DK2599771T3 - Naphthalenderivat - Google Patents

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DK2599771T3
DK2599771T3 DK11812583.0T DK11812583T DK2599771T3 DK 2599771 T3 DK2599771 T3 DK 2599771T3 DK 11812583 T DK11812583 T DK 11812583T DK 2599771 T3 DK2599771 T3 DK 2599771T3
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amino
substituted
naphthalene
sulfonic acid
ylazo
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DK11812583.0T
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Akira Kakizuka
Seiji Hori
Toshiyuki Shudo
Tomohiro Fuchigami
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Daito Chemix Corp
Univ Kyoto
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Claims (17)

1. Forbindelse repræsenteret ved følgende formel (I) eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf, til anvendelse ved behandling af en valosinholdig protein (VCP)-medieret sygdom:
(i) hvor: R er phenyl, pyridyl, quinolinyl eller thiophenyl, som hver især kan have én eller flere substituenter Ra; hvert Ra er uafhængigt valgt blandt halogen; alkyl; substitueret alkyl; alkenyl; substitueret alkenyl; alkynyl; substitueret alkynyl; aryl; substitueret aryl; cycloalkyl; substitueret cycloalkyl; cycloalkenyl; substitueret cycloalkenyl; heteroaryl; substitueret heteroaryl; heterocyclyl; substitueret heterocyclyl; amino; substitueret amino repræsenteret ved -NR21R22, hvor R21 og R22 uafhængigt er valgt blandt hydrogen, R30 og -SO2-R30, eller R21 og R22 danner, sammen med det nitrogen, hvormed de er forbundet, heterocyclyl eller substitueret heterocyclyl, under forudsætning af at R21 og R22 ikke samtidigt er hydrogen; cyano; nitro; acyl valgt blandt H-C(O)-, R30-C(O)- og NR27R28-NR26-C(0)- hvor R26, R27 og R28 uafhængigt er valgt blandt hydrogen, R30, -C(0)0-R3° og -SO2-R30, eller R27 og R28 danner, sammen med det nitrogen, hvormed de er forbundet, heterocyclyl eller substitueret heterocyclyl; acylamino repræsenteret ved -NR20C(O)-R30, hvor R20 er hydrogen, alkyl eller substitueret alkyl; alkoxy; substitueret alkoxy; carboxyl; carboxylester repræsenteret ved -C(0)0-R3°; thioacyl valgt blandt H-C(S)- og R30-C(S)-; thiocyanat; thiol; alkylthio; substitueret alkylthio; substitueret sulfonyl repræsenteret ved -SO2-R30; aminosulfonyl repræsenteret ved -SC>2NR23R24, hvor R23 og R24 uafhængigt er valgt blandt hydrogen, R30, hydroxy, alkoxy, substitueret alkoxy, amino, hvor den ovenfor definerede substituerede amino og den ovenfor definerede acylamino, eller R23 og R24 danner, sammen med det nitrogen, hvormed de er forbundet, heterocyclyl eller substitueret heterocyclyl; og aminocarbonyl repræsenteret ved -C(0)NR23R24, hvor R23 og R24 er som defineret ovenfor; R30 er valgt blandt alkyl, substitueret alkyl, alkenyl, substitueret alkenyl, alkynyl, substitueret alkynyl, aryl, substitueret aryl, cycloalkyl, substitueret cycloalkyl, cycloalkenyl, substitueret cycloalkenyl, heteroaryl, substitueret heteroaryl, heterocyclyl, og substitueret heterocyclyl; det ovenfor substituerede alkyl, substitueret alkenyl, substitueret alkynyl og substitueret alkoxy er uafhængigt substitueret med én eller flere substituenter Rb; hvert Rb er uafhængigt valgt blandt alkoxy; substitueret alkoxy; den ovenfor definerede acyl; den ovenfor definerede acylamino; acyloxy repræsenteret ved -C(0)0-R3°; amino; den ovenfor definerede substituerede amino; den ovenfor definerede aminocarbonyl; aminothiocarbonyl repræsenteret ved -C(S)NR23R24, hvor R23 og R24 er som defineret ovenfor; aminocarbonylamino repræsenteret ved -NR20C(O)NR23R24, hvor R20, R23 og R24 er som defineret ovenfor; aminothiocarbonylamino repræsenteret ved -NR20C(S)NR23R24, hvor R20, R23 og R24 er som defineret ovenfor; aminocarbonyloxy repræsenteret ved -0-C(0)NR23R24, hvor R23 og R24 er som defineret ovenfor; aminosulfonyl repræsenteret ved -SC>2NR23R24, hvor R23 og R24 er som defineret ovenfor; aminosulfonyloxy repræsenteret ved -0-SC>2NR23R24, hvor R23 og R24 er som defineret ovenfor; aminosulfonylamino repræsenteret ved -NR20-SC>2NR23R24, hvor R20, R23 og R24 er som defineret ovenfor; amidino repræsenteret ved -C(=NR25)NR23R24, hvor R25 er valgt blandt hydrogen, R30, hydroxy, alkoxy, substitueret alkoxy, amino, den ovenfor definerede substituerede amino og den ovenfor definerede acylamino, og R23 og R24 er som defineret ovenfor; aryl; substitueret aryl; aryloxy; substitueret aryloxy; arylthio; substitueret arylthio; azid; carboxyl; den ovenfor definerede carboxylester; (carboxylester)amino repræsenteret ved -NR20-C(O)O-R30, hvor R20 er som defineret ovenfor; (carboxylester)oxy repræsenteret ved -0-C(0)0-R3°, hvor R30 er som defineret ovenfor; cyano; cyanat; cycloalkyl; substitueret cycloalkyl; cycloalkyloxy; substitueret cycloalkyloxy; cycloalkylthio; substitueret cycloalkylthio; cycloalkenyl; substitueret cycloalkenyl; cycloalkenyloxy; substitueret cycloalkenyloxy; cycloalkenylthio; substitueret cycloalkenylthio; guanidino; substitueret guanidino repræsenteret ved -NR29C(=NR29)N(R29)2, hvor hvert R29 uafhængigt er valgt blandt hydrogen, alkyl, substitueret alkyl, aryl, substitueret aryl, heteroaryl, substitueret heteroaryl, heterocyclyl og substitueret heterocyclyl, eller to R29'ere forbundet med det samme guanidinonitrogenatom, danner, sammen med det nitrogen, hvortil de er forbundet, heterocyclyl eller substitueret heterocyclyl, underforudsætning af at i det mindste ét R29 ikke er hydrogen; halogen; hydroxy; hydroxyamino; alkoxyamino; hydrazino; substitueret hydrazino repræsenteret ved -NR26NR27R28, hvor R26, R27 og R28 er som defineret ovenfor; heteroaryl; substitueret heteroaryl; heteroaryloxy; substitueret heteroaryloxy; heteroarylthio; substitueret heteroarylthio; heterocyclyl; substitueret heterocyclyl; heterocyclyloxy; substitueret heterocyclyloxy; heterocyclylthio; substitueret heterocyclylthio; nitro; spirocycloalkyliden; SO3H; den ovenfor definerede substituerede sulfonyl, -OSO2-R30, den ovenfor definerede thioacyl; thiocyanat; thiol; alkylthio; og substitueret alkylthio; idet det ovenfor substituerede aryl, substitueret cycloalkyl, substitueret cycloalkenyl, substitueret heteroaryl og substitueret heterocyclyl uafhængigt er substituerede med én eller flere substituenter Rc; hvert Rc er uafhængigt valgt blandt oxo, thion, alkyl, substitueret alkyl, alkenyl, substitueret alkenyl, alkynyl, substitueret alkynyl, alkoxy, substitueret alkoxy, den ovenfor definerede acyl, den ovenfor definerede acylamino, den ovenfor definerede acyloxy, amino, den ovenfor definerede substituerede amino, aminocarbonyl, den ovenfor definerede aminothiocarbonyl, den ovenfor definerede aminocarbonylamino, den ovenfor definerede aminothiocarbonylamino, den ovenfor definerede aminocarbonyloxy, den ovenfor definerede aminosulfonyl, den ovenfor definerede aminosulfonyloxy, den ovenfor definerede aminosulfonylamino, den ovenfor definerede amidino, aryl, substitueret aryl, aryloxy, substitueret aryloxy, arylthio, substitueret arylthio, azid, carboxyl, den ovenfor definerede carboxylester, den ovenfor definerede (carboxylester)amino, den ovenfor definerede (carboxylester)oxy, cyano, cyanat, cycloalkyl, substitueret cycloalkyl, cycloalkyloxy, substitueret cycloalkyloxy, cycloalkylthio, substitueret cycloalkylthio, cycloalkenyl, substitueret cycloalkenyl, cycloalkenyloxy, substitueret cycloalkenyloxy, cycloalkenylthio, substitueret cycloalkenylthio, guanidino, den ovenfor definerede substituerede guanidino, halogen, hydroxy, hydroxyamino, alkoxyamino, hydrazino, den ovenfor definerede substituerede hydrazino, heteroaryl, substitueret heteroaryl, heteroaryloxy, substitueret heteroaryloxy, heteroarylthio, substitueret heteroarylthio, heterocyclyl, substitueret heterocyclyl, heterocyclyloxy, substitueret heterocyclyloxy, heterocyclylthio, substitueret heterocyclylthio, nitro, SO3H, den ovenfor definerede substituerede sulfonyl, sulfonyloxy, thioacyl, thiocyanat, thiol, alkylthio, og substitueret alkylthio; og når Rb eller Rc har en yderligere substituent, er den yderligere substituent som defineret ovenfor, underforudsætning af at Rb og Rc ikke har mere end tre substituenter.
2. Forbindelse eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf til anvendelse ifølge krav 1, hvor Ra er fraværende eller hvert Ra uafhængigt er valgt blandt halogen, alkyl, substitueret alkyl, alkenyl, substitueret alkenyl, aryl, substitueret aryl, heteroaryl, substitueret heteroaryl, heterocyclyl, substitueret heterocyclyl, cyano, nitro, acyl, acylamino, alkoxy, substitueret alkoxy, carboxyl, carboxylester, alkylthio, substitueret alkylthio, og aminocarbonyl, hvori den substituerede alkyl, substitueret alkenyl, substitueret aryl, substitueret heteroaryl, substitueret heterocyclyl, substitueret alkoxy og substitueret alkylthio uafhængigt er substituerede med én eller flere substituenter Rb eller Rc som defineret i krav 1.
3. Forbindelse til anvendelse ifølge krav 1 eller krav 2, som er en forbindelse repræsenteret ved følgende formel (II) eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf:
(i i) hvor m er et heltal fra 0 til 4.
4. Forbindelse til anvendelse ifølge krav 1 eller krav 2, som er en forbindelse repræsenteret ved følgende formel (III) eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf
(i i i) hvor n er et heltal fra 0 til 5.
5. Forbindelse eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf til anvendelse ifølge ethvert af de foregående krav, hvor hvert Ra er uafhængigt valgt blandt alkenyl, substitueret alkenyl, aryl, substitueret aryl, heteroaryl, substitueret heteroaryl, cyano, carboxylester, alkylthio, substitueret alkylthio og aminocarbonyl, hvor den substituerede alkenyl, substitueret aryl, substitueret heteroaryl og substitueret alkylthio er substitueret med én eller flere substituenter Rb eller Rc som defineret i krav 1.
6. Forbindelse eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf til anvendelse ifølge ethvert af de foregående krav, hvor den VCP-medierede sygdom er IBMPFD, en neurodegenerativ sygdom, en muskelsygdom, en knoglesygdom, en inflammatorisk sygdom, cystisk fibrose, en autoimmunsygdom, en viral infektion, en tumorsygdom, dyslipidæmi, hypertension, godartet prostatahyperplasi, kronisk obstruktiv pulmonær sygdom, hyppig vandladning, urininkontinens, irritabel tarmsyndrom, en allergisk sygdom, mavesår, tolvfingertarmssår, depression, angst, skizofreni, migræne, smerte eller opkast.
7. Forbindelse repræsenteret ved følgende formel (II) eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf:
(II) hvor: hvert Ra er uafhængigt valgt blandt halogen; alkyl eventuelt substitueret med 1,2 eller 3 halogensubstituenter; alkenyl eventuelt substitueret med 1,2 eller 3 substituenter valgt blandt aryl og cyano; aryl eventuelt substitueret med 1, 2 eller 3 substituenter valgt blandt halogen, alkyl, heterocyclyl, aryl, heteroaryl, acyl, cyano, alkoxy, aryloxy og hydroxyl; heteroaryl eventuelt substitueret med 1,2 eller 3 substituenter valgt blandt oxo og alkoxy; heterocyclyl; acyl; og alkoxy eventuelt substitueret med 1, 2 eller 3 substituenter valgt blandt halogen, heteroaryl, heterocyclyl og alkoxy; og m er et heltal fra 0 til 4.
8. Forbindelse eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf ifølge krav 7, hvor hvert Ra uafhængigt er aryl eventuelt substitueret med 1,2 eller 3 substituenter valgt blandt halogen, alkyl, heterocyclyl, aryl, heteroaryl, acyl, cyano, alkoxy, aryloxy og hydroxy.
9. Forbindelse eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf ifølge krav 7, hvor hvert Ra uafhængigt er heteroaryl eventuelt substitueret med 1, 2 eller 3 substituenter valgt blandt oxo og alkoxy.
10. Forbindelse eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf ifølge ethvert af kravene 7 til 9, hvor m er 0, 1 eller 2.
11. Forbindelse eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf ifølge krav 7, som er en forbindelse valgt blandt følgende forbindelser eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf: 4-amino-3-(pyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(6-methoxypyridin-3-ylazo)naphthalen-1-sulfonsyre; 3- (2-pyridinomethoxy-5-pyridinoazo)-4-amino-1-naphthalensulfonsyre; 4- amino-3-[6-(tetrahydrofuran-2-ylmethoxy)pyridin-3-ylazo]-1-naphthalensulfonsyre; 4-amino-3-[6-(2,2,2-trifluorethoxy)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(2-methoxyethoxy)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-(6-phenylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(6-p-tolylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(6-m-tolylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(6-o-tolylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(6-biphenyl-2-ylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(4-ethoxypyridin-3-ylazo)naphthalen-1-sulfonsyre; 3-[6-(2-acetylphenyl)pyridin-3-ylazo]-4-aminonaphthalen-1-sulfonsyre; 3-[6-(3-acetylphenyl)pyridin-3-ylazo]-4-aminonaphthalen-1-sulfonsyre; 3- [6-(4-acetylphenyl)pyridin-3-ylazo]-4-aminonaphthalensulfonsyre; 4- amino-3-(6-thiophen-2-ylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(6-thiophen-3-ylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-[6-(2,4-dichlorphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(2-chlorphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(3-chlorphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(4-chlorphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(2-methoxyphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(4-methoxyphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(2-isopropoxyphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(4-isopropoxyphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(2-phenoxyphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-(6-styrylpyridin-3-ylazo)naphthalensulfonsyre; 4-amino-3-(6-dibenzothiophen-4-ylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-[6-(3-methoxyphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(2,3-dimethylphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(2,5-dimethylphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(3,5-dimethylphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-(6-oxazol-2-ylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(6-naphthalen-1-ylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(6-dibenzofuran-4-ylpyridin-3-ylazo)naphthalen-1-sulfonsyre; methyl 4-{4-[5-(1-amino-4-sulfonaphthalen-2-ylazo)pyridin-2-yl]phenyl}-4-oxobutyrat; 4-amino-3-(6-benzo[b]thiophen-3-ylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(6-biphenyl-3-ylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-[6-(3-cyanophenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(4-cyanophenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(4-benzoylphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(2-propoxyphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(4-fluor-2-methylphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-(2-phenylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-([2,3']bipyridinyl-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-([2,3']bipyridinyl-5-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(4-methyl-[2,3']bipyridinyl-5-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-([3,2';6',3"]terpyridin-3'-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-[6-(5-fluor-2-propoxyphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(2-fluor-6-propoxyphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(4-fluor-2-propoxyphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(5-fluor-2-methylphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(2-fluor-5-methylphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(2-butoxyphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(2-hexyloxyphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(4-butylphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(2-hydroxyphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(2-isobutoxyphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(5-chlor-2-hydroxyphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(4-methylbiphenyl-2-yl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-(6-thianthren-1-ylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-[6-(4-fluor-2-methylphenyl)-5-methylpyridin-3-ylazo]naphthalen-1- sulfonsyre; 4-amino-3-(6-quinolin-8-ylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(6-dibenzothiophen-4-yl-5-methylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(6-biphenyl-2-yl-5-methylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(6-methoxy-5-phenylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(6-chlor-5-phenylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(5,6-diphenylpyridin-3-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-[6-(2,6-dimethylphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(3-formyl-2-isopropoxy-5-methylphenyl)pyridin-3-ylazo]naphthalen-1- sulfonsyre; 4-amino-3-[6-(3-formyl-2-butoxy-5-methylphenyl)pyridin-3-ylazo]naphthalen-1- sulfonsyre; 4-amino-3-[6-(2-butoxy-3-ethoxy-5-formylphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; og 4-amino-3-[6-(2-ethoxy-3-formyl-5-methylphenyl)pyridin-3-ylazo]naphthalen-1- sulfonsyre.
12. Forbindelse eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf ifølge krav 11, som er 4-amino-3-(6-phenylpyridin-3-ylazo)naphthalen-1 -sulfonsyre eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf.
13. Forbindelse eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf ifølge krav 11, som er 4-amino-3-(6-biphenyl-2-ylpyridin-3-ylazo)naphthalen-1 -sulfonsyre eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf.
14. Forbindelse eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf ifølge krav 11, som er 4-amino-3-[6-(4-fluor-2-methylphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf.
15. Forbindelse eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf ifølge krav 11, som er 4-amino-3-[6-(3-formyl-2-butoxy-5-methylphenyl)pyridin-3-ylazo]-naphthalen-1 -sulfonsyre eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf.
16. Forbindelse eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf ifølge krav 11, som er 4-amino-3-(6-dibenzothiophen-4-ylpyridin-3-ylazo)naphthalen-1-sulfonsyre eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf.
17. Forbindelse valgt blandt følgende forbindelser eller et oxid, et farmaceutisk acceptabelt salt eller solvat deraf: 4-amino-3-[6-(3-morpholin-4-ylmethylphenyl)pyridin-3-ylazo]naphthalen-1 -sulfonsyre; 4-amino-3-[6-(2-trifluormethylphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(4-trifluormethylphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(3-trifluormethylphenyl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(3,5-bistrifluormethylphenyl)pyridin-3-ylazo]naphthalensulfonsyre; 4-amino-3-{6-[2-(6-hydroxyhexyloxy)phenyl]pyridin-3-ylazo}naphthalen-1-sulfonsyre; 4-{2-[5-(1-amino-4-sulfonaphthalen-2-ylazo)pyridin-2-yl]phenoxy}smørsyre; 4-amino-3-{6-[2-(3-hydroxypropoxy)phenyl]pyridin-3-ylazo}naphthalen-1-sulfonsyre; 4-amino-3-{6-[2-(3-tert-butoxycarbonylaminopropoxy)phenyl]pyridin-3-ylazo}- naphthalen-1 -sulfonsyre; 4-amino-3-[6-(2-{3-[(2-chlorpyridin-3-carbonyl)amino]propoxy}phenyl)pyridin-3-ylazo]-naphthalen-1 -sulfonsyre; 4-amino-3-[6-(4'-chlor-4-methylbiphenyl-2-yl)pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-[6-(5,5-dioxo-5H-5A6-dibenzothiophen-4-yl)pyridin-3-ylazo]naphthalen-1- sulfonsyre; 4-amino-3-[6-(4,3', 5'-trimethylbiphenyl-2-yl)pyridin-3-ylazo]naphthalen-1 -sulfonsyre; 4-amino-3-[6-(3'-chlor-4-methylbiphenyl-2-yl)pyridin-3-ylazo]naphthalen-1 -sulfonsyre; 4-amino-3-[6-(2-{3-[(2-chlorpyridin-4-carbonyl)amino]propoxy}phenyl)pyridin-3-ylazo]-naphthalen-1 -sulfonsyre; 4-amino-3-(6-{2-[3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)propoxy]phenyl}pyridin-3-ylazo)-naphthalen-1 -sulfonsyre; 4-amino-3-{6-[3-(pyridin-3-ylmethoxy)dibenzothiophen-4-yl]pyridin-3-ylazo}naphthalen-1-sulfonsyre; 4-amino-3-[6-(3-{3-[(2-chlorpyridin-3-carbonyl)amino]propoxy}dibenzothiophen-4-yl)-pyridin-3-ylazo]naphthalen-1-sulfonsyre; 4-amino-3-{6-[3-(3-hydroxypropoxy)dibenzothiophen-4-yl]pyridin-3-ylazo}naphthalen-1-sulfonsyre; 4-amino-3-[6-(2-methylquinolin-8-yl)pyridin-3-ylazo]naphthalen-1 -sulfonsyre; 4-amino-3-(2-fluorphenylazo)naphthalen-1-sulfonsyre; 4-amino-3-[4-[(2-thienylcarbonyl)amino]phenylazo]-1-naphthalensulfonsyre; 4-amino-3-(3-fluorphenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(4-fluorphenylazo)naphthalen-1 -sulfonsyre; 4-amino-3-(2-cyanophenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(3-cyanophenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(4-cyanophenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(2,4-dichlorphenylazo)naphthalen-1 -sulfonsyre; 4-amino-3-(3,4-dichlorphenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(2,4-dibromphenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(2,4,6-tribromphenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(2,4-difluorphenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(2-brom-4-chlorphenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(4-chlor-2-cyanophenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(2-chlor-4-fluorphenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(4-methyl-2-nitrophenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(4-pyridin-3-ylphenylazo)-1-naphthalensulfonsyre; 2-{4-[4-(1-amino-4-sulfonaphthalen-2-ylazo)benzoylamino]benzyl}malonsyre; 4-amino-3-(4'-methylbiphenyl-4-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(3'-methylbiphenyl-4-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(4-isoquinolin-1-ylphenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(2,6-dibrom-4-pyridin-3-ylphenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(4-phenylcarbamoylphenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(3-benzoylphenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(4-benzoylphenylazo)naphthalen-1-sulfonsyre; 4-amino-3-[4-(pyridin-4-ylmethoxy)phenylazo]naphthalen-1-sulfonsyre; 4-amino-3-(2-methylsulfanylphenylazo)naphthalen-1-sulfonsyre; 4-amino-3-(4-methylsulfanylphenylazo)naphthalen-1-sulfonsyre; 4-amino-3-[4-(pyridin-3-ylmethoxy)phenylazo]naphthalen-1-sulfonsyre; 4-amino-3-[4-(pyridin-2-ylmethoxy)phenylazo]naphthalen-1-sulfonsyre; 4-amino-3-[3-(pyridin-2-ylmethoxy)phenylazo]naphthalen-1-sulfonsyre; 4-amino-3-[3-(pyridin-3-ylmethoxy)phenylazo]naphthalen-1-sulfonsyre; 4-amino-3-[3-(pyridin-4-ylmethoxy)phenylazo]naphthalen-1-sulfonsyre; 4-amino-3-[2-(pyridin-2-ylmethoxy)phenylazo]naphthalen-1-sulfonsyre; 4-amino-3-[2-(pyridin-4-ylmethoxy)phenylazo]naphthalen-1-sulfonsyre; 4-amino-3-[2-(pyridin-3-ylmethoxy)phenylazo]naphthalen-1-sulfonsyre; 4-amino-3-[4-(2-cyano-2-phenylvinyl)phenylazo]naphthalen-1-sulfonsyre; 4-amino-3-(2,4'-difluor-2'-methyl-diphenyl-4-ylazo)naphthalen-1-sulfonsyre; 4-amino-3-(quinolin-3-ylazo)naphthalen-1-sulfonsyre; methyl 3-(1-amino-4-sulfonaphthalen-2-ylazo)thiophen-2-carboxylat; og 4-amino-3-(quinolin-6-ylazo)naphthalen-1-sulfonsyre.
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