Chloro-pyridine-3-carbonyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
[(2-Hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid;
{[7-(6-Chloro-pyridazin-3-yl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[7-(3-Cyano-pyridin-2-yl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[7-(3-Chloro-4-methoxy-benzoyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
[(2-Hydroxy-4-oxo-5,6,7,8,9,10-hexahydro-4H-11-thia-1,4a-diaza-cycloocta[a]indene-3-carbonyl)-amino]-acetic acid;
[(2-Hydroxy-7-indan-5-ylmethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl)-amino]-acetic acid;
2-[(2-Hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-propionic acid;
{[7-(3,5-Dimethoxy-benzoyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[2-Hydroxy-7-(4-methanesulfonyl-benzoyl)-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
2-[(2-Hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-3-methyl-butyric acid (L-isomer);
2-[(2-Hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-propionic acid (D-isomer);
{[7-(3,5-Dichloro-4-methoxy-benzoyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[7-(3,5-Bis-trifluoromethyl-benzyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[2-Hydroxy-4-oxo-7-(4-propyl-benzoyl)-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[7-(3,5-Bis-trifluoromethyl-benzoyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[7-(3,4-Dichloro-benzyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
[(2-Hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl)-amino]-acetic acid, hydrochloride salt;
{[2-Hydroxy-7-(7-methoxy-6-methyl-indan-4-ylmethyl)-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
{[2-Hydroxy-4-oxo-7-(4-trifluoromethyl-benzyl)-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl]-amino}-acetic acid;
[(7,7-Diethyl-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid;
2-[(2-Hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-2-methyl-propionic acid;
[(2-Hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-phenyl-acetic acid, L-isomer;
[(7-Benzoylamino-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid;
[(2-Hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-oxa-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid;
[(2-Hydroxy-7-methyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid;
[(2-Hydroxy-4-oxo-7-propyl-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid;
[(2-Hydroxy-6,6-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid;
[(2-Hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-methyl -amino]-acetic acid;
1-[(2-Hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-cyclohexanecarboxylic acid;
1-(7,7-Dimethyl-2-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-piperidine-4-carboxylic acid;
[(2-Hydroxy-4-oxo-7-phenyl-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid;
[(2-Hydroxy-4-oxo-5,8-dihydro-4H,6H-7-oxa-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid;
[(2-Hydroxy-5,7,7-trimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid;
[(2-Hydroxy-4,7,7-trioxo-5,6,7,8-tetrahydro-4H-7lambda*6*,9-dithia-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid;
[(2-Methylsulfanyl-4-oxo-5,8-dihydro-4H,6H-7,9-dithia-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid;
[(5-Ethoxy-2-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid ethyl ester;
N-[(2′-hydroxy-4′-oxo-6′,9′-dihydro-4′H,7′H-spiro[cyclopropane-1,8′-pyrimido[2,1-b][1,3]benzothiazol]-3′-yl)carbonyl]glycine;
[(7-Isopropyl-2-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl)-amino]-acetic acid;
3-(Carboxymethyl-carbamoyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-7-carboxylic acid;
{[7-(3,5-Dimethyl-pyrazol-1-yl)-2-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl]-amino}-acetic acid;
2-[(2-Hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-3-methyl-pentanoic acid (L-isomer);
3-(1H-Indo1-2-yl)-2-[(2-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-propionic acid (L-isomer);
3-(3H-Imidazol-4-yl)-2-[(2-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-propionic acid (L-isomer);
3-(4-Hydroxy-phenyl)-2-[(2-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-propionic acid (L-isomer);
[(2-Hydroxy-4-oxo-7-pyridin-4-ylmethyl-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluorene-3-carbonyl)-amino]-acetic acid;
2-Methylsulfanyl-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carboxylic acid (2-oxo-2-pyrrolidin-1-yl-ethyl)-amide;
[(2-Hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a-diaza-fluorene-3-carbonyl)-amino]-acetic acid, Disodium salt;
[(2-Ethoxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-acetic acid;
[(2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-acetic acid, Disodium salt;
[(2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-acetic acid, arginine salt (2:1);
[(2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-acetic acid, lysine salt;
[(2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-acetic acid, dipotassium salt;
[(2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-acetic acid, calcium salt (2:1);
[(2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-acetic acid, magnesium salt (2:1);
[(2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-acetic acid, ammonium salt;
[(2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-acetic acid, diethylamine salt;
[(2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-acetic acid, choline salt;
[(2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-acetic acid, tromethamine salt;
[(2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-acetic acid, histidine salt;
2-Methylsulfanyl-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carboxylic acid carbamoylmethyl-amide;
2-Methylsulfanyl-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carboxylic acid hydroxycarbamoylmethyl-amide;
[(4-Chloro-benzyl)-(2-methylsulfanyl-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-acetic acid;
4-[Cyclopentyl-(2-methylsulfanyl-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-butyric acid;
2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carboxylic acid (2-oxo-2-pyrrolidin-1-yl-ethyl)-amide;
2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carboxylic acid cyclohexylcarbamoylmethyl-amide;
2-Hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carboxylic acid (benzylcarbamoyl-methyl)-amide;
4-[Cyclopentyl-(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-butyric acid;
[Benzyl-(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulene-3-carbonyl)-amino]-acetic acid; and
pharmaceutically acceptable salts thereof.

### Claim 3 (depends on 1)

A pharmaceutical composition comprising a therapeutically effective amount of one or more compound of claim 1, in association with a pharmaceutically acceptable adjuvant, diluent or carrier.