DK2897939T3 - Benzoimidazolcarboxylsyreamidderivater til behandling af metaboliske eller kardiovaskulære sygdomme - Google Patents
Benzoimidazolcarboxylsyreamidderivater til behandling af metaboliske eller kardiovaskulære sygdomme Download PDFInfo
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- DK2897939T3 DK2897939T3 DK13763087.7T DK13763087T DK2897939T3 DK 2897939 T3 DK2897939 T3 DK 2897939T3 DK 13763087 T DK13763087 T DK 13763087T DK 2897939 T3 DK2897939 T3 DK 2897939T3
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Claims (15)
1. Forbindelse
med formel I, hvor R', R", R'" uafhængigt af hinanden er H, halogen, CF3, OCF3, 0-(C1-C3) -alkyl; R1 er a) (C4-C7) -alkyl ; b) (C5-C7) -cycloalkyl, der er usubstitueret eller monosubstitueret med (C1-C2) -alkyl eller CF3; c) methylencyclohexyl; d) phenyl, der er usubstitueret eller monosubstitueret med methyl eller Cl; R2 er a) en 5-leddet heteroaryl, der indeholder 1 eller 2 identiske eller forskellige ringheteroatomer udvalgt blandt N, 0 og S, hvor den 5-leddede heteroaryl er usubstitueret eller monosubstitueret med Cl eller (C1-C4)-alkyl; b) phenyl; c) (C5-C6)-cycloalkyl; eller d) tetrahydrofuranyl; R3 er H eller (C1-C2) -alkyl; og R4 er a) (C3-C5)-alkyl, der eventuelt kan være substitueret med 1-3 F eller S-(C1-C4) -alkyl, b) (C0-C1)-alkylen-(C3-C7)-cycloalkyl, hvor cycloalkyl er usubstitueret eller mono- eller disubstitueret med methyl; c) (C0-C2) -alkylenphenyl, hvor phenyl er usubstitueret eller mono- eller disubstitueret med F, Cl, (C1-C4) -alkyl eller CF3; eller d) thienyl; eller R3 og R4 sammen med carbonatomet, hvortil de er bundet, danner en 5- til 7-leddet cycloalkylring, der er usubstitueret eller monosubstitueret med (C1-C4)-alkyl; R5 er H, (C1-C4) -alkyl eller OH; R6 er H eller (C1-C4)-alkyl; n er 0, 1 eller 2; og Z er CO2-R7, OR8, C (O) NR9R10, S (O) 2NRnR12,
·>: hvor v er 0 eller 2; R7 er H eller (C1-C4) -alkyl; R8 er H eller (C1-C4) -alkyl; R9 er H, (Ci-C4)-alkyl eller ethylen-O- (C1-C4) -alkyl; og R10 er a) H; b) (Ci-Ce) -alkyl, der er usubstitueret eller monosubstitueret med CF3; c) (C1-C2) -alkyl, der er substitueret med CN eller CO2R19,· hvor R19 er H eller (C1-C6)-alkyl; d) (C2-C4)-alkyl, der er monosubstitueret med en substituent udvalgt fra gruppen, der består af S-methyl, SO2NR20R21, O-R22 og NR23R24; hvor R20 er H; R21 er H; R22 er H, (C1-C3) -alkyl, methylencyclopropyl, methylenphenyl eller methylen-2-tetrahydrofuran; R23 er H eller (C1-C2)-alkyl; R24 er (C1-C2) -alkyl eller S02-methyl; e) (C3-C5)-cycloalkyl, der er usubstitueret eller monosubstitueret med phenyl; f) (C0-C2)-alkylenheterocycloalkyl, hvor heterocylcoalkyl er 5- eller 6-leddet og indeholder 1 eller 2 O-atomer i ikke-tilstødende positioner, og hvor heterocycloalkyl er usubstitueret eller geminalt disubstitueret med en spirocyclopentylring eller en spirocyclohexylring; g) (C2-C5)-alkylenheterocycloalkyl, hvor heterocycloalkyl er en 5-, 6- eller 7-leddet ring, der indeholder mindst ét N-atom, er bundet via N-atomet og yderligere kan indeholde ét heteroatom udvalgt fra gruppen, der består af 0, S(0)x eller NR25, i en position, der ikke støder op til N-atomet, hvormed ringen er bundet til alkylen, og hvor et hvilket som helst carbonatom i heterocycloalkyl er usubstitueret eller substitueret med 1 eller 2 substituenter udvalgt fra gruppen, der består af (C1-C3)alkyl eller methylenphenyl; hvor x er 2 ; R25 er H, (C1-C2) -alkyl, methylenphenyl eller phenyl, der er usubstitueret eller substitueret med 1 eller 2 substituenter udvalgt fra gruppen, der består af F, Cl og 0- (C1-C4)-alkyl; h) (C0-C3)-alkylenheterocycloalkyl, hvor heterocycloalkyl er en 5- eller 6-leddet ring, der indeholder mindst ét N-atom, ikke er bundet via N-atomet og yderligere kan indeholdet ét O-atom i en position, der ikke støder op til N-atomet, og hvor N-atomet er usubstitueret eller substitueret med en substituent udvalgt fra gruppen, der består af: i) (C1-C4)-alkyl, der er usubstitueret eller monosubstitueret med 0 (C1-C4)-alkyl; ii) methylencyclohexyl; iii) (C0-C2)-alkylenphenyl, hvor phenyl er usubstitueret eller substitueret med 1 eller 2 substituenter udvalgt fra gruppen, der består af F og 0(C1-C4)-alkyl; iv) (C0-C1) -alkylenpyridyl; v) pyrimidinyl; i) 8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl; j) 9-methyl-9-aza-bicyclo[3.3.1]non-3-yl; k) methylen-4-(octahydroquinolizinyl) ; l) (Co-C2)-alkylenphenyl, hvor phenyl er usubstitueret eller monosubstitueret med substituenter udvalgt fra gruppen, der består af F, O (C1-C4) -alkyl, N ( (C1-C4)-alkyl) 2, 4-morpholinyl og methylen-(4-methylpiperidin)-1-yl eller disubstitueret på tilstødende positioner med gruppen -0(CH2)0-; m) (C1-C2) -alkylenheteroaryl, hvor heteroarylringen er en 5- eller 6-leddet ring, der indeholder 1, 2, 3 eller 4 heteroatomer udvalgt blandt 0, S eller N; og hvor heteroarylringen er usubstitueret eller monosubstitueret med oxo (=0); eller R9 og R10 sammen med N-atomet, der bærer dem, er a) en 4-, 5- eller 6-leddet heterocylcoalkylring, der kun indeholder N-atomet, hvortil Rs og R10 er bundet, der er usubstitueret eller monosubstitueret med en substituent udvalgt fra gruppen, der består af: i) (C0-C1) -alkylen-OR26, hvor R26 er H, (C1-C3) -alkyl eller methylenphenyl ; ii) CO2R27, hvor R27 er H eller (C1-C6) -alkyl; ii) NR28R29, hvor R28 er (C1-C2) -alkyl, og R29 er (C1-C2) -alkyl, methylenphenyl eller ethylen-N((C1-C4)-alkyl)2; iii) 1-piperidinyl, der er usubstitueret eller monosubstitueret med methyl; iv) 1-piperazinyl, der er usubstitueret eller monosubstitueret med methyl; v) 4-morpholinyl; vi) 1-azepanyl; vii) 2- (2,3-dihydro-lH-isoindolyl); b) en 6- eller 7-leddet heterocycloalkylring, der indeholder N-atomet, hvortil R9 og R10 er bundet, og ét yderligere heteroatom udvalgt blandt 0, S eller NR30 i en position, der ikke støder op til N-atomet, hvortil R9 og R10 er bundet, hvor carbonatomerne i heterocycloalkylringen er usubstitueret eller mono- eller disubstitueret med methyl, og hvor R30 er i) H; ii) (C1-C4) -alkyl; iii) (C5-C6) -cycloalkyl; iv) phenyl, der er usubstitueret eller monosubstitueret med F, CF3 eller O- (C1-C4) -alkyl; v) methylenphenyl, der er usubstitueret eller mono- eller disubstitueret med F eller Cl eller disubstitueret på tilstødende positioner med gruppen -0(CH2)0-; vi) pyridyl; c) en 2,5-diaza-bicyclo[2.2.1]heptylring, der er usubstitueret eller substitueret på det andet N-atom i 5-position med en substituent udvalgt fra gruppen, der består af (C1-C4)-alkyl, methylencyclopentyl, phenyl, der er usubstitueret eller monosubstitueret med F, methylenphenyl, hvor phenyl er usubstitueret eller monosubstitueret med 0- (C1-C4) -alkyl eller cf3; R11 er H; R12 er (C1-C4) -alkyl; R13 er H; R14 er CF3 eller methylen-O- (C1-C4) -alkyl; R15 er cyclopropyl eller phenyl; R16 er H eller (C1-C4) -alkyl; R17 er H eller (C1-C4) -alkyl; og R18 er (C1-C4) -alkyl; i en hvilken som helst af dens stereoisomere former eller en blanding af stereoisomere former i et hvilket som helst forhold eller et fysiologisk acceptabelt salt deraf eller et fysiologisk acceptabelt solvat af en hvilken som helst af disse.
2. Forbindelse med formel I ifølge krav 1, hvor R' , R", R"' er H; R1 er a) iso-butyl, sec-butyl, 1-ethylpropyl, 2-methylbutyl, 1,3-dimethylbutyl, l-isopropyl-2-methylpropyl; b) cyclopentyl, 2-methylcyclopentyl, cyclohexyl, 2- methylcyclohexyl, 2-(trifluormethyl)-cyclohexyl, 2- ethylcyclohexyl, cycloheptyl; c) methylencyclohexyl; d) phenyl, 2-chlorphenyl, 4-tolyl; R2 er a) 2-furanyl, 3-furanyl, 2-thienyl, 3-thienyl, 4-thiazolyl, 5-thiazoloyl, 1-pyrazolyl; 5-isoxazolyl, 5-methylthien-2-yl, 5-chlorthien-2-yl; b) phenyl; c) (C5-Cs)-cycloalkyl; eller d) 2-tetrahydrofuranyl ; R3 er H eller methyl; og R4 er a) (C3-C5)-alkyl, der eventuelt kan være substitueret med 1-3 F eller S-methyl, b) methylen-(C4-C6)-cycloalkyl; eller R3 og R4 sammen med carbonatomet, hvortil de er bundet, danner en 5- til 7-leddet cycloalkylring; R5 er H, methyl eller OH; R5 er H eller methyl; n er 0, 1 eller 2; og Z er CO2-R7, OR8, C (O) NR9R10, S (O) 2NR11R12,
hvor v er 0 eller 2; R7 er H; R8 er H eller (C1-C4)-alkyl; R9 er H, CH3; og R10 er a) H; b) (Ci-Cs) -alkyl, der er usubstitueret eller monosubstitueret med CF3; c) (C1-C2)-alkyl, der er substitueret med CN eller CO2R19; hvor R19 er H; d) (C2-C4) -alkyl, der er monosubstitueret med en substituent udvalgt fra gruppen, der består af S-CH3, SO2NR20R21, O-R22 og NR23R24; hvor R20 er H; R21 er H; R22 er H, (C1-C3)-alkyl, methylencyclopropyl, methylenphenyl eller methylen-2-tetrahydrofuran; R23 er H eller (C1-C2) -alkyl; R24 er (C1-C2) -alkyl eller SO2CH3; e) cyclobutyl, cyclopentyl eller 2-phenylcyclopropyl; f) (C0-C2)-alkylenheterocycloalkyl, hvor heterocycloalkyl er udvalgt fra gruppen, der består af 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydropyranyl, 3-tetrahydropyranyl, 4-tetrahydropyranyl og 1,4-dioxan-2-yl; g) (C2-C5)-alkylenheterocycloalkyl, hvor heterocycloalkyl er udvalgt fra gruppen, der består af 1-pyrrolidinyl, 1- piperidinyl, 1-azepanyl, 4-morpholinyl 1,1-dioxothiomorpholin-4-yl og 1-piperazinyl; hvor heterocycloalkyl er usubstitueret eller substitueret med 1 eller 2 substituenter udvalgt fra gruppen, der består af (C1-C2)-alkyl eller methylenphenyl; h) (C0-C3) -alkylenheterocycloalkyl, hvor heterocycloalkyl er udvalgt fra gruppen, der består af 3-pyrrolidinyl, 2- piperidinyl, 3-piperidinyl, 4-piperidinyl og 2-morpholinyl og hvor heterocycloalkyl er substitueret med en substituent udvalgt fra gruppen, der består af i) (C1-C4)-alkyl; ii) methylencyclohexyl; iii) (C0-C2) -alkylenphenyl; iv) (C0-C1) -alkylenpyridyl; v) pyrimidinyl; i) 8-methyl-8-aza-bicyclo[3.2.1]oct-3-yl; j) 9-methyl-9-aza-bicyclo[3.3.1]non-3-yl; k) methylen-4-(octahydroquinolizinyl); l) (Co-C2) -alkylenphenyl, hvor phenyl er usubstitueret eller monosubstitueret med substituenter udvalgt fra gruppen, der består af F, 0-CH3, N (013)2; m) (C1-C2)-alkylenheteroaryl, hvor heteroarylringen er udvalgt fra gruppen, der består af 2-thienyl, 2-furanyl, 2-thiazolyl, 2-oxazolyl, 5-tetrazolyl og 5-oxo-4,5-dihydro-lH- [1,2,4]triazol-3-yl; eller R9 og R10 sammen med N-atomet, der bærer dem, er a) azetidinyl substitueret med CO2H; b) pyrrolidinyl, der er usubstitueret eller monosubstitueret med en substituent udvalgt fra gruppen, der består af i) OH; ii) methylen-0CH3; iii) methylen-O-methylenphenyl; iv) CO2H; v) NR28R29, hvor R28 er (C1-C2) -alkyl, og R29 er (C1-C2) -alkyl; vi) 1-piperazinyl, der er usubstitueret eller monosubstitueret med methyl; c) piperidinyl, der er monosubstitueret med en substituent udvalgt fra gruppen, der består af i) 0- (C1-C3) alkyl; ii) methylen-0-CH3; iii) NR28R29, hvor R23 er (C1-C2)-alkyl, og R29 er methylenphenyl eller ethylen-N (CH3) 2; iv) 1-piperidinyl, der er monosubstitueret med methyl; v) 1-piperazinyl, der er usubstitueret eller monosubstitueret med methyl; vi) 4-morpholinyl; vii) 1-azepanyl; viii) 2-(2,3-dihydro-lH-isoindolyl); d) 4-morpholinyl, der er disubstitueret med methyl; e) 4-thiomorpholinyl; f) piperazinyl, der er monosubstitueret med en substituent udvalgt fra gruppen, der består af: i) (C1-C4) -alkyl; ii) (Cs-Ce) -cycloalkyl; iii) phenyl, der er usubstitueret eller monosubstitueret med F, CF3 eller OCH3; iv) methylenphenyl, der er usubstitueret eller disubstitueret på tilstødende positioner med gruppen -0((¾) 0-; v) pyridyl; g) azepanyl, der er substitueret med methylenphenyl, der er usubstitueret eller mono- eller disubstitueret med F eller Cl; c) en 2,5-diaza-bicyclo[2.2.1]heptylring, der er substitueret på det andet N-atom i 5-position med en substituent udvalgt fra gruppen, der består af (C1-C4) -alkyl, methylencyclopentyl, phenyl, der er monosubstitueret med F, methylenphenyl, hvor phenyl er usubstitueret eller monosubstitueret med OCH3 eller CF3; R11 er H; R12 er CHS; R13 er H; R14 er CF3 eller methylen-OCH3; R15 er cyclopryopyl eller phenyl; R16 er H eller CH3; R17 er H eller CH3; og R18 er CH3; i en hvilken som helst af dens stereoisomere former eller en blanding af stereoisomere former i et hvilket som helst forhold eller et fysiologisk acceptabelt salt deraf eller et fysiologisk acceptabelt solvat af en hvilken som helst af disse.
3. Forbindelse med formel I ifølge krav 1 eller 2, hvor R' , R", R"' er H; R1 er 1-ethylpropyl; R2 er 3-thienyl; R3 er H; R4 er 2-methylpropyl; n er 0, 1, 2; og Z er C (0) NR9R10.
4. Forbindelse med formel I ifølge krav 1 eller 2, hvor R' , R", R"' er H; R1 er 1-ethylpropyl eller 2-methylcyclohexyl; R2 er 3-thienyl; R3 er H eller (C1-C2)-alkyl; og R4 er a) (C3-C5)-alkyl, der eventuelt kan være substitueret med 1-3 F eller S-(C1-C4) -alkyl, b) (C0-C1)-alkylen-(C3-C7)-cycloalkyl, hvor cycloalkyl er usubstitueret eller mono- eller disubstitueret med methyl; eller R3 og R4 sammen med carbonatomet, hvortil de er bundet, danner en 5- til 7-leddet cycloalkylring, der er usubstitueret eller monosubstitueret med (C1-C4)-alkyl; n er 0; og Z er CO2-H.
5. Forbindelse med formel I ifølge krav 1 eller 2, hvor R' , R", R"' er H; R1 er 1-ethylpropyl eller 2-methylcyclohexyl; R2 er 3-thienyl; R3 er H eller (C1-C2)-alkyl; og R4 er a) (C3-C5)-alkyl, der eventuelt kan være substitueret med 1-3 F eller S-(C1-C4) -alkyl, b) (C0-C1)-alkylen-(C3-C7)-cycloalkyl, hvor cycloalkyl er usubstitueret eller mono- eller disubstitueret med methyl; eller R3 og R4 sammen med carbonatomet, hvortil de er bundet, danner en 5- til 7-leddet cycloalkylring, der er usubstitueret eller monosubstitueret med (C1-C4)-alkyl; R5 er H, (C1-C4) -alkyl eller OH; R6 er H eller (C1-C4)-alkyl; n er 1; og Z er CO2-H.
6. Forbindelse med formel I ifølge krav 1 eller 2, hvor R', R", R'" er H; R1 er 1-ethylpropyl eller 2-methylcyclohexyl; R2 er 3-thienyl; R3 er H eller (C1-C2)-alkyl ; og R4 er a) (C3-C5)-alkyl, der eventuelt kan være substitueret med 1-3 F eller S-(C1-C4) -alkyl, b) (C0-C1)-alkylen-(C3-C7)-cycloalkyl, hvor cycloalkyl er usubstitueret eller mono- eller disubstitueret med methyl; eller R3 og R4 sammen med carbonatomet, hvortil de er bundet, danner en 5- til 7-leddet cycloalkylring, der er usubstitueret eller monosubstitueret med (C1-C4)-alkyl; R5 er H, (C1-C4) -alkyl eller OH; R5 er H eller (C1-C4)-alkyl; n er 2 ; og Z er CO2-H.
7. Forbindelse med formel I ifølge krav 1 eller 2, hvor R', R", R'" er H; R1 er 1-ethylpropyl; R2 er 3-thienyl; R3 er H eller (C1-C2)-alkyl; og R4 er a) (C3-C5)-alkyl, der eventuelt kan være substitueret med 1-3 F eller S-(C1-C4) -alkyl, b) (C0-C1)-alkylen-(C3-C7)-cycloalkyl, hvor cycloalkyl er usubstitueret eller mono- eller disubstitueret med methyl; eller R3 og R4 sammen med carbonatomet, hvortil de er bundet, danner en 5- til 7-leddet cycloalkylring, der er usubstitueret eller monosubstitueret med (C1-C4)-alkyl; R5 er H, (C1-C4) -alkyl eller OH; R5 er H eller (C1-C4)-alkyl; n er 1 eller 2; og Z er OR8, S (0) 2NR11R12, CN,
> hvor v er O eller 2; R8 er H; R11 er H; R12 er CH3; og R13 er H.
8. Forbindelse med formel I ifølge krav 1 eller 2, hvor R' , R", R"' er H; R1 er 1-ethylpropyl; R2 er 3-thienyl; R3 er H; R4 er 2-methylpropyl; n er 0; og Z er C (0) NR9R10; hvor R9 er H eller methyl; og R10 er: c) (C1-C2)-alkyl, der er substitueret med CN; d) (C2-C4)-alkyl, der er monosubstitueret med en substituent udvalgt blandt NR23R24; hvor R23 er H; R24 er (C1-C2)-alkyl eller S02-methyl; m) (Ci-C2)-alkylenheteroaryl, hvor heteroarylringen er en 5-eller 6-leddet ring, der indeholder 1, 2, 3 eller 4 heteroatomer udvalgt blandt 0, S eller N; og hvor heteroarylringen er usubstitueret eller monosubstitueret med oxo (=0); eller R9 og R10 sammen med N-atomet, der bærer dem, er a) en 4-, 5- eller 6-leddet heterocylcoalkylring, der kun indeholder N-atomet, hvortil R9 og R10 er bundet, der er usubstitueret eller monosubstitueret med en substituent udvalgt fra gruppen, der består af i) (Co-Ci)-alkylen-OR26, hvor R26 er H; ii) CO2R27, hvor R27 er H.
9. Forbindelse med formel I ifølge krav 1 eller 2, der er udvalgt fra gruppen, der består af 1 1-{ [1- (1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-cycloheptancarboxylsyre 6 1-{[1-(-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol- 5-carbonyl]-amino}-cyclopentancarboxylsyre
3-Cyclopentyl-2-{[1-(1-ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 12 2-{[1-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-2,4-dimethylpentansyre 15 (S)-3-Cyclohexyl-2-{[1-(2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 16 (S)—2 —{ [1-(2-Methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-hexansyre 18 (S)—2—{ [1— (1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH- benzoimidazol-5-carbonyl]-amino}-hexansyre 21 (S)-3-Cyclopropyl-2-{[1-(1-ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 22 (S) -3-Cyclobutyl-2-{[1-(1-ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 2 3 (S) -3-Cyclobutyl-2- {[1-((1R,2R) -2-methylcyclohexyl) - 2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 24 l-{ [1- (1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH- benzoimidazol-5-carbonyl]-amino}-cyclohexancarboxylsyre 25 2-{[1-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-2-methylpentansyre 26 2-{ [1- (1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH- benzoimidazol-5-carbonyl]-amino}-5,5,5-trifluorpentansyre 27 5,5,5-Trifluor-2-{[l-((lR,2R) -2-methylcyclohexyl ) - 2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-pentansyre 29 3-(4,4-Dimethylcyclohexyl)-2-{[1-(1-ethylpropyl)-2- thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 33 3-(4,4-Dimethylcyclohexyl)-2-{[1-((IR,2R)-2-methy1cyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 34 1-{ [1- (1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino} - 4- methyleyelohexancarboxylsyre
4-Methyl-1-{[1—((1R,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}- eyelohexancarboxylsyre 36 2-{ [1- (1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-3-(4-methylcyclohexyl) -propionsyre 38 1—{[1—((IR,2R)-2-Methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-eyelohexancarboxylsyre
3-Cycloheptyl-2-{[1-(1-ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre
3-Cycloheptyl-2-{[1-((IR,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre
3-Cyclohexyl-3-{[1-(1-ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 45 3-{[1-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-heptansyre
4-Cyclohexyl-3-{[1-(1-ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-smørsyre 47 3-{[1- (1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-5,5-dimethylhexansyre 48 (R)—3—{[1—(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-5-methylhexansyre
4-Cyclohexyl-3-{[1-((1R,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethy1-lH-benzoimidazol-5-carbonyl]-amino}-smørsyre
4-Cyclohexyl-3-{[1-((IS,2S)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-smørsyre 53 (3R,4S)-4-Methyl-3-{[1—((1R,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}- hexansyre 54 (3R,4S)-3-{[l-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-4-methylhexansyre 55 3-{[1-((1R,2R)-2-Methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-hexansyre 56 3—{[1—((1R,2R)-2-Methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-heptansyre
3-Cyclohexyl-3-{[1-((IR,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 58 3-{ [ 1- (1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH- benzoimidazol-5-carbonyl]-amino}-2,2-dimethylheptansyre
4-Ethyl-3-{[1-(1-ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-hexansyre 60 (S)-4-Cyclopentyl-3-{[1-(1-ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-smørsyre 61 (S)-4-Cyclopentyl-3-{[1-((IR,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazo1-5-carbonyl]-amino}-smørsyre 62 3-{[1-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-2,2,5-trimethylhexansyre 63 3-{ [ 1-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-2,2-dimethylhexansyre 64 (1-{ [1- (1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH- benzoimidazol-5-carbonyl]-amino}-cyclohexyl)-eddikesyre 66 (1—{[1—((IR,2R)-2-Methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-cyclohexyl)-eddikesyre 67 (2R,3S)-3-{[1-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-2-hydroxy-5-methylhexansyre 68 (2S,3S)-3- { [1- (1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-2-hydroxy-5-methylhexansyre 70 (R)-6-Methyl-4-{[1-((1R,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-heptansyre 71 (4R,5S)-4-{[1-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-5-methylheptansyre 72 (4R,5S)-5-Methyl-4-{[1-((IR,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-heptansyre 73 (3R,4S)-5-Cyclohexyl-4-{[1-(1-ethylpropyl)-2-thiophen-2- ylmethyl-lH-benzoimidazol-5-carbonyl]-amino} - 3-hydroxypentansyre 74 (3R,4S)-5-Cyclohexyl-3-hydroxy-4-{[l-((lR,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-pentansyre 75 (3S,4S)-4-{[l - (1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-3-hydroxy-6-methylheptansyre 76 (3R,4S)-4-{[l-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-3-hydroxy-6-methylheptansyre 77 (3R, 4S)-3-Hydroxy-6-methyl-4-{[1-((IR,2R)-2-methy1cyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-heptansyre 78 (3S, 4S)-3-Hydroxy-6-methyl-4-{[1-((IR,2R)-2-methy1cyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazo1-5-carbonyl]-amino}-heptansyre 79 (3 S,4S)-5-Cyclohexyl-4-{[1-(1-ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino} - 3- hydroxypentansyre 91 (S)-2-{ [1-((IR, 2R)-2-Methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-pentansyre 92 (2 S,3S)-3-Methyl-2-{[1-((IR,2R)-2-methy1cyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-pentansyre 94 (S)—2—{ [1—(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-pentansyre 95 (S)—3—{ [1— (1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-5-methylhexansyre 101 (S)-5-Methyl-3-{[ 1-(2-methylcyclohexyl)-2-thiophen-2- ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-hexansyre 107 (S)—3—{ [1—(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH- benzoimidazol-5-carbonyl]-amino}-5-methylhexansyre 114 (S) -2-{ [1-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH- benzoimidazol-5-carbonyl]-amino}-4-methylpentansyre 121 (S)-2-{[1-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH- benzoimidazol-5-carbonyl]-amino}-3-methylpentansyre 123 (S)—2 — { [1—(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH- benzoimidazol-5-carbonyl]-amino}-4-methylsulfanyIsmørsyre 125 (S)-3-Cyclohexyl-2-{[1-(1-ethylpropyl)-2-thiophen-2- ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 130 (S)—2—{ [1—(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH- benzoimidazol-5-carbonyl]-amino}-5-methylhexansyre 139 (S)-4-Methyl-2-{[1-(2-methylcyclohexyl)-2-thiophen-3- ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-pentansyre 146 (S)-4-Methyl-2-{[1-(2-methylcyclohexyl)-2-thiophen-2- ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-pentansyre 153 (2S,3R)-2-{[l-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH- benzoimidazol-5-carbonyl]-amino}-3-methylpentansyre 155 3-{[1-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH- benzoimidazol-5-carbonyl]-amino}-hexansyre 161 (R)—3—{[1- (1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH- benzoimidazol-5-carbonyl]-amino}-4-methylpentansyre 162 (R)—4—{ [1—(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH- benzoimidazol-5-carbonyl]-amino}-5-methylhexansyre 163 (R)—4—{ [1—(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH- benzoimidazol-5-carbonyl]-amino}-6-methylheptansyre 412 (S)-4-Methyl-2-{[1-((IR,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-pentansyre 413 (S)-4-Methyl-2-{[1-((IS,2S)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-pentansyre 414 (S)-4-Methyl-2-{[1-((IR,2S)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino]-pentansyre 415 (S)-4-Methyl-2-{[1-((IS,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino]-pentansyre 420 (S) -2-{ [1-(2-Methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-hexansyre 421 (S) -2-{ [1-(2-Methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-hexansyre 422 (S)-2-{[1-(2-Methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-hexansyre 423 (S)-2-{[1-(2-Methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-hexansyre 424 (S)-3-Cyclohexyl-2-{[1-(2-methylcyclohexyl)-2-thiophen-2- ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 425 (S)-3-Cyclohexyl-2-{[1-(2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 426 (S)-3-Cyclohexyl-2-{[1-(2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 427 (S)-3-Cyclohexyl-2-{[1-(2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 436 (S) — 5 —Methyl — 3—{ [1-(2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-hexansyre 437 (S) -5 —Methyl-3—{[1-(2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-hexansyre 438 (S)-5-Methyl-3-{[1-(2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-hexansyre 439 (S)—5—Methyl—3—{[1-(2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-hexansyre 440 (R)-2-{[1-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-1H-benzoimidazol-5-carbonyl]-amino}-2,4-dimethylpentansyre 441 (S) -2-{ [1-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-2,4-dimethylpentansyre 442 3-Cyclopentyl-2-{[1-((IR,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 443 3-Cyclopentyl-2-{[1— ((IR,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 448 (S)-3-Cycloheptyl-2-{[1-(1-ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 449 (R)-3-Cycloheptyl-2-{[1-(1-ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 450 3-Cycloheptyl-2-{[1-((IR,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 451 3-Cycloheptyl-2-{[1-((IR,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}- propionsyre 452 (S)—3—{ [1—(1-Ethylpropyl)-2-thiophen-2-ylmethyl-1H-benzoimidazol-5-carbonyl]-amino}-heptansyre 453 (R)-3-{[1-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-1H- benzoimidazol-5-carbonyl]-amino}-heptansyre 454 (S)-4-Cyclohexyl-3-{[1-(1-ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-smørsyre 455 (R)-4-Cyclohexyl-3-{[1-(1-ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-smørsyre 456 4-Cyclohexyl-3-{[1-((IR,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-smørsyre 457 4-Cyclohexyl-3-{[1-((IR,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-smørsyre 458 3-{[1-((IR,2R)-2-Methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-hexansyre 459 3-{[l-((lR,2R)-2-Methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-hexansyre 460 3—{[1—((1R,2R)-2-Methy1cyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-heptansyre 461 3-{[l-((lR,2R)-2-Methy1cyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-heptansyre 462 3-Cyclohexyl-3-{[1-((IR,2R)-2-methylcyclohexyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 4 63 3-Cyclohexyl-3-{ [1-((IR, 2R)-2-methylcyclohexyl)-2- thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-propionsyre 464 (R)—3—{ [1—(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-2,2,5-trimethylhexansyre 465 (S)—3—{[1-(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-2,2,5-trimethylhexansyre 466 (R)—3—{ [1—(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-2,2-dimethylhexansyre 467 (S)—3—{ [1—(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-2,2-dimethylhexansyre 468 (S)—3—{ [1—(1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH-benzoimidazol-5-carbonyl]-amino}-2,2-dimethylheptansyre 469 (R)—3—{ [1— (1-Ethylpropyl)-2-thiophen-2-ylmethyl-lH- benzoimidazol-5-carbonyl]-amino}-2,2-dimethylheptansyre; et fysiologisk acceptabelt salt deraf eller et fysiologisk acceptabelt solvat deraf.
10. Farmaceutisk sammensætning, der omfatter mindst én forbindelse med formel I ifølge et hvilket som helst af kravene 1 til 9 eller et fysiologisk acceptabelt solvat af en hvilken som helst af disse, til anvendelse som et farmaceutikum.
11. Forbindelse med formel I ifølge et hvilket som helst af kravene 1 til 9 eller et fysiologisk acceptabelt salt deraf eller et fysiologisk acceptabelt solvat af en hvilken som helst af disse til anvendelse som et farmaceutikum.
12. Forbindelse med formel I ifølge et hvilket som helst af kravene 1 til 9 eller et fysiologisk acceptabelt salt deraf eller et fysiologisk acceptabelt solvat af en hvilken som helst af disse til anvendelse til forebyggelse og behandling af kardiovaskulære sygdomme, herunder koronar hjertesygdom, apopleksi, hjerteinsufficiens, systolisk hjerteinsufficiens, diastolisk hjerteinsufficiens, diabetisk hjerteinsufficiens, hjerteinsufficiens med bevaret ejektionsfraktion, kardiomyopati, myokardieinfarkt, venstre ventrikulær dysfunktion, venstre ventrikulær dysfunktion efter myokardieinfarkt, hjertehypertrofi, myokardiel remodellering, myokardiel remodellering efter infarkt eller efter hjerteoperation og hjerteklapsygdomme.
13. Forbindelse med formel I ifølge et hvilket som helst af kravene 1 til 9 eller et fysiologisk acceptabelt salt deraf eller et fysiologisk acceptabelt solvat af en hvilken som helst af disse til anvendelse til forebyggelse og behandling af metabolisk syndrom, insulinresistens, diabetes melittus, diabetiske senkomplikationer, diabetiske makro- og mikrovaskulopatier, diabetisk nefropati, diabetisk retinopati, diabetisk neuropatier og kardiel autonom neuropati.
14. Forbindelse med formel I ifølge et hvilket som helst af kravene 1 til 9 eller et fysiologisk acceptabelt salt deraf eller et fysiologisk acceptabelt solvat af en hvilken som helst af disse til anvendelse til forebyggelse og behandling af sygdomme med forstyrret kropsvæskehomeostase ved CNS-afhængige og -uafhængige effekter, akut og kronisk nyresvigt, hypertension, pulmonal hypertension, portal hypertension og systolisk hypertension.
15. Forbindelse med formel I ifølge et hvilket som helst af kravene 1 til 9 eller et fysiologisk acceptabelt salt deraf eller et fysiologisk acceptabelt solvat af en hvilken som helst af disse til anvendelse til forebyggelse og behandling af forøget vaskulær permeabilitet og ikke-fungerende blodkar, vaskulær hypertrofi, vaskulær remodellering, vaskulær stivhed, aterosklerose, perifer arteriel okklusiv sygdom (PAOD), restenose, trombose, vaskulære permeabilitetsforstyrrelser, iskæmi, reperfusionsskade, iskæmi og/eller reperfusionsskade af hjerte, nyre og retina.
Applications Claiming Priority (2)
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EP12306142 | 2012-09-21 | ||
PCT/EP2013/069432 WO2014044738A1 (en) | 2012-09-21 | 2013-09-19 | Benzoimidazole-carboxylic acid amide derivatives as apj receptor modulators |
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US (1) | US9156796B2 (da) |
EP (1) | EP2897939B1 (da) |
JP (1) | JP6186438B2 (da) |
KR (1) | KR20150058284A (da) |
CN (1) | CN104640846A (da) |
AU (1) | AU2013320323B2 (da) |
BR (1) | BR112015005972A2 (da) |
CA (1) | CA2885272A1 (da) |
CY (1) | CY1118973T1 (da) |
DK (1) | DK2897939T3 (da) |
ES (1) | ES2623528T3 (da) |
HR (1) | HRP20170628T1 (da) |
HU (1) | HUE031733T2 (da) |
IL (1) | IL237212A (da) |
LT (1) | LT2897939T (da) |
MX (1) | MX2015003653A (da) |
PL (1) | PL2897939T3 (da) |
PT (1) | PT2897939T (da) |
RU (1) | RU2015114772A (da) |
SG (1) | SG11201501051UA (da) |
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CY1118973T1 (el) | 2018-01-10 |
PL2897939T3 (pl) | 2017-08-31 |
IL237212A0 (en) | 2015-04-30 |
HUE031733T2 (en) | 2017-07-28 |
RU2015114772A (ru) | 2016-11-10 |
MX2015003653A (es) | 2015-09-25 |
JP2015532916A (ja) | 2015-11-16 |
JP6186438B2 (ja) | 2017-08-23 |
US20140094450A1 (en) | 2014-04-03 |
AU2013320323A1 (en) | 2015-04-16 |
SI2897939T1 (sl) | 2017-05-31 |
HRP20170628T1 (hr) | 2017-06-30 |
PT2897939T (pt) | 2017-05-04 |
CN104640846A (zh) | 2015-05-20 |
EP2897939B1 (en) | 2017-02-01 |
SG11201501051UA (en) | 2015-03-30 |
KR20150058284A (ko) | 2015-05-28 |
LT2897939T (lt) | 2017-05-10 |
ES2623528T3 (es) | 2017-07-11 |
WO2014044738A1 (en) | 2014-03-27 |
BR112015005972A2 (pt) | 2017-07-04 |
EP2897939A1 (en) | 2015-07-29 |
CA2885272A1 (en) | 2014-03-27 |
US9156796B2 (en) | 2015-10-13 |
IL237212A (en) | 2016-10-31 |
AU2013320323B2 (en) | 2018-03-15 |
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