# US 2013/0158027 A1 · Pyrazolo pyridine derivatives as nadph oxidase inhibitors

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- Number: US 2013/0158027 A1
- Document ID: US20130158027A1
- Status: Published application
- Kind: A1
- Application number: 13/755,617
- Filed: 2013-01-31
- Published: 2013-06-20
- Earliest claimed: 2008-09-23
- Assignees: Genkyotex SA
- Inventors: PATRICK PAGE; MIKE ORCHARD; BENOIT LALEU; FRANCESCA GAGGINI
- Web page: https://patentgrep.com/patent/US20130158027A1

## CPC

- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61K 31/437: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A61K 31/444: containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
- A61K 31/4545: containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
- A61K 31/496: Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 13/12: of the kidneys
- A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives
- A61P 17/00: Drugs for dermatological disorders
- A61P 19/00: Drugs for skeletal disorders
- A61P 19/08: for bone diseases, e.g. rachitism, Paget's disease
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 27/02: Ophthalmic agents
- A61P 27/16: Otologicals
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 31/04: Antibacterial agents
- A61P 35/00: Antineoplastic agents
- A61P 37/08: Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14)
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 471/04: Ortho-condensed systems
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

The present invention is related to pyrazolo pyridine derivatives of Formula (I), pharmaceutical composition thereof and to their use for the treatment and/or prophylaxis of disorders or conditions related to Nicotinamide adenine dinucleotide phosphate oxidase (NADPH Oxidase).

## Claims

### Claim 1

A method for the treatment or prophylaxis of a patient suffering from cardiovascular disorders, respiratory disorders, metabolism disorders, skin disorders, bone disorders, neuroinflammatory and/or neurodegenerative disorders, kidney diseases, reproduction disorders, diseases affecting the eye and/or the lens and/or conditions affecting the inner ear, inflammatory disorders, liver diseases, pain, cancers, allergic disorders, traumatisms, septic, hemorrhagic and anaphylactic shock, disorders of the gastrointestinal system, angiogenesis, angiogenesis-dependent conditions and other diseases and disorders associated with Nicotinamide adenine dinucleotide phosphate oxidase (NADPH Oxidase), the method comprising administering a pyrazolo pyridine derivative according to Formula (I):
wherein G1 is selected from H; optionally substituted acyl; optionally substituted acyl C1-C6 alkyl; optionally substituted alkyl C3-C8-cycloalkyl alkyl; optionally substituted heterocycloalkyl alkyl; optionally substituted aryl alkyl; and optionally substituted heteroaryl alkyl; G2 is selected from —CHR1R2 and a saturated ring system selected from optionally substituted C3-C8-cycloalkyl and optionally substituted heterocycloalkyl; R1 and R2 are independently selected from H; optionally substituted alkoxy; optionally substituted alkoxy C1-C6 alkyl; optionally substituted amino; optionally substituted aminoalkyl; optionally substituted acyl; C1-C6 alkyl; optionally substituted C2-C6 alkenyl; optionally substituted C2-C6 alkynyl; optionally substituted aryl; optionally substituted C1-C6 alkyl aryl; optionally substituted aryl C1-C6 alkyl; optionally substituted heteroaryl; optionally substituted C1-C6 alkyl heteroaryl; optionally substituted heteroaryl C1-C6 alkyl; optionally substituted C2-C6 alkenyl aryl; optionally substituted aryl C2-C6 alkenyl; optionally substituted C2-C6 alkenyl heteroaryl; optionally substituted heteroaryl C2-C6 alkenyl; optionally substituted C3-C8-cycloalkyl; optionally substituted heterocycloalkyl; optionally substituted C1-C6 alkyl C3-C8-cycloalkyl; optionally substituted C3-C8-cycloalkyl C1-C6 alkyl; optionally substituted C1-C6 alkyl heterocycloalkyl and optionally substituted heterocycloalkyl C1-C6 alkyl; or —CHR1R2 form together a ring selected from optionally substituted C3-C8-cycloalkyl and optionally substituted heterocycloalkyl; G3 is selected from H; optionally substituted amino; optionally substituted aminoalkyl; optionally substituted aminocarbonyl; optionally substituted alkoxy; optionally substituted alkoxy C1-C6 alkyl; optionally substituted carbonyl; optionally substituted C1-C6 alkyl; optionally substituted C2-C6 alkenyl; optionally substituted C2-C6 alkynyl; optionally substituted aryl; optionally substituted aryl C1-C6 alkyl; optionally substituted heteroaryl; optionally substituted C1-C6 alkyl heteroaryl; optionally substituted heteroaryl C1-C6 alkyl; optionally substituted C2-C6 alkenyl aryl; optionally substituted aryl C2-C6 alkenyl; optionally substituted C2-C6 alkenyl heteroaryl; optionally substituted heteroaryl C2-C6 alkenyl; optionally substituted C3-C8-cycloalkyl; optionally substituted heterocycloalkyl; optionally substituted C1-C6 alkyl C3-C8-cycloalkyl; optionally substituted C3-C8-cycloalkyl C1-C6 alkyl; optionally substituted C1-C6 alkyl heterocycloalkyl and optionally substituted heterocycloalkyl C1-C6 alkyl; G4 is selected from H; optionally substituted acyl; optionally substituted acyl amino; optionally substituted acyl C1-C6 alkyl; optionally substituted C1-C6 alkyl; optionally substituted C2-C6 alkenyl; optionally substituted C2-C6 alkynyl; optionally substituted aryl; optionally substituted C1-C6 alkyl aryl; optionally substituted aryl C1-C6 alkyl; optionally substituted heteroaryl; optionally substituted C1-C6 alkyl heteroaryl; optionally substituted heteroaryl C1-C6 alkyl; optionally substituted C2-C6 alkenyl aryl; optionally substituted aryl C2-C6 alkenyl; optionally substituted C2-C6 alkenyl heteroaryl; optionally substituted heteroaryl C2-C6 alkenyl; optionally substituted C3-C8-cycloalkyl; optionally substituted heterocycloalkyl; optionally substituted C1-C6 alkyl C3-C8-cycloalkyl; optionally substituted C3-C8-cycloalkyl C1-C6 alkyl; optionally substituted C1-C6 alkyl heterocycloalkyl and optionally substituted heterocycloalkyl C1-C6 alkyl; G5 is selected from H; optionally substituted C1-C6 alkyl; optionally substituted C2-C6 alkenyl; optionally substituted C2-C6 alkynyl; optionally substituted aryl; optionally substituted C1-C6 alkyl aryl; optionally substituted aryl C1-C6 alkyl; optionally substituted heteroaryl; optionally substituted C1-C6 alkyl heteroaryl; optionally substituted heteroaryl C1-C6 alkyl; optionally substituted C2-C6 alkenyl aryl; optionally substituted aryl C2-C6 alkenyl; optionally substituted C2-C6 alkenyl heteroaryl; optionally substituted heteroaryl C2-C6 alkenyl; optionally substituted C3-C8-cycloalkyl; optionally substituted heterocycloalkyl; optionally substituted C1-C6 alkyl C3-C8-cycloalkyl; optionally substituted C3-C8-cycloalkyl C1-C6 alkyl; optionally substituted C1-C6 alkyl heterocycloalkyl and optionally substituted heterocycloalkyl C1-C6 alkyl; or a tautomer, geometrical isomer, optically active form as enantiomer, diastereomer and racemate forms or a pharmaceutically acceptable salt thereof, to a patient in need of treatment of said disease or condition.

### Claim 2 (depends on 1)

The method according to claim 1, wherein said disease or condition is selected from atherosclerosis, endothelial dysfunction, hypertension, cardiovascular complications of Type I or Type II diabetes, intimal hyperplasia, coronary heart disease, cerebral, coronary or arterial vasospasm, heart failure including congestive heart failure, peripheral artery disease, restenosis, trauma caused by a stent, stroke, ischemic attack, vascular complications such as after organ transplantation, myocardial infarction, hypertension, formation of atherosclerotic plaques, platelet aggregation, angina pectoris, aneurysm, aortic dissection, ischemic heart disease, cardiac hypertrophy, pulmonary embolus, thrombotic events including deep vein thrombosis, injury caused after ischemia by restoration of blood flow or oxygen delivery as in organ transplantation, open heart surgery, angioplasty, hemorrhagic shock, angioplasty of ischemic organs including heart, brain, liver, kidney, retina and bowel, bronchial asthma, bronchitis, allergic rhinitis, adult respiratory syndrome, cystic fibrosis, lung viral infection (influenza), pulmonary hypertension, idiopathic pulmonary fibrosis, chronic obstructive pulmonary diseases (COPD), hay fever, asthma, obesity, metabolic syndrome, Type II diabetes, psoriasis, eczema, dermatitis, wound healing, scar formation, osteoporosis, osteoporasis, osteosclerosis, periodontitis, hyperparathyroidism, Alzheimer's disease, Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis, epilepsy, muscular dystrophy, leukoencephalopathies, leukodystrophies, multiple sclerosis, progressive multifocal leukoencephalopathy (PML), myelopathies, diabetic nephropathy, renal failure, glomerulonephritis, nephrotoxicity of aminoglycosides and platinum compounds, hyperactive bladder, chronic kidney diseases or disorders, erectile dysfunction, fertility disorders, prostatic hypertrophy, benign prostatic hypertrophy, cataract, diabetic cataract, re-opacification of the lens post cataract surgery, diabetic, retinopathy, presbyacusis, tinnitus, Meniere's disease and other balance problems, utriculolithiasis, vestibular migraine, noise induced hearing loss, drug induced hearing loss (ototoxicity), inflammatory bowel disease, sepsis, septic shock, adult respiratory distress syndrome, pancreatitis, shock induced by trauma, bronchial asthma, allergic rhinitis, rheumatoid arthritis, chronic rheumatoid arthritis, arteriosclerosis, intracerebral hemorrhage, cerebral infarction, heart failure, myocardial infarction, psoriasis, cystic fibrosis, stroke, acute bronchitis, chronic bronchitis, acute bronchiolitis, chronic bronchiolitis, osteoarthritis, gout, myelitis, ankylosing spondylitis, Reuter syndrome, psoriatic arthritis, spondylarthritis, juvenile arthritis or juvenile ankylosing spondylitis, reactive arthritis, infectious arthritis or arthritis after infection, gonococcal arthritis, syphilitic arthritis, Lyme disease, arthritis induced by “angiitis syndrome,” polyarteritis nodosa, anaphylactic angiitis, Luegenec granulomatosis, rheumatoid polymyalgia, articular cell rheumatism, calcium crystal deposition arthritis, pseudogout, non-arthritic rheumatism, bursitis, tendosynovitis, epicondyle inflammation (tennis elbow), carpal tunnel syndrome, disorders by repetitive use (typing), mixed form of arthritis, neuropathic arthropathy, hemorrhagic arthritis, vascular peliosis, hypertrophic osteoarthropathy, multicentric reticulohistiocytosis, arthritis induced by specific diseases, blood pigmentation, sickle cell disease and other hemoglobin abnormality, hyperlipoproteinemia, dysgammaglobulinemia, hyperparathyroidism, acromegaly, familial Mediterranean fever, Bechet's disease, systemic autoimmune disease erythematosus, multiple sclerosis and Crohn's disease or diseases like relapsing polychondritis, chronic inflammatory bowel diseases (IBD), liver fibrosis, alcohol induced fibrosis, steatosis, non-alcoholic steatohepatitis, rheumatic arthritis, chronic rheumatoid arthritis, chlamydial arthritis, chronic absorptive arthritis, chylous arthritis, arthritis based on bowel disease, filarial arthritis, gonorrheal arthritis, gouty arthritis, hemophilic arthritis, hypertrophic arthritis, juvenile chronic arthritis, Lyme arthritis, neonatal foal arthritis, nodular arthritis, ochronotic arthritis, psoriatic arthritis, suppurative arthritis, hyperalgesia, inflammatory pain, fibrosarcoma, myxosarcoma, liposarcoma, chondrosarcoma, osteogenic sarcoma, chordoma, angiosarcoma, endothelium sarcoma, lymphangiosarcoma, lymphangioendothelioma, periosteoma, mesothelioma, Ewing's tumor, leiomyosarcoma, rhabdomyosarcoma, colon carcinoma, pancreatic cancer, breast cancer, ovarian cancer, renal cancer, prostatic carcinoma, squamous cell carcinoma, basal cell carcinoma, adenocarcinoma, sweat gland carcinoma, sebaceous gland carcinoma, papillary carcinoma, papillary adenocarcinoma, cystadenocarcinoma, medullary carcinoma, bronchogenic carcinoma, renal cell carcinoma, hepatocellular carcinoma, cholangiocarcinoma, choriocarcinoma, seminoma, embryonal carcinoma, Wilms' tumor, cervical cancer, orchioncus, lung cancer, small-cell lung cancer, lung adenocarcinoma, bladder cancer, epithelial cancer, gastric mucosa disorders, ischemic bowel disease management, enteritis/colitis, cancer chemotherapy, neutropenia, sprouting angiogenesis, intussusceptive angiogenesis, vasculogenesis, arteriogenesis and lymphangiogenesis.

### Claim 3 (depends on 1)

The method according to claim 1, wherein said disease or condition is selected from atherosclerosis, hypertension, cardiovascular complications of Type I or Type II diabetes, intimal hyperplasia, coronary heart disease, cerebral, coronary or arterial vasospasm, endothelial dysfunction, heart failure including congestive heart failure, peripheral artery disease, restenosis, trauma caused by a stent, stroke, ischemic attack, vascular complications such as after organ transplantation, myocardial infarction, hypertension, formation of atherosclerotic plaques, platelet aggregation, angina pectoris, aneurysm, aortic dissection, ischemic heart disease, cardiac hypertrophy, pulmonary embolus, thrombotic events including deep vein thrombosis, injury caused after ischemia by restoration of blood flow or oxygen delivery as in organ transplantation, open heart surgery, angioplasty, hemorrhagic shock, angioplasty of ischemic organs including heart, brain, liver, kidney, retina and bowel.

### Claim 4 (depends on 1)

The method according to claim 1, wherein said disease or condition is selected from bronchial asthma, bronchitis, allergic rhinitis, adult respiratory syndrome, cystic fibrosis, lung viral infection (influenza), pulmonary hypertension, idiopathic pulmonary fibrosis and chronic obstructive pulmonary diseases (COPD).

### Claim 5 (depends on 1)

The method according to claim 1, wherein said disease or condition is obesity, metabolic syndrome or Type II diabetes.

### Claim 6 (depends on 1)

The method according to claim 1, wherein said disease or condition is osteoporosis, osteoporasis, osteosclerosis, periodontitis, or hyperparathyroidism.

### Claim 7 (depends on 1)

The method according to claim 1, wherein said disease or condition is diabetic nephropathy, renal failure, glomerulonephritis, nephrotoxicity of aminoglycosides and platinum compounds or hyperactive bladder.

### Claim 8 (depends on 1)

The method according to claim 1, wherein said disease or condition is erectile dysfunction, fertility disorders, prostatic hypertrophy or benign prostatic hypertrophy.

### Claim 9 (depends on 1)

The method according to claim 1, wherein said disease or condition is cataracts, re-opacification of the lens post cataract surgery, or diabetic retinopathy.

### Claim 10 (depends on 1)

The method according to claim 1, wherein said disease or condition is inflammatory bowel disease, sepsis, septic shock, adult respiratory distress syndrome, pancreatitis, shock induced by trauma, bronchial asthma, allergic rhinitis, rheumatoid arthritis, chronic rheumatoid arthritis, arteriosclerosis, intracerebral hemorrhage, cerebral infarction, heart failure, myocardial infarction, psoriasis, cystic fibrosis, stroke, acute bronchitis, chronic bronchitis, acute bronchiolitis, chronic bronchiolitis, osteoarthritis, gout, myelitis, ankylosing spondylitis, Reuter syndrome, psoriatic arthritis, spondylarthritis, juvenile arthritis or juvenile ankylosing spondylitis, reactive arthritis, infectious arthritis or arthritis after infection, gonococcal arthritis, syphilitic arthritis, Lyme disease, arthritis induced by “angiitis syndrome,” polyarteritis nodosa, anaphylactic angiitis, Luegenec granulomatosis, rheumatoid polymyalgia, articular cell rheumatism, calcium crystal deposition arthritis, pseudogout, non-arthritic rheumatism, bursitis, tendosynovitis, epicondyle inflammation (tennis elbow), carpal tunnel syndrome, disorders by repetitive use (typing), mixed form of arthritis, neuropathic arthropathy, hemorrhagic arthritis, vascular peliosis, hypertrophic osteoarthropathy, multicentric reticulohistiocytosis, arthritis induced by specific diseases, blood pigmentation, sickle cell disease and other hemoglobin abnormality, hyperlipoproteinemia, dysgammaglobulinemia, hyperparathyroidism, acromegaly, familial Mediterranean fever, Bechet's disease, systemic autoimmune disease erythematosus, multiple sclerosis and Crohn's disease or diseases like relapsing polychondritis, chronic inflammatory bowel diseases (IBD).

### Claim 11 (depends on 1)

The method according to claim 1, wherein said disease or condition is liver fibrosis, alcohol induced fibrosis, steatosis or non-alcoholic steatohepatitis.

### Claim 12 (depends on 1)

The method according to claim 1, wherein said disease or condition is pulmonary fibrosis.

### Claim 13 (depends on 1)

The method according to claim 1, wherein said disease or condition is inflammatory pain.

### Claim 14 (depends on 1)

The method according to claim 1, wherein said disease or condition is fibrosarcoma, myxosarcoma, liposarcoma, chondrosarcoma, osteogenic sarcoma, chordoma, angiosarcoma, endothelium sarcoma, lymphangiosarcoma, lymphangioendothelioma, periosteoma, mesothelioma, Ewing's tumor, leiomyosarcoma, rhabdomyosarcoma, colon carcinoma, pancreatic cancer, breast cancer, ovarian cancer, renal cancer, prostatic carcinoma, squamous cell carcinoma, basal cell carcinoma, adenocarcinoma, sweat gland carcinoma, sebaceous gland carcinoma, papillary carcinoma, papillary adenocarcinoma, cystadenocarcinoma, medullary carcinoma, bronchogenic carcinoma, renal cell carcinoma, hepatocellular carcinoma, cholangiocarcinoma, choriocarcinoma, seminoma, embryonal carcinoma, Wilms' tumor, cervical cancer, orchioncus, lung cancer, small-cell lung cancer, lung adenocarcinoma, bladder cancer or epithelial cancer.

### Claim 15 (depends on 14)

The method according to claim 14, wherein the pyrazolo pyridine derivative is administered in combination with a co-agent useful in the treatment of cancer.

### Claim 16

A method for inhibiting angiogenesis in a patient suffering from angiogenesis or angiogenesis dependent disorder, wherein the method comprises administering an angiogenesis inhibitory dose of a compound of Formula (I) or a tautomer, geometrical isomer, optically active form as enantiomer, diastereomer and racemate forms or a pharmaceutically acceptable salt thereof, in a patient in need thereof.

### Claim 17 (depends on 1)

The method according to claim 1, wherein G1 is H.

### Claim 18 (depends on 1)

The method according to claim 1, wherein G2 is —CHR1R2; R1 and R2 are as defined in claim 1.

### Claim 19 (depends on 1)

The method according to claim 1, wherein G2 is a saturated ring system selected from optionally substituted C3-C8-cycloalkyl and optionally substituted heterocycloalkyl.

### Claim 20 (depends on 1)

The method according to claim 1, wherein G5 is H.

### Claim 21 (depends on 1)

The method according to claim 1, the pyrazolo pyridine derivative is selected from the following compounds:
2-benzyl-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
2-(4-chlorobenzyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
2-benzyl-4-methyl-5-[3-(trifluoromethoxy)phenyl]-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
2,4-dimethyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
2,4,5-trimethyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
5-(furan-2-ylmethyl)-2,4-dimethyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
5-(4-chlorobenzyl)-2,4-dimethyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-butyl-5-(4-chlorobenzyl)-2-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-butyl-2-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
5-(4-chlorobenzyl)-4-methyl-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
2-benzyl-4-butyl-5-(3,5-dimethoxybenzyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
2-benzyl-4-butyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
2-cyclohexyl-4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
2,4-dimethyl-5-(2-pyridin-2-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
2-(2-methoxyethyl)-4-methyl-5-(2-pyridin-2-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
2,4-dimethyl-5-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
5-(2-methoxyethyl)-4-methyl-2-(2-phenylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
2-(2-methoxyethyl)-4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
N-{3-[2-(2-methoxyethyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]phenyl}acetamide;
2-(2-methoxyethyl)-4-methyl-5-(2-morpholin-4-yl-2-oxoethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
2-benzyl-4-(3-methoxybenzyl)-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
2-benzyl-4-(3-methoxybenzyl)-5-(2-methoxyethyl)-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
2-(2,5-dichlorobenzyl)-5-(2-methoxyethyl)-4-methyl-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
2-[2-(4-chlorophenoxy)ethyl]-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
2-(2,5-dichlorobenzyl)-4-methyl-5-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
2-(2,5-dichlorobenzyl)-4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
5-(3,5-dimethoxybenzyl)-2-(2-methoxyethyl)-4-methyl-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
N-(3-{[4-methyl-3,6-dioxo-2-(2-phenylethyl)-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]methyl}phenyl)acetamide;
4-methyl-5-(2-morpholin-4-ylethyl)-2-(2-phenylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-2-(2-phenylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
2-(2-methoxyethyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
N-[2-(2-benzyl-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl)ethyl]-4-fluorobenzamide;
N-[3-(2-benzyl-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl)phenyl]acetamide;
N-(3-{[2-(2-chloro-4-fluorobenzyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]methyl}phenyl)acetamide;
5-[2-(4-benzylpiperazin-1-yl)-2-oxoethyl]-2-(2-methoxyethyl)-4-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
2-(2,5-dichlorobenzyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
2-(2-chloro-4-fluorobenzyl)-4-methyl-5-[2-(morpholin-4-ylmethyl)benzyl]-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
2-(2,5-dichlorobenzyl)-4-methyl-5-(2-morpholin-4-yl-2-oxoethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-methyl-2-(2-phenylethyl)-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
2-(2-chloro-4-fluorobenzyl)-4-methyl-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-fluoro-N-{2-[2-(2-methoxyethyl)-4-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]ethyl}benzamide;
5-[2-(4-benzylpiperazin-1-yl)-2-oxoethyl]-2-(2-chloro-4-fluorobenzyl)-4-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
5-benzyl-4-methyl-2-(1-methylpiperidin-4-yl)-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
4-methyl-2-(2-methylpropyl)-5-(pyridin-3-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
4-methyl-2-(2-methylpropyl)-5-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
5-(2,5-dichlorobenzyl)-4-methyl-2-(2-methylpropyl)-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
5-(2,4-dichlorobenzyl)-4-methyl-2-(2-methylpropyl)-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
5-(2,3-dihydro-1H-inden-1-yl)-4-methyl-2-(2-methylpropyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(3-chlorophenyl)-5-(2-morpholin-4-ylethyl)-2-(2-phenylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
2-benzyl-4-(3-chlorophenyl)-5-(2-methoxyethyl)-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
5-(4-chlorobenzyl)-4-[(4-fluorophenoxy)methyl]-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-[(4-fluorophenoxy)methyl]-5-(2-methoxyethyl)-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
5-(4-chlorobenzyl)-4-(3-chlorophenyl)-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(3-chlorophenyl)-2-(2-morpholin-4-ylethyl)-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
5-(4-chlorobenzyl)-4-(4-chlorophenyl)-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(4-chlorophenyl)-5-(4-methoxybenzyl)-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(4-chlorophenyl)-5-(3-methoxybenzyl)-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(4-chlorophenyl)-2,5-bis(2-methoxyethyl)-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
5-(4-chlorobenzyl)-4-(4-chlorophenyl)-2-(2-methoxyethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(4-chlorophenyl)-5-(2-methoxyethyl)-2-methyl-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
4-[(4-fluorophenoxy)methyl]-5-(4-methoxybenzyl)-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-[(4-fluorophenoxy)methyl]-2-(2-morpholin-4-ylethyl)-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(4-chlorophenyl)-5-(2-morpholin-4-ylethyl)-2-(2-phenylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(4-chlorophenyl)-5-(3-methoxybenzyl)-2-(2-methoxyethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(4-chlorophenyl)-2-(2-methoxyethyl)-5-[2-(morpholin-4-ylmethyl)benzyl]-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(4-chlorophenyl)-2-(2-methoxyethyl)-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(4-chlorophenyl)-5-(3-ethoxypropyl)-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
5-(2-methoxyethyl)-4-methyl-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(4-chlorophenyl)-5-(2-methoxyethyl)-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(3,4-dichlorophenyl)-2-(2-methoxyethyl)-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(3,4-dichlorophenyl)-5-(2-methoxyethyl)-2-methyl-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
4-(4-chlorophenyl)-5-methyl-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
5-methyl-2-(2-morpholin-4-ylethyl)-4-(3-phenoxypropyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
5-(2-methoxyethyl)-2-(2-morpholin-4-ylethyl)-4-(3-phenoxypropyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-[(4-fluorophenoxy)methyl]-2-(2-methoxyethyl)-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-[(4-chlorophenoxy)methyl]-5-(2-methoxyethyl)-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(4-chlorophenyl)-2-(2-methoxyethyl)-5-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(4-chlorophenyl)-2-(2-morpholin-4-ylethyl)-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-[(4-fluorophenoxy)methyl]-5-(3-methoxybenzyl)-2-(2-methoxyethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-methyl-2-(2-morpholin-4-ylethyl)-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(4-chlorophenyl)-5-methyl-2-(1-methylpiperidin-4-yl)-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
4-(4-chlorophenyl)-2-[2-(dimethylamino)ethyl]-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
5-(3-methoxybenzyl)-4-methyl-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
2-(2-morpholin-4-ylethyl)-4-(3-phenoxypropyl)-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(3-chlorophenyl)-5-(3-ethoxypropyl)-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-[(4-fluorophenoxy)methyl]-5-methyl-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-[(4-chlorophenoxy)methyl]-5-(3-ethoxypropyl)-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-[(benzyloxy)methyl]-5-(3-methoxybenzyl)-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-[(benzyloxy)methyl]-5-(3-ethoxypropyl)-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
5-(3-ethoxypropyl)-4-[(4-fluorophenoxy)methyl]-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-[(4-chlorophenoxy)methyl]-2-(2-morpholin-4-ylethyl)-5-(pyridin-2-ylmethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(4-chlorophenyl)-2-(2-morpholin-4-ylethyl)-5-(2-pyridin-2-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-[(4-fluorophenoxy)methyl]-2-(2-morpholin-4-ylethyl)-5-(2-pyridin-2-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
2,5-bis(2-methoxyethyl)-4-(3-phenoxypropyl)-1H-pyrazolo[4,3-c]pyridine-3,6 (2H,5H)-dione;
4-[(4-chlorophenoxy)methyl]-5-(3-methoxybenzyl)-2-(2-morpholin-4-ylethyl)-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
4-(3,5-dichlorophenyl)-5-(2-methoxyethyl)-2-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
5-[(4-benzylmorpholin-2-yl)methyl]-4-(4-chlorophenyl)-2-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
5-[(1-acetylpiperidin-4-yl)methyl]-4-(4-chlorophenyl)-2-methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione;
tert-butyl 4-{[4-(4-chloro phenyl)-2-methyl-3,6-dioxo-1,2,3,6-tetrahydro-5H-pyrazolo[4,3-c]pyridin-5-yl]methyl}piperidine-1-carboxylate; or
4-(4-chlorophenyl)-2-methyl-5-[(5-oxopyrrolidin-3-yl)methyl]-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione.