HRP20141029T1 - Derivati pirazolopiridina kao inhibitori nadph oksidaze - Google Patents
Derivati pirazolopiridina kao inhibitori nadph oksidaze Download PDFInfo
- Publication number
- HRP20141029T1 HRP20141029T1 HRP20141029AT HRP20141029T HRP20141029T1 HR P20141029 T1 HRP20141029 T1 HR P20141029T1 HR P20141029A T HRP20141029A T HR P20141029AT HR P20141029 T HRP20141029 T HR P20141029T HR P20141029 T1 HRP20141029 T1 HR P20141029T1
- Authority
- HR
- Croatia
- Prior art keywords
- optionally substituted
- group
- pyrazolo
- dione
- pyridine
- Prior art date
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- 150000005229 pyrazolopyridines Chemical class 0.000 title claims 8
- 108010002998 NADPH Oxidases Proteins 0.000 title claims 3
- 102000004722 NADPH Oxidases Human genes 0.000 title claims 3
- 239000003112 inhibitor Substances 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- -1 cyano, hydroxy, mercapto Chemical class 0.000 claims 8
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 125000003107 substituted aryl group Chemical group 0.000 claims 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- SOWDNLOMIQWAKK-UHFFFAOYSA-N 4-ethyl-2-(4-fluorophenyl)-5-(2-methoxyethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C2=C(CC)N(CCOC)C(=O)C=C2NN1C1=CC=C(F)C=C1 SOWDNLOMIQWAKK-UHFFFAOYSA-N 0.000 claims 2
- STQHYZIEXCJXHE-UHFFFAOYSA-N 4-ethyl-2-(4-fluorophenyl)-5-(2-phenylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(F)=CC=3)C(=O)C2=C(CC)N1CCC1=CC=CC=C1 STQHYZIEXCJXHE-UHFFFAOYSA-N 0.000 claims 2
- DKRLZUYJVLRNKH-UHFFFAOYSA-N 4-ethyl-2-(4-fluorophenyl)-5-(3-morpholin-4-ylpropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(F)=CC=3)C(=O)C2=C(CC)N1CCCN1CCOCC1 DKRLZUYJVLRNKH-UHFFFAOYSA-N 0.000 claims 2
- SVWXTWPIDMRQBZ-UHFFFAOYSA-N 4-ethyl-2-(4-fluorophenyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(F)=CC=3)C(=O)C2=C(CC)N1CC1=CC=CC=N1 SVWXTWPIDMRQBZ-UHFFFAOYSA-N 0.000 claims 2
- JTHHUSZXKAATHK-UHFFFAOYSA-N 4-ethyl-2-(4-fluorophenyl)-5-morpholin-4-yl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(F)=CC=3)C(=O)C2=C(CC)N1N1CCOCC1 JTHHUSZXKAATHK-UHFFFAOYSA-N 0.000 claims 2
- HKCHGZRTXYMUOB-UHFFFAOYSA-N 4-ethyl-5-(3-morpholin-4-ylpropyl)-2-[4-(trifluoromethoxy)phenyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(OC(F)(F)F)=CC=3)C(=O)C2=C(CC)N1CCCN1CCOCC1 HKCHGZRTXYMUOB-UHFFFAOYSA-N 0.000 claims 2
- JHESKYYOWZPHPU-UHFFFAOYSA-N 4-ethyl-5-(3-morpholin-4-ylpropyl)-2-[4-(trifluoromethyl)phenyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(=CC=3)C(F)(F)F)C(=O)C2=C(CC)N1CCCN1CCOCC1 JHESKYYOWZPHPU-UHFFFAOYSA-N 0.000 claims 2
- GDXIFMQUTARHDA-UHFFFAOYSA-N 4-methyl-2-(2-methylphenyl)-5-(3-morpholin-4-ylpropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)N(CCCN3CCOCC3)C(=O)C=C2N1 GDXIFMQUTARHDA-UHFFFAOYSA-N 0.000 claims 2
- RYPVHNJGJGSXHH-UHFFFAOYSA-N 5-benzyl-4-ethyl-2-(4-fluorophenyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(F)=CC=3)C(=O)C2=C(CC)N1CC1=CC=CC=C1 RYPVHNJGJGSXHH-UHFFFAOYSA-N 0.000 claims 2
- 102100021217 Dual oxidase 2 Human genes 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 101000968308 Homo sapiens Dual oxidase 1 Proteins 0.000 claims 2
- 101000968305 Homo sapiens Dual oxidase 2 Proteins 0.000 claims 2
- 206010029155 Nephropathy toxic Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 125000004447 heteroarylalkenyl group Chemical group 0.000 claims 2
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 208000019423 liver disease Diseases 0.000 claims 2
- 230000007694 nephrotoxicity Effects 0.000 claims 2
- 231100000417 nephrotoxicity Toxicity 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- FDPVGRGPQDYSEQ-UHFFFAOYSA-N 2,4-diphenyl-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C=1C=CC=CC=1C1=C2C(=O)N(C=3C=CC=CC=3)NC2=CC(=O)N1CC1=CC=CN=C1 FDPVGRGPQDYSEQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- SCPLVJAUOOAQQS-UHFFFAOYSA-N 4-ethyl-2-(2-methoxyphenyl)-5-(3-morpholin-4-ylpropyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C(=CC=CC=3)OC)C(=O)C2=C(CC)N1CCCN1CCOCC1 SCPLVJAUOOAQQS-UHFFFAOYSA-N 0.000 claims 1
- MOCCDBAWHYEHAG-UHFFFAOYSA-N 4-ethyl-5-morpholin-4-yl-2-phenyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC=CC=3)C(=O)C2=C(CC)N1N1CCOCC1 MOCCDBAWHYEHAG-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- FJPUXMVNLPHRCZ-UHFFFAOYSA-N 4-methyl-2-(2-methylphenyl)-5-(pyridin-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CC1=CC=CC=C1N1C(=O)C2=C(C)N(CC=3N=CC=CC=3)C(=O)C=C2N1 FJPUXMVNLPHRCZ-UHFFFAOYSA-N 0.000 claims 1
- ICYYTFBMNVALJS-UHFFFAOYSA-N 4-methyl-2-phenyl-5-(2-phenylethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC=CC=3)C(=O)C2=C(C)N1CCC1=CC=CC=C1 ICYYTFBMNVALJS-UHFFFAOYSA-N 0.000 claims 1
- ISLQXEIRVZXLJA-UHFFFAOYSA-N 4-methyl-2-phenyl-5-(pyridin-3-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC=CC=3)C(=O)C2=C(C)N1CC1=CC=CN=C1 ISLQXEIRVZXLJA-UHFFFAOYSA-N 0.000 claims 1
- KQWPBXREZDLGMX-UHFFFAOYSA-N 4-methyl-2-phenyl-5-(thiophen-2-ylmethyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC=CC=3)C(=O)C2=C(C)N1CC1=CC=CS1 KQWPBXREZDLGMX-UHFFFAOYSA-N 0.000 claims 1
- JNUCVMRXTBMHRQ-UHFFFAOYSA-N 4-methyl-5-(2-morpholin-4-ylethyl)-2-phenyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC=CC=3)C(=O)C2=C(C)N1CCN1CCOCC1 JNUCVMRXTBMHRQ-UHFFFAOYSA-N 0.000 claims 1
- IXQAPEWDNTZIAO-UHFFFAOYSA-N 4-methyl-5-(oxolan-2-ylmethyl)-2-phenyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC=CC=3)C(=O)C2=C(C)N1CC1CCCO1 IXQAPEWDNTZIAO-UHFFFAOYSA-N 0.000 claims 1
- QAABOTJXRMFONY-UHFFFAOYSA-N 4-methyl-5-morpholin-4-yl-2-phenyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC=CC=3)C(=O)C2=C(C)N1N1CCOCC1 QAABOTJXRMFONY-UHFFFAOYSA-N 0.000 claims 1
- FUQPUNMXZOQPSS-UHFFFAOYSA-N 5-[2-(1h-indol-3-yl)ethyl]-4-methyl-1-[(3-methylphenyl)methyl]-2-phenylpyrazolo[4,3-c]pyridine-3,6-dione Chemical compound CC1=CC=CC(CN2C3=CC(=O)N(CCC=4C5=CC=CC=C5NC=4)C(C)=C3C(=O)N2C=2C=CC=CC=2)=C1 FUQPUNMXZOQPSS-UHFFFAOYSA-N 0.000 claims 1
- ZRJNMDXRJSUJDE-UHFFFAOYSA-N 5-[2-(1h-indol-3-yl)ethyl]-4-methyl-2-phenyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C2=C(C)N(CCC=3C4=CC=CC=C4NC=3)C(=O)C=C2NN1C1=CC=CC=C1 ZRJNMDXRJSUJDE-UHFFFAOYSA-N 0.000 claims 1
- AERIONKKSUDYPZ-UHFFFAOYSA-N 5-benzyl-2-(4-fluorophenyl)-4-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(F)=CC=3)C(=O)C2=C(C)N1CC1=CC=CC=C1 AERIONKKSUDYPZ-UHFFFAOYSA-N 0.000 claims 1
- ANKFMCUMWMEHBE-UHFFFAOYSA-N 5-benzyl-2-(4-methoxyphenyl)-4-methyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CC(OC)=CC=C1N1C(=O)C2=C(C)N(CC=3C=CC=CC=3)C(=O)C=C2N1 ANKFMCUMWMEHBE-UHFFFAOYSA-N 0.000 claims 1
- ZMSQJBSJAFLATO-UHFFFAOYSA-N 5-benzyl-4-methyl-2-(4-nitrophenyl)-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC(=CC=3)[N+]([O-])=O)C(=O)C2=C(C)N1CC1=CC=CC=C1 ZMSQJBSJAFLATO-UHFFFAOYSA-N 0.000 claims 1
- YSUAHWBNDNZDME-UHFFFAOYSA-N 5-benzyl-4-methyl-2-phenyl-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound O=C1C=C2NN(C=3C=CC=CC=3)C(=O)C2=C(C)N1CC1=CC=CC=C1 YSUAHWBNDNZDME-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 206010002199 Anaphylactic shock Diseases 0.000 claims 1
- 208000020084 Bone disease Diseases 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 1
- 208000004930 Fatty Liver Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 208000032456 Hemorrhagic Shock Diseases 0.000 claims 1
- 206010020853 Hypertonic bladder Diseases 0.000 claims 1
- 208000032376 Lung infection Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims 1
- 208000009722 Overactive Urinary Bladder Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000001647 Renal Insufficiency Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 206010049771 Shock haemorrhagic Diseases 0.000 claims 1
- 206010044541 Traumatic shock Diseases 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 229940126575 aminoglycoside Drugs 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 208000003455 anaphylaxis Diseases 0.000 claims 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 208000019425 cirrhosis of liver Diseases 0.000 claims 1
- 208000033679 diabetic kidney disease Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000037765 diseases and disorders Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 210000003027 ear inner Anatomy 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 210000005095 gastrointestinal system Anatomy 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 230000002008 hemorrhagic effect Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 206010022000 influenza Diseases 0.000 claims 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 claims 1
- 201000006370 kidney failure Diseases 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000006542 morpholinylalkyl group Chemical group 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 230000002314 neuroinflammatory effect Effects 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
- 208000020629 overactive bladder Diseases 0.000 claims 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 150000003058 platinum compounds Chemical class 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 208000002815 pulmonary hypertension Diseases 0.000 claims 1
- 230000001850 reproductive effect Effects 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 208000017520 skin disease Diseases 0.000 claims 1
- 230000007863 steatosis Effects 0.000 claims 1
- 231100000240 steatosis hepatitis Toxicity 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
- 238000011282 treatment Methods 0.000 claims 1
- 125000004953 trihalomethyl group Chemical group 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P11/06—Antiasthmatics
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- A61P11/08—Bronchodilators
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- A61P13/10—Drugs for disorders of the urinary system of the bladder
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- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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Claims (17)
1. Derivat pirazolopiridina opće formule (I):
[image]
naznačen time, što G1 označava H; G2 označava opcionalno supstituiranu fenil grupu; G3 je izabrano iz grupe koju čine H, opcionalno supstituirana C1-C6 alkil grupa, opcionalno supstituirana C2-C6 alkenil grupa, opcionalno supstituirana C2-C6 alkinil grupa, opcionalno supstituirana aril grupa, opcionalno supstituirana C1-C6 alkil aril grupa, opcionalno supstituirana aril alkil grupa, opcionalno supstituirana heteroaril grupa, opcionalno supstituirana C1-C6 alkil heteroaril grupa, opcionalno supstituirana heteroaril alkil grupa, opcionalno supstituirana C2-C6 alkenil aril grupa, opcionalno supstituirana aril alkenil grupa, opcionalno supstituirana C2-C6 alkenil heteroaril grupa, opcionalno supstituirana heteroaril alkenil grupa, opcionalno supstituirana C3-C8-cikloalkil grupa, opcionalno supstituirana heterocikloalkil grupa, opcionalno supstituirana C1-C6 alkil C3-C8-cikloalkil grupa, opcionalno supstituirana C3-C8-cikloalkil alkil grupa, opcionalno supstituirana C1-C6 alkil heterocikloalkil i opcionalno supstituirana heterocikloalkil alkil grupa; G4 je izabrano iz grupe koju čine H, opcionalno supstituirana C1-C6 alkil grupa, opcionalno supstituirana C2-C6 alkenil grupa, opcionalno supstituirana C2-C6 alkinil grupa, aril grupa, opcionalno supstituirana C1-C6 alkil aril grupa, opcionalno supstituirana aril alkil grupa, opcionalno supstituirana heteroaril grupa, opcionalno supstituirana C1-C6 alkil heteroaril grupa, opcionalno supstituirana heteroaril alkil grupa; opcionalno supstituirana C2-C6 alkenil aril grupa, opcionalno supstituirana aril alkenil grupa, opcionalno supstituirana C2-C6 alkenil heteroaril grupa, opcionalno supstituirana heteroaril alkenil grupa, opcionalno supstituirana C3-C8-cikloalkil grupa, opcionalno supstituirana heterocikloalkil grupa, opcionalno supstituirana C1-C6 alkil C3-C8-cikloalkil grupa, opcionalno supstituirana C3-C8-cikloalkil alkil grupa, opcionalno supstituirana C1-C6 alkil heterocikloalkil i opcionalno supstituirana heterocikloalkil alkil grupa; G5 označava H; kao i njegovi tautomeri, geometrijski izomeri, optički aktivne forme odnosno enantiomeri, dijastereoizomeri i racemski oblici i farmaceutski prihvatljive soli, a za upotrebu u vidu medikamenta, pri čemu je derivat naznačen i time, što izraz "supstituiran” označava grupe supstituirane sa od 1 do 5 supstituenata, a izabrane iz grupe koju čine "alkil", "alkenil", "alkinil", "C3-C8-cikloalkil", "heterocikloalkil", "alkil aril", "alkil heteroaril", "alkil cikloalkil", "alkil heterocikloalkil", "amino", "aminosulfonil", "amonij", "acil amino", "amino karbonil", "aril", "heteroaril", "sulfinil, "sulfonil", "alkoksi", "alkoksi karbonil", "karbamat", "sulfanil", halogena, "trihalometil", cijano, hidroksi, merkapto i nitro grupa.
2. Derivat za upotrebu prema patentnom zahtjevu 1, naznačen time, što je G2izabran iz grupe koju čine fenil, 4-fluorofenil, 4-metoksifenil, 4-nitrofenil, 2-klorofenil, 2-metilfenil, 4-(trifluorometil)fenil, 4 (trifluorometoksi)fenil, 2,5-difluorofenil i 2-metoksifenil grupa.
3. Derivat za upotrebu prema patentnim zahtjevima 1 ili 2, naznačen time, što G3 označava opcionalno supstituiranu C1-C6 alkil grupu.
4. Derivat za upotrebu prema patentnim zahtjevima 1 ili 2, naznačen time, što G3 označava metil grupu.
5. Derivat za upotrebu prema patentnim zahtjevima 1 ili 2, naznačen time, što G3 označava opcionalno supstituiranu fenil grupu.
6. Derivat za upotrebu prema bilo kojem od patentnih zahtjeva od 1 do 5, naznačen time, što je G4 izabran iz grupe koju čine opcionalno supstituirana C1-C6 alkil, opcionalno supstituirana C2-C6 alkenil i opcionalno supstituirana C2-C6 alkinil grupa.
7. Derivat za upotrebu prema bilo kojem od patentnih zahtjeva od 1 do 5, naznačen time, što je G4 izabran iz grupe koju čine opcionalno supstituirana aril alkil i opcionalno supstituirana heteroaril alkil grupa.
8. Derivat za upotrebu prema bilo kojem od patentnih zahtjeva od 1 do 5, naznačen time, što je G4 izabran iz grupe koju čine opcionalno supstituirana morfolinil alkil, opcionalno supstituirana piperazinil alkil, opcionalno supstituirana pirolidinil alkil i opcionalno supstituirana tetrahidrofuranil alkil grupa.
9. Derivat za upotrebu prema bilo kojem od patentnih zahtjeva od 1 do 5, naznačen time, što je G4 izabran iz grupe koju čine opcionalno supstituirana morfolinil propil, opcionalno supstituirana morfolinil etil, opcionalno supstituirana piperazinil etil, opcionalno supstituirana pirolidinil propil i opcionalno supstituirana tetrahidrofuranil metil grupa.
10. Derivat za upotrebu prema bilo kojem od patentnih zahtjeva od 1 do 9 izabran iz grupe koja slijedi:
4-metil-2-fenil-5-(tiofen-2-ilmetil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
5 -((furan-2-ilmetil)-4-metil-2-fenil-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-metil-2-fenil-5-(piridin-3-ilmetil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-metil-2-fenil-5-(2-feniletil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
5-[2-(1H-indol-3-il)etil]-4-metil-1-(3-metilbenzil)-2-fenil-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
1-((4-fluorobenzil)-5-[2-(1H-indol-3-il)etil]-4-metil-2-fenil-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
1-((2-klorobenzil)-4-metil-5-[3-(2-oksopirolidin-1-il)propil]-2-fenil-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
1-((4-klorobenzil)-5-[2-(1H-imidazol-4-il)etil]-4-metil-2-fenil-H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
5 -((1,3-benzodioksol-5-ilmetil)-4-metil-2-fenil-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
5-benzil-4-metil-2-fenil-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
5-benzil-2-(4-fluorofenil)-4-metil-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
5-benzil-2-(4-metoksifenil)-4-metil-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
5-benzil-4-metil-2-(4-nitrofenil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-metil-2-fenil-5-(tetrahidrofuran-2-ilmetil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
5-[2-(1H-indol-3-il)etil]-4-metil-2-fenil-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-metil-5-morfolin-4-il-2-fenil-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
5-benzil-4-etil-2-(4-fluorofenil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-etil-2-(4-fluorofenil)-5 -(2-feniletil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-etil-2-(4-fluorofenil)-5-morfolin-4-il-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-metil-5-(2-morfolin-4-iletil)-2-fenil-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-etil-5-morfolin-4-il-2-fenil-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
2 -((2-klorofenil)-4-metil-5-(piridin-2-ilmetil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-metil-2-(2-metilfenil)-5-(3-morfolin-4-ilpropil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-etil-2-(4-fluorofenil)-5-(piridin-2-ilmetil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-etil-2-(4-fluorofenil)-5-(3-morfolin-4-ilpropil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-etil-2-(4-fluorofenil)-5-(2-metoksietil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
2,4-difenil-5-(piridin-3-ilmetil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
2 -((2-klorofenil)-4-etil-5-(piridin-3-ilmetil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-metil-2-(2-metilfenil)-5-(piridin-2-ilmetil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-etil-5-(3-morfolin-4-ilpropil)-2-[4-(trifluorometil)fenil]-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-etil-5-(3-morfolin-4-ilpropil)-2-[4-(trifluorometoksi)fenil]-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
2 -((2,5-difluorofenil)-4-etil-5-(3-morfolin-4-ilpropil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion; i
4-etil-2-(2-metoksifenil)-5-(3-morfolin-4-ilpropil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion,
njihovi tautomeri, geometrijski izomeri, optički aktivni oblici tipa enantiomera, dijastereoizomera i racemskih oblika.
11. Farmaceutski pripravak koji sadrži najmanje jedan derivat prema bilo kojem od patentnih zahtjeva od 1 do 10 i njegov farmaceutski prihvatljiv nosač, diluent ili ekscipijens.
12. Derivata pirazolopiridina opće formule (I):
[image]
naznačen time, što su G1, G2, G3, G4 i G5 kao što je to definirano u bilo kojem od prethodnih patentnih zahtjeva, izabran iz grupe koja slijedi:
5-benzil-4-etil-2-(4-fluorofenil)-1H-pirazolo[4,3c]piridin-3,6(2H,5H)-dion;
4-etil-2-(4-fluorofenil)-5-(2-feniletil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-etil-2-(4-fluorofenil)-5-morfolin-4-il-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
2-((2-klorofenil)-4-metil-5-(piridin-2-ilmetil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-metil-2-(2-metilfenil)-5-(3-morfolin-4-ilpropil)1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-etil-2-(4-fluorofenil)-5-(piridin-2-ilmetil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-etil-2-(4-fluorofenil)-5-(3-morfolin-4-ilpropil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-etil-2-(4-fluorofenil)-5-(2-metoksietil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-etil-5-(3-morfolin-4-ilpropil)-2-[4-(trifluorometil)fenil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion;
4-etil-5-(3-morfolin-4-ilpropil)-2-[4-(trifluorometoksi)fenil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion; i
2-((2,5-difluorofenil)-4-etil-5-(3-morfolin-4-ilpropil)-1H-pirazolo[4,3-c]piridin-3,6(2H,5H)-dion,
njihovi tautomeri, geometrijski izomeri, optički aktivni oblici odnosno enantiomeri, dijastereoizomeri i racemski oblici, kao i njihove farmaceutski prihvatljive soli.
13. Derivat pirazolopiridina opće formule (I), naznačen time, što su G1, G2, G3, G4 i G5 kao što je to definirano u bilo kojem od prethodnih patentnih zahtjeva, njegovi tautomeri, geometrijski izomeri, optički aktivni oblici odnosno enantiomeri, dijastereoizomeri i racemski oblici, kao i njegove farmaceutski prihvatljive soli, za upotrebu u profilaksi ili tretmanu bolesti ili stanja izabranih iz grupe koju čine kardiovaskularni poremećaji, respiratorni poremećaji, metabolički poremećaji, poremećaji kože, poremećaji u kostima, neuroinflamatorni i/ili neurodegenerativni poremećaji, bolesti bubrega, reproduktivni poremećaji, bolesti koje utječu na oko i/ili leću oka i/ili stanja koja utiču na unutrašnje uho, inflamatorni poremećaji, bolesti jetre, bol, rak, alergijski poremećaji, traumatizmi, septički, hemoragijski i anafilaktički šok, bolesti ili poremećaji gastrointestinalnog sistema, kao i druge bolesti i poremećaji koje prati izmijenjena aktivnost nikotinamid adenin dinukleotid fosfat oksidaze (NADPH oksidaze).
14. Derivat pirazolopiridina za upotrebu prema patentnom zahtjevu 13, naznačen time, što je bolest ili poremećaj bubrega izabran iz grupe koju čine dijabetska nefropatija, zastoj rada bubrega, glomerulonefritis, aminoglikozidna nefrotoksičnost, nefrotoksičnost uzrokovana spojevima platine i hiperaktivnost mokraćnog mjehura.
15. Derivat pirazolopiridina za upotrebu prema patentnom zahtjevu 13, naznačen time, što je bolest ili poremećaj jetre izabran iz grupe koju čine fibroza jetre, fibroza uzrokovana alkoholom, steatoza i alkohol-nezavisan steatohepatitis.
16. Derivat pirazolopiridina za upotrebu prema patentnom zahtjevu 13, naznačen time, što je respiratorni poremećaj izabran iz grupe koju čine bronhijalna astma, bronhitis, alergijski rinitis, respiratorni sindrom odraslih, virusna infekcija pluća (gripa), plućna hipertenzija i kronična opstruktivna bolest pluća (HOBP).
17. Derivat pirazolopiridina za upotrebu prema patentnom zahtjevu 13, naznačen time, što poremećaj praćen izmijenjenom aktivnošću nikotinamid adenin dinukleotid fosfat oksidaze (NADPH oksidaze) predstavlja plućnu fibrozu.
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| US89628407P | 2007-03-22 | 2007-03-22 | |
| EP07109555A EP2002835A1 (en) | 2007-06-04 | 2007-06-04 | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
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| US (2) | US8389518B2 (hr) |
| EP (3) | EP2002835A1 (hr) |
| JP (2) | JP5715340B2 (hr) |
| CN (2) | CN105061422B (hr) |
| AU (1) | AU2008228186C1 (hr) |
| BR (1) | BRPI0808824B8 (hr) |
| CA (1) | CA2676954C (hr) |
| CY (2) | CY1113556T1 (hr) |
| DK (2) | DK2545918T3 (hr) |
| ES (2) | ES2512491T3 (hr) |
| HK (2) | HK1141734A1 (hr) |
| HR (2) | HRP20130143T1 (hr) |
| IL (1) | IL201009A (hr) |
| PL (2) | PL2139477T3 (hr) |
| PT (2) | PT2139477E (hr) |
| RS (2) | RS52640B (hr) |
| SI (2) | SI2545918T1 (hr) |
| WO (1) | WO2008113856A1 (hr) |
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-
2007
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2008
- 2008-03-20 EP EP08718102A patent/EP2139477B1/en active Active
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- 2008-03-20 PT PT121872543T patent/PT2545918E/pt unknown
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- 2008-03-20 DK DK12187254.3T patent/DK2545918T3/da active
- 2008-03-20 CN CN201510477495.1A patent/CN105061422B/zh active Active
- 2008-03-20 BR BRPI0808824A patent/BRPI0808824B8/pt active IP Right Grant
- 2008-03-20 WO PCT/EP2008/053390 patent/WO2008113856A1/en active Application Filing
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- 2008-03-20 CN CN200880009282.4A patent/CN101686967B/zh active Active
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- 2008-03-20 DK DK08718102.0T patent/DK2139477T3/da active
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- 2008-03-20 US US12/532,336 patent/US8389518B2/en active Active
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2009
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2010
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2013
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