875781-17-2

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-1H-pyrazolo[3,4-b]pyridine is used as a synthetic building block for the preparation of 7-deazainazole chalcone derivatives, which exhibit analgesic and anti-inflammatory properties. These derivatives have potential applications in the development of new drugs for pain relief and inflammation management.
Used in Organic Synthesis:
As a pyridine derivative, 5-Bromo-1H-pyrazolo[3,4-b]pyridine can be utilized in various organic synthesis processes to create a wide range of chemical compounds. Its unique structure and functional groups make it a versatile component in the synthesis of complex organic molecules, which can be further explored for potential applications in various industries.

InChI:InChI=1/C7H7N3/c1-5-2-6-4-9-10-7(6)8-3-5/h2-4H,1H3,(H,8,9,10)

Synthetic route

5-bromo-2-fluoro-pyridine-3-carbaldehyde (875781-15-0) → 5-bromo-7-azaindazole (875781-17-2)

Conditions	Yield
With hydrazine hydrate In water at 65℃; for 15h; Inert atmosphere;	82%
With hydrazine In ethanol Heating / reflux;	46%
With hydrazine hydrate In ethanol at 100℃; for 8h;	40%

C12H18BrN3O2*ClH → 5-bromo-7-azaindazole (875781-17-2)

Conditions	Yield
Stage #1: C12H18BrN3O2*ClH With hydrogenchloride In ethanol; water at 20 - 65℃; for 16h; Stage #2: With sodium carbonate In ethanol; water	50%

2-Bromo-malonaldehyde (2065-75-0) + 3(5)-aminopyrazole (1225387-53-0) → 5-bromo-7-azaindazole (875781-17-2)

Conditions	Yield
In acetic acid for 6h; Heating; Reflux; Inert atmosphere of N2;	25%

2-Bromo-malonaldehyde (2065-75-0) + 3(5)-aminopyrazole (1225387-53-0) → 6-bromo-pyrazolo[1,5-α]pyrimidine (705263-10-1) + 5-bromo-7-azaindazole (875781-17-2)

Conditions	Yield
In ethanol at 20℃; Heating / reflux;	A 13.8% B 2.1%

3-aminopyrazole (1820-80-0) + 2-Bromo-malonaldehyde (2065-75-0) → 5-bromo-7-azaindazole (875781-17-2)

Conditions	Yield
With acetic acid for 2h; Heating / reflux;	11%

C8H10BrN3O2*ClH (875781-16-1) → 5-bromo-7-azaindazole (875781-17-2)

Conditions	Yield
Stage #1: C8H10BrN3O2*ClH With hydrogenchloride In ethanol; water at 20 - 65℃; for 16h; Stage #2: With sodium hydrogencarbonate In ethanol; water pH=8;

5-bromo-3-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-2(1H)-pyridinone hydrazone (1083326-08-2) → 5-bromo-7-azaindazole (875781-17-2)

Conditions	Yield
With hydrogenchloride; water In ethanol at 20 - 60℃;

5-bromo-2-fluoropyridine (766-11-0) → 5-bromo-7-azaindazole (875781-17-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C 1.2: 0.17 h / -78 °C 2.1: hydrazine hydrate / ethanol / 8 h / 100 °C View Scheme
Multi-step reaction with 2 steps 1.1: diisopropylamine; n-butyllithium / tetrahydrofuran / 3 h / -65 - -30 °C / Inert atmosphere 1.2: 0.08 h 2.1: hydrazine hydrate / tetrahydrofuran; ethanol; water / 1 h / 45 - 80 °C / Large scale View Scheme
Multi-step reaction with 2 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -90 - -85 °C 1.2: 0.5 h / -80 °C 2.1: hydrazine hydrate / ethanol / 12 h / 75 - 80 °C View Scheme

3,4-dihydro-2H-pyran (110-87-2) + 5-bromo-7-azaindazole (875781-17-2) → 5-bromo-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridine

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane; acetonitrile at 20℃; for 24h;	100%
With toluene-4-sulfonic acid In toluene at 100℃; for 4h;	98%
With toluene-4-sulfonic acid at 25 - 30℃; for 3h;	60.7%

5-bromo-7-azaindazole (875781-17-2) → 5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine (875781-18-3)

Conditions	Yield
Stage #1: 5-bromo-7-azaindazole With iodine; potassium hydroxide In N,N-dimethyl-formamide for 3.5h; Stage #2: With iodine; sodium hydroxide In 1,4-dioxane at 40℃; for 23h;	97%
Stage #1: 5-bromo-7-azaindazole With potassium hydroxide In N,N-dimethyl-formamide for 0.166667h; Stage #2: With iodine In N,N-dimethyl-formamide at 20℃; for 3.5h;	96%
Stage #1: 5-bromo-7-azaindazole With iodine; potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With iodine In N,N-dimethyl-formamide at 45℃; for 1h;	92%

5-bromo-7-azaindazole (875781-17-2) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

Conditions	Yield
With dmap; triethylamine In acetonitrile at 20℃; for 3.25h; Inert atmosphere;	93%
With dmap; triethylamine In dichloromethane at 20℃; for 24h;	85%
With dmap In tetrahydrofuran for 14h; Reflux;	68%

5-bromo-7-azaindazole (875781-17-2) + hexamethylenetetramine (100-97-0) → 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carbaldehyde

Conditions	Yield
With acetic acid In water for 12h; Sommelet Aldehyde Synthesis; Reflux;	92%

5-bromo-7-azaindazole (875781-17-2) → 5-bromo-1H-pyrazolo[3,4-b]pyridine 7-oxide

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In ethyl acetate at 20 - 50℃; for 5.5h;	91%
With dihydrogen peroxide; trifluoroacetic acid at 60℃; for 12h;

zinc(II) cyanide (557-21-1) + 5-bromo-7-azaindazole (875781-17-2) → 1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In 1-methyl-pyrrolidin-2-one at 92℃; for 5h; Temperature;	90%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl acetamide; water at 80℃; for 6h; Inert atmosphere;	82%
With tris-(dibenzylideneacetone)dipalladium(0); XPhos In water; N,N-dimethyl-formamide at 100℃; for 12h; Inert atmosphere;	82%
With tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 85℃; for 10h; Inert atmosphere; Large scale;	535 g

5-bromo-7-azaindazole (875781-17-2) + [3-(morpholin-4-ylcarbonyl)phenyl]boronic acid (723281-55-8) → morpholin-4-yl-[3-(1H-pyrazolo[3,4-b]pyridin-5-yl)-phenyl]-methanone (875781-22-9) + Triphenylphosphine oxide (791-28-6)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 175℃; for 1h; Microwave irradiation;	A 80% B 20%

5-bromo-7-azaindazole (875781-17-2) + p-methoxybenzyl chloride (824-94-2) → 5-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine (1111638-35-7)

Conditions	Yield
Stage #1: 5-bromo-7-azaindazole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: p-methoxybenzyl chloride In N,N-dimethyl-formamide at 0 - 20℃;	77.2%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	68.3%

5-bromo-7-azaindazole (875781-17-2) + trimethylsilylacetylene (1066-54-2) → 5-((trimethylsilyl) ethynyl)-1H-pyrazolo[3,4-b]pyridine (1207351-08-3)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	73.7%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere;	73.7%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile for 20h; Reflux; Inert atmosphere;	63%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In acetonitrile at 20 - 100℃; for 20h; Sonogashira Cross-Coupling; Inert atmosphere;
With copper(l) iodide; palladium bis[bis(diphenylphosphino)ferrocene] dichloride; triethylamine In N,N-dimethyl-formamide at 70℃; for 2h; Inert atmosphere;	3.5 g

5-bromo-7-azaindazole (875781-17-2) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → 5-bromo-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazolo[3,4-b]pyridine (1186608-66-1)

Conditions	Yield
Stage #1: 5-bromo-7-azaindazole With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide at 20℃; for 0.5h;	73%
Stage #1: 5-bromo-7-azaindazole With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.166667h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In tetrahydrofuran; mineral oil at 20℃;	43%
Stage #1: 5-bromo-7-azaindazole With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 0.416667h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil at 0℃; for 2h; Stage #3: With ammonium chloride In water; N,N-dimethyl-formamide; mineral oil Cooling;

5-bromo-7-azaindazole (875781-17-2) + methyl iodide (74-88-4) → 5-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine (887115-56-2)

Conditions	Yield
Stage #1: 5-bromo-7-azaindazole With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Stage #2: methyl iodide at 25℃; Inert atmosphere;	73%

5-bromo-7-azaindazole (875781-17-2) + propane-1-sulfonic acid {2,4-difluoro-3-[5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-amide (1312942-04-3) → propane-1-sulfonic acid {2,4-difluoro-3-[5-(1H-pyrazolo[3,4-b]pyridin-5-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl]-phenyl}-amide (1312939-70-0)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water; acetonitrile at 145℃; for 0.75h; microwave irradiation;	72%

5-bromo-7-azaindazole (875781-17-2) + methyl iodide (74-88-4) → 5-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine (887115-56-2) + 5-bromo-2-methyl-2H-pyrazolo[3,4-b]pyridine

Conditions	Yield
With sodium hexamethyldisilazane In tetrahydrofuran at 20℃; for 2h;	A 7% B 69%
With sodium hexamethyldisilazane In tetrahydrofuran; dimethyl sulfoxide at 20℃; for 3h;	A 46% B 3%

5-bromo-7-azaindazole (875781-17-2) + 2-(tert-butyldimethylsilyloxy)ethyl bromide (86864-60-0) → 5-bromo-1-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-pyrazolo[3,4-b]pyridine

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 18 - 25℃;	66%

N-iodo-succinimide (516-12-1) + 5-bromo-7-azaindazole (875781-17-2) → 5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine (875781-18-3)

Conditions	Yield
In 1,2-dichloro-ethane Reflux;	65.8%

5-bromo-7-azaindazole (875781-17-2) + [3-(methoxycarbonyl)phenyl]boronic acid (99769-19-4) → methyl 3-(1H-pyrazolo[3,4-b]pyridin-5-yl)benzoate (875781-27-4)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 110℃; for 15h; Microwave irradiation;	65%

5-bromo-7-azaindazole (875781-17-2) + N-(3-ethynyl-2,4-difluborophenyl)pyridine-3-ylsulfonamide → N-(3-((1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)-2,4-difluorophenyl)pyridine-3-sulfonamide

Conditions	Yield
With copper(l) iodide; tri-tert-butyl phosphine; potassium carbonate; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; toluene at 120℃; for 24h; Sonogashira Cross-Coupling; Sealed tube; Inert atmosphere;	64%

5-bromo-7-azaindazole (875781-17-2) + 2,4-difluoro-3-ethynylaniline → 3-((1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)-2,4-difluoroaniline

Conditions	Yield
With copper(l) iodide; tri-tert-butyl phosphine; potassium carbonate; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran; toluene at 120℃; for 24h; Sonogashira Cross-Coupling; Sealed tube; Inert atmosphere;	63%
With copper(l) iodide; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); triethylamine In dimethyl sulfoxide at 120℃; for 1h; Sonogashira Cross-Coupling; Microwave irradiation;	61%
With copper(l) iodide; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); triethylamine In dimethyl sulfoxide at 120℃; for 1h; Microwave irradiation;	2.15 g

(2-(6-methylpyridin-2-yl)-5,6-dihydro-4Hpyrrolo[1,2-b]pyrazol-3-yl)boronic acid (705262-42-6) + 5-bromo-7-azaindazole (875781-17-2) → 5-[2-[6-methyl-(pyridin-2-yl)]-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-1H-pyrazolo[3,4-b]pyridine

Conditions	Yield
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In water; dimethyl sulfoxide at 110℃; for 0.166667h; Microwave irradiation;	56%

5-bromo-7-azaindazole (875781-17-2) + 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole (832114-00-8) → 3,5-dimethyl-4-(1H-pyrazolo[3,4-b]pyridin-5-yl)isoxazole

Conditions	Yield
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium carbonate In water; acetonitrile at 110℃; for 0.25h; Microwave irradiation;	55%

methanol (67-56-1) + 5-bromo-7-azaindazole (875781-17-2) + carbon monoxide (201230-82-2) → 1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid methyl ester (1196156-42-9)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 100℃; for 12h;	46%
With palladium diacetate; triethylamine; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 12h;

5-bromo-7-azaindazole (875781-17-2) + [1.1.1]propellane (35634-10-7) + C21H29IO6 → C16H18BrN3O

Conditions	Yield
With tris[2-phenylpyridinato-C2,N]iridium(III); copper acetylacetonate; N,N,N′,N′-tetramethyl-N″-tert-butylguanidine In 1,4-dioxane Irradiation;	46%

5-bromo-7-azaindazole (875781-17-2) + ethyl 1-methyl-7-((trimethylsilyl)ethynyl)-1H-indole-2-carboxylate → ethyl 7-((1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)-1-methyl-1H-indole-2-carboxylate

Conditions	Yield
With copper(l) iodide; tetrabutyl ammonium fluoride; triethylamine In N,N-dimethyl-formamide Heating;	42%

5-bromo-7-azaindazole (875781-17-2) + 7-amino-3-bromo-1-cyclopentyl-5-methyl-1,6-naphthyridin-2(1H)-one (1552300-42-1) → 7-amino-1-cyclopentyl-5-methyl-3-(1H-pyrazolo[3,4-b]pyridin-5-yl)-1,6-naphthyridin-2(1H)-one (1552300-56-7)

Conditions	Yield
Stage #1: 5-bromo-7-azaindazole With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; bis(pinacol)diborane In 1,4-dioxane at 100℃; for 3h; Inert atmosphere; Stage #2: 7-amino-3-bromo-1-cyclopentyl-5-methyl-1,6-naphthyridin-2(1H)-one With potassium carbonate In 1,4-dioxane; water at 100℃; for 3h; Inert atmosphere;	28%

2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid + 5-bromo-7-azaindazole (875781-17-2) → 2-(4-(1H-pyrazolo[3,4-b]pyridin-5-yl)phenyl)acetic acid

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In water; acetonitrile at 100℃; for 3h; Inert atmosphere;	28%

5-bromo-7-azaindazole (875781-17-2) + 2-(4-morpholinyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoxaline (1083325-84-1) → 2-(4-morpholinyl)-7-(1H-pyrazolo[3,4-b]pyridin-5-yl)quinoxaline (1083320-98-2)

Conditions	Yield
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 110℃; for 18h;	26%

Upstream product

• 1820-80-0 3-aminopyrazole 
• 2065-75-0 2-Bromo-malonaldehyde 
• 1225387-53-0 3⁽⁵⁾-aminopyrazole 
• 875781-16-1 C₈H₁₀BrN₃O₂*ClH 
• 766-11-0 5-bromo-2-fluoropyridine 
• 875781-15-0 5-bromo-2-fluoro-3-pyridinecarboxaldehyde 
• 1083326-08-2 5-bromo-3-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-2(1H)-pyridinone hydrazone 

Downstream Products

• 875781-22-9 morpholin-4-yl-[3-(1H-pyrazolo[3,4-b]pyridin-5-yl)-phenyl]-methanone 
• 791-28-6 Triphenylphosphine oxide 
• 875781-18-3 5-bromo-3-iodo-1H-pyrazolo[3,4-b]pyridine 
• 1111638-35-7 5-bromo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridine 
• 1198438-24-2 5-bromo-1-(phenylsulfonyl)-1H-pyrazolo[3,4-b]pyridine 
• 1257628-77-5 3-(2-(1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide 
• 1421685-02-0 3-(2-(1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide 
• 1421685-03-1 C₃₀H₂₉F₃N₆O 
• 1421685-04-2 C₃₁H₂₉F₃N₆O 
• 1421685-05-3 C₂₈H₂₄ClF₃N₆O 
• 1421685-07-5 C₃₂H₃₁F₃N₆O 
• 1421685-06-4 C₃₀H₂₉F₃N₆O 
• 1421685-08-6 C₃₅H₃₁F₃N₆O 
• 1421783-64-3 3-((1H-pyrazolo[3,4-b]pyridin-5-yl)ethynyl)-4-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)benzamide bismethanesulfonic acid 

Relevant academic research and scientific papers

Azaindazole bipyridine derivative myeloid cell proliferation inhibitor as well as preparation method and application thereof in pharmacy

The invention provides an azaindazole bipyridine derivative myeloid cell proliferation inhibitor shown as a formula I, wherein R1, R2 and R3 have the meanings defined in the specification of the invention. A compound in formula I can significantly inhibit proliferation and related disordersof myeloid cells represented by MOLM-16, HL-60, and MV-4-11. The formula I or salt thereof or the related pharmaceutical composition provided by the invention has excellent in-vivo and in-vitro inhibitory activity, good druggability, high bioavailability and no obvious damage to organs. Therefore, the compound shown in the formula I or the salt thereof and the related drug combination have huge clinical application prospects.

Zinc Acetate-Promoted Buchwald-Hartwig Couplings of Heteroaromatic Amines

Zinc salts have been shown to promote the Buchwald-Hartwig coupling of azaindoles and azaindazoles with heteroaryl chlorides to provide the corresponding 1-aryl-1H-azaindoles and 1-aryl-1H-azaindazoles. The substrate scope and mechanistic aspects of this reaction were explored.

3-(1H-PYRROLO[3,2-C]PYRIDIN-2-YL)-1H-PYRAZOLO[3,4-B]PYRIDINES AND THERAPEUTIC USES THEREOF

7-Azaindazole compounds for treating various diseases and pathologies are disclosed. More particularly, the present disclosure concerns the use of a 7-azaindazole compound or analogs thereof, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., cancer, abnormal cellular proliferation, angiogenesis, fibrotic disorders, bone or cartilage diseases, and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, as well as genetic diseases and neurological conditions/disorders/diseases due to mutations or dysregulation of the Wnt pathway and/or of one or more of Wnt signaling components. Also provided are methods for treating Wnt-related disease states.

3-(1H-PYRROLO[2,3-C]PYRIDIN-2-YL)-1H-PYRAZOLO[3,4-B]PYRIDINES AND THERAPEUTIC USES THEREOF

7-Azaindazole compounds for treating various diseases and pathologies are disclosed. More particularly, the present disclosure concerns the use of a 7-azaindazole compound or analogs thereof, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., cancer, abnormal cellular proliferation, angiogenesis, fibrotic disorders, bone or cartilage diseases, and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, as well as genetic diseases and neurological conditions/disorders/diseases due to mutations or dysregulation of the Wnt pathway and/or of one or more of Wnt signaling components. Also provided are methods for treating Wnt-related disease states.

3-(1H-INDOL-2-YL)-1H-PYRAZOLO[3,4-B]PYRIDINES AND THERAPEUTIC USES THEREOF

7-Azaindazole compounds for treating various diseases and pathologies are disclosed. More particularly, the present disclosure concerns the use of a 7-azaindazole compound or analogs thereof, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., cancer, abnormal cellular proliferation, angiogenesis, fibrotic disorders, bone or cartilage diseases, and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, as well as genetic diseases and neurological conditions/disorders/diseases due to mutations or dysregulation of the Wnt pathway and/or of one or more of Wnt signaling components. Also provided are methods for treating Wnt-related disease states.

3-(1H-PYRROLO[2,3-B]PYRIDIN-2-YL)-1H-PYRAZOLO[3,4-B]PYRIDINES AND THERAPEUTIC USES THEREOF

7-Azaindazole compounds for treating various diseases and pathologies are disclosed. More particularly, the present disclosure concerns the use of a 7-azaindazole compound or analogs thereof, in the treatment of disorders characterized by the activation of Wnt pathway signaling (e.g., cancer, abnormal cellular proliferation, angiogenesis, fibrotic disorders, bone or cartilage diseases, and osteoarthritis), the modulation of cellular events mediated by Wnt pathway signaling, as well as genetic diseases and neurological conditions/disorders/diseases due to mutations or dysregulation of the Wnt pathway and/or of one or more of Wnt signaling components. Also provided are methods for treating Wnt-related disease states.

Synthesis of 5-cyano -1H-pyrazolo [3,4-b] pyridine method

The invention discloses a method for synthesis of 5-cyano-1H-pyrazolo[3,4-b]pyridine. The method comprises the following steps of synthesizing LDA, synthesizing an intermediate I, synthesizing an intermediate II, synthesizing a 5-cyano-1H-pyrazolo[3,4-b]pyridine finished product and carrying out follow-up purification treatment. The method utilizes cheap and easily available raw materials, greatly reduces a production cost, has a reasonable raw material ratio, simple and short processes and mild conditions, is safe and reliable, can prepare a target product having high purity and is especially suitable for industrial production.

GPR40 RECEPTOR AGONIST, METHODS OF PREPARING THE SAME, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME AS AN ACTIVE INGREDIENT

The present invention relates to a novel compound having GPR40 receptor agonist activity that promotes insulin secretion and inhibits blood sugar rise after glucose loading, and is thereby useful for the treatment of diabetes and complications thereof, the preparation method thereof and pharmaceutical composition containing them as an active ingredient.

PYRAZOLE [3, 4-B] PYRIDINE RAF INHIBITORS

Compounds of Formula I are useful for inhibition of Raf kinases. Methods of using compounds of Formula I and stereoisomers, tautomers, prodrugs and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

PYRAZOLE COMPOUNDS

The present invention is directed to compounds of Formula (I) and to pharmaceutically acceptable salts thereof, their synthesis, and their use as Raf inhibitors.