DK2385948T3 - Kondenserede thiazol- og oxazolpyrimidinoner - Google Patents

Kondenserede thiazol- og oxazolpyrimidinoner Download PDF

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DK2385948T3
DK2385948T3 DK10760108.0T DK10760108T DK2385948T3 DK 2385948 T3 DK2385948 T3 DK 2385948T3 DK 10760108 T DK10760108 T DK 10760108T DK 2385948 T3 DK2385948 T3 DK 2385948T3
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oxo
thia
tetrahydro
carbonyl
amino
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Sanjay Srivastava
Laxmikant Chhipa
Ramesh Chandra Gupta
Shailesh Deshpande
Anita Chaudhari
Anookh Mohanan
Chaitanya Dutt
Vijay Chauthaiwale
Murali Badanthadka
Prashant G Jamadarkhana
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Torrent Pharmaceuticals Ltd
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    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
    • C07D513/16—Peri-condensed systems

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Claims (11)

1. Forbindelse med formlen (I) ih
farmaceutisk acceptable salte deraf og stereoisomerer, tautomerer, hydrater og solvater deraf; hvor, når Y er NR4, O, S eller S02, m er 1 til 2, og når Y er C(R5)(R6), er m 1 til 4; n er 1 til 6; P er -OH, -OR7, -NH2, -NHR7, -NR7 R7', -NHS02R7, -NHCOR7, -NHOH eller -NHOR7; X er -OH, -OR7, -SR7, -SOR7, -S02R7, -NHR7 eller -NR7R7’; Z er S eller O; R er hydrogen, lineær eller forgrenet (Cl-C8)-alkyl, -(Cl-C8)-alkylaryl eller -(C1-C8)-alkylheteroaryl; RI og R2 uafhængigt er udvalgt ffa hydrogen, lineær eller forgrenet -(Cl-C8)-alkyl, -(C3-C7)-cycloalkyl, aryl, heteroaryl, -CH2-aryl og -CH2-heteroaryl, eller RI og R2 kan forenes for sammen at danne en 3-6-leddet monocyklisk eller 9-12-leddet bicyklisk ring; R sammen med enten RI eller R2 ffa det tilstødende carbonatom kan danne en 3-6-leddet monocyklisk eller 8-11-leddet bicyklisk heteroaryl- eller heterocyclylring; R3 og R3’ ved hver forekomst er uafhængigt udvalgt fra hydrogen, lineær eller forgrenet (Cl-C8)-alkyl, (Cl-C5)-alkoxy og halo; R3 og R3 ’ kan også være til stede i gem-di-halo-, gem-di-alkyl- eller spirocycoalkylarrangement; R4 er udvalgt fra gruppen bestående af hydrogen, lineær eller forgrenet (Cl-C8)-alkyl, (C3-C7)-cycloalkyl, aryl, heteroaryl, -(Cl-C8)-alkyl-aryl, -(Cl-C8)alkyl-heteroaryl, -(Cl-C2)alkyl-heterocyclyl, -C(0)R8, -C(0)0R8, -C(0)NR8R9, -C(S)NR8R9 og -S02R8, hvor aryl- og heteroarylradikaler eventuelt er substitueret med én eller flere substituenter udvalgt ffa gruppen bestående af -(Cl-C8)-alkyl, -(C3-C7)-cycloalkyl, heterocyclyl, aryl, heteroaryl, -OH, -alkoxy, halo, CN, -CF3, -OCF3, -O-aryl, -S02-(Cl-C8)-alkyl, -S02-aryl, -NH2, -NHR10, -NR10R10’, -NH-CO-(Cl-C8)-alkyl, -NH-S02-(Cl-C8)-alkyl, -NH-S02-aryl, -COOH, -C(0)NH-alkyl, -CONH-aryl, -CONH-heteroaryl, -C(0)0-(Cl-C8)-alkyl, -C(0)0-aryl, -S02NH-(Cl-C8)-alkyl, -S02NH-aryl og -S02NH- heteroaryl; R5 og R6 uafhængigt er udvalgt fra gruppen bestående af hydrogen, lineær eller forgrenet (Cl-C8)-alkyl, (C3-C7)-cycloalkyl, aryl, heteroaryl, fluor, -COOH, -CONH-(Cl- C8)-alkyl, -NHCO-(Cl-C8)-alkyl, -NHCO-aryl , -NHCO-heteroaryl, -NH-S02(Cl-C8)-alkyl, - NH-S02-aryl og - NH-S02-heteroaryl; R5 og R6 kan forenes for sammen at danne en 3-6-leddet carbocyklisk, heteroaryl- eller heterocyclylring; R7, R7’, RIO og R10’ uafhængigt er udvalgt fra lineær eller forgrenet (Cl-C8)-alkyl, (C3-C7)-cycloalkyl og -(Cl-C8)-alkylaryl; R7 og R7’ eller RIO og R10’ sammen med det nitrogenatom, hvortil de er bundet, kan danne en 5-6-leddet monocyklisk eller 8-14-leddet bicyklisk mættet og delvis mættet ring. Ringen kan indeholde 1 til 3 heteroatomer udvalgt fra N, S og O. Hvor den mættede og delvis mættede ring eventuelt kan være substitueret med én eller flere substituenter uafhængigt udvalgt fra gruppen bestående af -(Cl-C8)-alkyl, -(C3-C7)-cycloalkyl, heterocyclyl, aryl, heteroaryl, -OH, -alkoxy, halo, -CN, -CF3, -OCF3, -O-aryl, - S02-(Cl-C8)-alkyl, -S02-aryl, -NH2, -NHR10, -NR10R10’, -NH-CO-(Cl-C8)-alkyl, -NH-S02-(C1-C8)alkyl, -NH-S02-aryl, -COOH, -C(0)NH-alkyl, -CONH-aryl, -CONH- heteroaryl, -C(0)0-(C1-C8)alkyl, -C(0)0-aryl, -S02NH-(Cl-C8)-alkyl, -S02NH-aryl og - S02NH-heteroaryl; R8 er udvalgt fra gruppen bestående af lineær eller forgrenet (Cl-C8)-alkyl, (C3-C7)-cycloalkyl, -(Cl-C8)-alkyl-(C3-C7)-cycloalkyl, heterocyclyl, aryl, -(Cl-C8)-alkyl-aryl, -(Cl-C2)-alkyl-heterocyclyl, heteroaryl og -(C l-C8)-alkyl-heteroaryl, hvor aryl- og heteroarylradikaler eventuelt er substitueret med én eller flere substituenter fra lineær eller forgrenet (Cl-C8)-alkyl, (C3-C7)-cycloalkyl, -(Cl-C8)-alkyl-(C3-C7)-cycloalkyl, aryl, heteroaryl, heterocyclyl, -OH, alkoxy, halo, -CN, -CF3, -OCF3, -O-aryl, -S02-(Cl-C8)-alkyl, -S02-aryl, -NH2, -NHR10, -NR10R10’, -NH-CO-(Cl-C8)-alkyl, -NH-S02-(Cl-C8)-alkyl, -C(0)0H, -C(0)NH-(C1-C8)-alkyl, -CONH-aryl, -CONH-heteroaryl, -NHCONH-(Cl-C8)-alkyl, -NHCONH-aryl, -S02NH-(Cl-C8)-alkyl, -S02NH-aryl og S02NH-heteroaryl; R9 er hydrogen, lineær eller forgrenet (Cl-C8)-alkyl eller -(Cl-C8)-alkylaryl; R8 og R9 sammen med det nitrogenatom, hvortil de er bundet, kan danne en 5-6-leddet mættet ring.
2. Forbindelse ifølge krav 1, der er udvalgt fra gruppen bestående af: [(2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino]- eddikesyre; 3-(carboxymethyl-carbamoyl)-2-hydroxy-4-oxo-5,8-dihydro-4H,6H-9-thia-l,4a,7-triaza- fluoren-7-carboxylsyreethylester; [(2-hydroxy-7-methansulfonyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl)-amino] -eddikesyre; {[2-hydroxy-7-(3-methyl-butyryl)-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl] -amino } -eddikesyre; {[2-hydroxy-4-oxo-7-(propan-2-sulfonyl)-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl] -amino} -eddikesyre; l-[(2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino]- cyclopentancarboxylsyre; {[2-hydroxy-4-oxo-7-(toluene-4-sulfonyl)-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3 -carbonyl] -amino } -eddikesyre; [(2-hydroxy-4-oxo-7-phenylcarbamoyl-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl)-amino] -eddikesyre; [(7-cyclopropanecarbonyl-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl)-amino]-eddikesyre; [(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carbonyl)-amino] -eddikesyre; [(2-hydroxy-4-oxo-7,8-dihydro-4H,6H-cyclopenta[4,5]thiazol[3,2-a]pyrimidin-3-carbonyl)-amino] -eddikesyre; [(2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino]-eddikesyre, natriumsalt; [(7-tert-butyl-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino] -eddikesyre; 3-[(2-hydroxy-4-oxo-7,8-dihydro-4H,6H-cyclopenta[4,5]thiazol[3,2-a]pyrimidin-3-carbonyl)-amino] -propionsyre; 3-[(7-tert-Butyl-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino] -propionsyre; {[7-(4-fluor-benzoyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl] -amino} -eddikesyre; {[7-(5-chlor-thiophen-2-sulfonyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3 -carbonyl] -amino } -eddikesyre; {[2-hydroxy-4-oxo-7-(5-trifluormethyl-pyridin-2-yl)-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl]-amino}-eddikesyre; {[2-hydroxy-4-oxo-7-(4-trifluormethoxy-benzensulfonyl)-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7- triaza-fluoren-3-carbonyl]-amino }-eddikesyre; {[7-(2,2-dimethyl-propionyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3 -carbonyl] -amino} -eddikesyre; {[7-(4-butyl-benzoyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl] -amino } -eddikesyre; {[2-hydroxy-4-oxo-7-(4-trifluormethoxy-benzoyl)-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3 -carbonyl] -amino} -eddikesyre; {[7-(4-chlor-benzyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluoren-3-carbonyl] -amino } -eddikesyre; {[7-(4-fluor-phenylthiocarbamoyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl]-amino }-eddikesyre; [(2-hydroxy-7-isopropylthiocarbamoyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl)-amino]-eddikesyre; 3-(carboxymethyl-carbamoyl)-2-hydroxy-4-oxo-5,8-dihydro-4H,6H-9-thia-l,4a,7-triaza- fluoren-7-carboxylsyre-benzylester; {[7-(2-cyclopropyl-acetyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3 -carbonyl] -amino } -eddikesyre; ({7-[2-(4-chlor-phenyl)-acetyl]-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza- fluoren-3-carbonyl}-amino)-eddikesyre; {[7-(2-cyclopentyl-acetyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3 -carbonyl] -amino } -eddikesyre; 3-[(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carbonyl)-amino] -propionsyre; {[2-hydroxy-7-(4-metho xy-benzyl)-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1,4a,7-triaza-fluoren-3 -carbonyl] -amino } -eddikesyre; 2-[(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carbonyl)-amino] -propionsyre; {[7-(6-chlor-pyridine-3-carbonyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3 -carbonyl] -amino} -eddikesyre; [(2-hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino] -eddikesyre; {[7-(6-chlor-pyridazin-3-yl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3 -carbonyl] -amino} -eddikesyre; {[7-(3-cyan-pyridin-2-yl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren- 3 -carbonyl] -amino } -eddikesyre; {[7-(3-chlor-4-methoxy-benzoyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3 -carbonyl] -amino} -eddikesyre; [(2-hydroxy-4-oxo-5,6,7,8,9,10-hexahydro-4H-ll-thia-l,4a-diaza-cycloocta[a]inden-3-carbonyi)-amino] -eddikesyre; [(2-hydroxy-7-indan-5-ylmethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl)-amino] -eddikesyre; 2-[(2-hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino] -propionsyre; {[7-(3,5-dimethoxy-benzoyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3 -carbonyl] -amino } -eddikesyre; {[2-hydroxy-7-(4-methansulfonyl-benzoyl)-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3 -carbonyl] -amino } -eddikesyre; 2-[(2-hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino]-3-methyl-smørsyre (L-isomer); 2-[(2-hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino]-propionsyre (D-isomer); {[7-(3,5-dichlor-4-methoxy-benzoyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl]-amino }-eddikesyre; {[7-(3,5-bis-trifluormethyl-benzyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl]-amino }-eddikesyre; {[2-hydroxy-4-oxo-7-(4-propyl-benzoyl)-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl] -amino } -eddikesyre; {[7-(3,5-bis-trifluormethyl-benzoyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl]-amino }-eddikesyre; {[7-(3,4-dichlor-benzyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3 -carbonyl] -amino } -eddikesyre; [(2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl)-amino]-eddikesyre, hydrochloridsalt; {[2-hydroxy-7-(7-methoxy-6-methyl-indan-4-ylmethyl)-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-1 ,4a,7-triaza-fluoren-3-carbonyl]-amino} -eddikesyre; {[2-hydroxy-4-oxo-7-(4-trifluormethyl-benzyl)-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3 -carbonyl] -amino} -eddikesyre; [(7,7-diethyl-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)- amino] -eddikesyre; 2-[(2-hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3- carbonyl)-amino]-2-methyl-propionsyre; [(2-hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino]-phenyl-eddikesyre, L-isomer; [(7-benzoylamino-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino] -eddikesyre; [(2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-oxa-l,4a-diaza-fluoren-3-carbonyl)-amino]- eddikesyre; [(2-hydroxy-7-methyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino] -eddikesyre; [(2-hydroxy-4-oxo-7-propyl-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino] -eddikesyre; [(2-hydroxy-6,6-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino] -eddikesyre; [(2-hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-methyl-amino] -eddikesyre; l-[(2-hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3- carbonyl)-amino]-cyclohexancarboxylsyre; 1-(7,7-dimethyl-2-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-piperidin-4-carboxylsyre; [(2-hydroxy-4-oxo-7-phenyl-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino] -eddikesyre; [(2-hydroxy-4-oxo-5,8-dihydro-4H,6H-7-oxa-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino]- eddikesyre; [(2-hydroxy-5,7,7-trimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino] -eddikesyre; [(2-hydroxy-4,7,7-trioxo-5,6,7,8-tetrahydro-4H-71ambda*6*,9-dithia-l,4a-diaza-fluoren-3-carbonyl)-amino] -eddikesyre; [(2-methylsulfanyl-4-oxo-5,8-dihydro-4H,6H-7,9-dithia-l,4a-diaza-fluoren-3-carbonyl)-amino] -eddikesyre; [(5-ethoxy-2-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3- carbonyl)-amino]-eddikesyre-ethylester; N-[(2'-hydroxy-4'-oxo-6',9'-dihydro-4'H,7'H-spiro[cyclopropan-l,8'-pyrimido[2,l b][l,3]benzothiazol]-3'-yl)carbonyl]glycin; [(7-isopropyl-2-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl)-amino] -eddikesyre; 3-(carboxymethyl-carbamoyl)-2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza- fluoren-7-carboxylsyre; {[7-(3,5-dimethyl-pyrazol-l-yl)-2-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3 -carbonyl] -amino} -eddikesyre; 2- [(2-hydroxy-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino]-3-methyl-pentansyre (L-isomer); 3- (lH-indol-2-yl)-2-[(2-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3-carbonyl)-amino]-propionsyre (L-isomer); 3-(3H-imidazol-4-yl)-2-[(2-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3 -carbonyl)-amino] -propionsyre (L-isomer); 3-(4-hydroxy-phenyl)-2-[(2-methylsulfanyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia-l,4a-diaza-fluoren-3 -carbonyl)-amino] -propionsyre (L-isomer); [(2-hydroxy-4-oxo-7-pyridin-4-ylmethyl-5,6,7,8-tetrahydro-4H-9-thia-l,4a,7-triaza-fluoren-3-carbonyl)-amino] -eddikesyre; 2-methylsulfanyl-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carboxylsyre (2-oxo-2-pyrrolidin-1 -yl-ethyl)-amid; [(2-hydroxy-7,7-dimethyl-4-oxo-5,6,7,8-tetrahydro-4H-9-thia- l,4a-diaza-fluoren-3-carbonyl-amino]-eddikesyre, dinatriumsalt; [(2-ethoxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carbonyl)-amino] -eddikesyre; [(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carbonyl)-amino]-eddikesyre, dinatriumsalt; [(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carbonyl)-amino]-eddikesyre, argininsalt (2:1); [(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carbonyl)-amino]-eddikesyre, lysinsalt; [(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carbonyl)-amino]-eddikesyre, dikaliumsalt; [(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carbonyl)-amino]-eddikesyre, calciumsalt (2:1); [(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carbonyl)- amino]-eddikesyre, magnesiumsalt (2:1); [(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carbonyl)-amino]-eddikesyre, ammoniumsalt; [(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carbonyl)-amino] -eddikesyre, diethylaminsalt; [(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carbonyl)-amino]-eddikesyre, cholinsalt; [(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carbonyl)-amino] -eddikesyre, tromethaminsalt; [(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carbonyl)-amino]-eddikesyre, histidinsalt; 2-methylsulfanyl-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carboxylsyre carbamoylmethyl-amid; 2-methylsulfanyl-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carboxylsyre hydroxycarbamoylmethyl-amid; [(4-chlor-benzyl)-(2-methylsulfanyl-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carbonyl)-amino]-eddikesyre; 4-[cyclopentyl-(2-methylsulfanyl-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo [a] azulen-3-carbonyl)-amino]-smørsyre; 2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carboxylsyre (2-oxo-2-pyrrolidin-1 -yl-ethyl)-amid; 2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carboxylsyre cyclohexylcarbamoylmethyl-amid; 2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo[a]azulen-3-carboxylsyre (benzylcarbamoyl-methyl)-amid; 4-[cyclopentyl-(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-l,4a-diaza-benzo [a] azulen-3-carbonyl)-amino]-smørsyre; [benzyl-(2-hydroxy-4-oxo-6,7,8,9-tetrahydro-4H,5H-10-thia-1,4a-diaza-benzo[a]azulen-3-carbonyl)-amino]-eddikesyre og farmaceutisk acceptable salte deraf.
3. Farmaceutisk sammensætning, der omfatter en terapeutisk effektiv mængde af én eller flere forbindelser ifølge krav 1 sammen med et farmaceutisk acceptabelt adjuvans, en farmaceutisk acceptabel fortynder eller bærer.
4. Forbindelse ifølge krav 1 til anvendelse i behandlingen af anæmi.
5. Forbindelse ifølge krav 1 til anvendelse i behandlingen af anæmi hos ældre eller anæmi i forbindelse med tilstande som kroniske sygdomme, nyresvigt, cancer, infektion, dialyse, kirurgi og kemoterapi.
6. Forbindelse ifølge krav 1 til anvendelse i behandlingen af vævsskade forårsaget af renal iskæmi, cardiovaskulær iskæmi, cerebrovaskulær iskæmi, hepatisk iskæmi eller perifer vaskulær iskæmi.
7. Forbindelse ifølge krav 1 til anvendelse i behandlingen af vævsskade forårsaget af iskæmiske forstyrrelser, herunder akut nyrelæsion, myokardieinfarkt, apopleksi, hepatisk iskæmi-reperfusionslæsion og perifere vaskulære sygdomme.
8. Anvendelse af en forbindelse ifølge krav 1 til fremstillingen af et medikament til behandling af anæmi.
9. Anvendelse af en forbindelse ifølge krav 1 til fremstillingen af et medikament til behandling af anæmi hos ældre eller anæmi i forbindelse med tilstande som kroniske sygdomme, nyresvigt, cancer, infektion, dialyse, kirurgi og kemoterapi.
10. Anvendelse af en forbindelse ifølge krav 1 til fremstillingen af et medikament til forebyggelse eller behandling af vævsskade forårsaget af renal iskæmi, cardiovaskulær iskæmi, cerebrovaskulær iskæmi, hepatisk iskæmi eller perifer vaskulær iskæmi.
11. Anvendelse af en forbindelse ifølge krav 1 til fremstillingen af et medikament til forebyggelse eller behandling af vævsskade forårsaget af iskæmiske forstyrrelser, herunder akut nyrelæsion, myokardieinfarkt, apopleksi, hepatisk iskæmi-reperfusionslæsion og perifere vaskulære sygdomme.
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