53014-84-9

Usage

Uses

Used in Pharmaceutical Industry:
3-FORMYL-6-METHYL-PYRIDINE is used as a building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs and medicinal compounds. Its unique structure allows for the creation of diverse chemical entities with potential therapeutic applications.
Used in Agricultural Chemical Industry:
In the agricultural sector, 3-FORMYL-6-METHYL-PYRIDINE is utilized as a key intermediate in the production of agricultural chemicals, aiding in the development of effective pest control agents and other agrochemicals to enhance crop protection and yield.
Used as a Flavoring Agent in Food Industry:
3-FORMYL-6-METHYL-PYRIDINE is employed as a flavoring agent in food products, imparting specific taste profiles and enhancing the overall sensory experience of various food items.
Used in Dye Production:
3-FORMYL-6-METHYL-PYRIDINE is used as an intermediate in the production of dyes, playing a crucial role in the synthesis of colorants for various applications, including textiles, plastics, and other industries.
Used in the Synthesis of Other Organic Compounds:
3-FORMYL-6-METHYL-PYRIDINE is also utilized in the synthesis of a wide range of organic compounds, showcasing its versatility and importance in organic chemistry and chemical engineering.

InChI:InChI=1/C7H7NO/c1-6-2-3-7(5-9)4-8-6/h2-5H,1H3

Synthetic route

6-methyl-3-pyridinemethanol (34107-46-5) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
Stage #1: 6-methyl-3-pyridinemethanol With oxalyl dichloride; dimethyl sulfoxide In dichloromethane at -60℃; for 1.33333h; Stage #2: With triethylamine In dichloromethane at -60 - 20℃; for 0.166667h;	85%
With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -60℃; for 1.5h;	85%
With lead(IV) acetate In toluene for 2.5h; Heating;	57%

5-bromo-2-methylpyridine (3430-13-5) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
Stage #1: 5-bromo-2-methylpyridine With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane at -10℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0℃; for 2h;	85%
Stage #1: 5-bromo-2-methylpyridine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 1h;	72%
Stage #1: 5-bromo-2-methylpyridine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78℃; for 1h;	72%
Stage #1: 5-bromo-2-methylpyridine With n-butyllithium; isopropylmagnesium chloride In tetrahydrofuran; hexane at 10℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at 20℃; for 2h;	38%
Stage #1: 5-bromo-2-methylpyridine With isopropylmagnesium chloride In tetrahydrofuran at 0 - 20℃; for 6h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at 0 - 20℃;	4.5 g

dihydroxy-methyl-borane (13061-96-6) + 6-bromonicotinaldehyde (149806-06-4) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
	16%

6-methyl-pyridine-3-carbaldehyde semicarbazone (106837-80-3) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
With hydrogenchloride; water; 3-nitro-benzaldehyde

2,5-dimethylpyridine (589-93-5) → 5-methylpicolinaldehyde (4985-92-6) + 2-methyl-5-formylpyridine (53014-84-9) + carbon oxides

Conditions	Yield
β-VO(PO3)2 In gas at 400℃; Product distribution; Rate constant; selectivity of reaction, rates of partial and total oxidation;

N-methoxy-N-methyl-6-methylnicotinamide (221615-71-0) → 2-methyl-5-formylpyridine (53014-84-9) + C5H5NCH2C(NC2H6O)2

Conditions	Yield
With diisobutylaluminium hydride In toluene at -20 - -5℃; for 0.5h;

Methyl 6-methylnicotinate (5470-70-2) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: i-PrMgCl / toluene; tetrahydrofuran / 0.5 h / -10 °C 2: DIBAL-H / toluene / 0.5 h / -20 - -5 °C View Scheme
Multi-step reaction with 2 steps 1: 75 percent / LAH / diethyl ether / 0.5 h / -78 °C 2: 1.) oxalyl chloride, dimethyl sulfoxide, 2.) triethylamine / 1.) methylene chloride, -60 deg C, 20 min, 2.) from -60 deg C to RT View Scheme
Stage #1: Methyl 6-methylnicotinate With lithium aluminium tetrahydride In tetrahydrofuran at -78℃; for 4h; Stage #2: With manganese(IV) oxide In dichloromethane for 6h; Heating / reflux;

ethyl 6-methylnicotinate (21684-59-3) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / sodium bis(2-methoxyethoxy)aluminum hydride / diethyl ether / Heating 2: 57 percent / Pb(OAc)4 / toluene / 2.5 h / Heating View Scheme
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran View Scheme
Multi-step reaction with 2 steps 1: diethyl ether; water 2: pyridine; water View Scheme

6-methylnicotinonitrile (3222-48-8) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Raney nickel; ethanol / Hydrogenation.unter Zusatz einer wss. Loesung von Semicarbazid-hydrochlorid und Natriumacetat 2: 3-nitro-benzaldehyde; hydrochloric acid; water View Scheme

2-methyl-5-vinylpyridine (140-76-1) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
With sodium periodate; osmium(VIII) oxide In 1,2-dimethoxyethane; water

N-methoxy-N-methyl-6-methylnicotinamide (221615-71-0) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
Stage #1: N-methoxy-N-methyl-6-methylnicotinamide With diisobutylaluminium hydride In hexane; dichloromethane at -10℃; for 0.166667h; Inert atmosphere; Stage #2: With water In hexane; dichloromethane at 20℃; for 1h;

6-methylnicotinic acid (3222-47-7) → 2-methyl-5-formylpyridine (53014-84-9)

Conditions	Yield
Swern Oxidation;

2-methyl-5-formylpyridine (53014-84-9) → (3E)-6-methylpyridine-3-carbaldehyde oxime

Conditions	Yield
With hydroxylamine In methanol; water at 20 - 40℃; for 23h; Inert atmosphere;	98%

2-methyl-5-formylpyridine (53014-84-9) → 6-methylnicotinaldehyde oxime (89693-75-4)

Conditions	Yield
With hydroxylamine In methanol; water at 20 - 40℃; for 4h;	94%
With hydroxylamine In methanol; water at 40℃; for 2h;	94%
With hydroxylamine hydrochloride; sodium carbonate In ethanol; water at 20℃;

2-methyl-5-formylpyridine (53014-84-9) + allylmagnesium bromide (1730-25-2) → 1-(6-methylpyridin-3-yl)but-3-en-1-ol (1566970-97-5)

Conditions	Yield
In tetrahydrofuran at -40 - -20℃; for 0.166667h;	94%

2-methyl-5-formylpyridine (53014-84-9) + (±)-3,7-dimethyloctanehydrazide → 3,7-dimethyl-N'-[(6-methylpyridin-3-yl)methylidene]octanehydrazide

Conditions	Yield
In methanol Reflux;	92%

2-methyl-5-formylpyridine (53014-84-9) + 6‑(1H‑indol‑3‑yl)‑4,5′‑bipyrimidine‑2‑amine → (E)‑N‑[6‑(1H‑indol‑3‑yl)‑4,5′‑bipyrimidine‑2‑yl]‑1‑(6‑methylpyridin‑3‑yl)methanimine

Conditions	Yield
With acetic acid In ethanol for 18h; Reflux;	90%

2-methyl-5-formylpyridine (53014-84-9) + malonic acid dimethyl ester (108-59-8) → dimethyl 2-((6-methylpyridin-3-yl)methylene)malonate

Conditions	Yield
With piperidine; acetic acid In toluene at 110℃; for 18h; Schlenk technique; Inert atmosphere; Sealed tube;	87%

2-methyl-5-formylpyridine (53014-84-9) + malonic acid (141-82-2) → 3-(6-methyl-pyridin-3-yl)-acrylic acid (117830-17-8)

Conditions	Yield
With piperidine In pyridine at 100℃;	77%

2-methyl-5-formylpyridine (53014-84-9) + uracil (66-22-8) → 5-<(6-methyl-3-pyridinyl)hydroxymethyl>-2,4(1H,3H)-pyrimidinedione (83902-97-0) + 5,5'-<(6-methyl-3-pyridinyl)methylene>bis(2,4(1H,3H)-pyrimidinedione) (102396-65-6)

Conditions	Yield
With hydrogenchloride for 8h; Heating;	A 70% B n/a

2-methyl-5-formylpyridine (53014-84-9) + ethyl 2-cyanoacetate (105-56-6) → ethyl (2E)-2-cyano-3-(6-methylpyridin-3-yl)prop-2-enoate

Conditions	Yield
With piperidine; acetic acid In ethanol at 20℃; for 16h;	70%

2-methyl-5-formylpyridine (53014-84-9) + ethyl acrylate (140-88-5) → 2-[(hydroxy)(6-methylpyridin-3-yl)methyl] acrylic acid ethyl ester (1362851-35-1)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane at 20℃;	62%

2-methyl-5-formylpyridine (53014-84-9) + malonic acid (141-82-2) → 3-amino-3-(6-methyl-3-pyridyl)propionic acid (252989-81-4)

Conditions	Yield
With ammonium acetate In ethanol for 6h; Condensation; Heating;	61%
With ammonium acetate In ethanol Reflux;

2-methyl-5-formylpyridine (53014-84-9) + N-{3-[4-amino-1-hydroxy-4-(3,3-dimethylbutyl)-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}methanesulfonamide hydrochloride (909106-48-5) → N-[3-(4-(3,3-dimethylbutyl)-1-hydroxy-4-{[(6-methylpyridin-3-yl)methyl]amino}-3-oxo-3,4-dihydronaphthalen-2-yl)-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl]methanesulfonamide

Conditions

Yield

Stage #1: N-{3-[4-amino-1-hydroxy-4-(3,3-dimethylbutyl)-3-oxo-3,4-dihydronaphthalen-2-yl]-1,1-dioxido-4H-1,2,4-benzothiadiazin-7-yl}methanesulfonamide hydrochloride With N-ethyl-N,N-diisopropylamine In 1,2-dichloro-ethane at 20℃; for 0.0833333h; Stage #2: 2-methyl-5-formylpyridine With magnesium sulfate In 1,2-dichloro-ethane at 50℃; for 18h; Stage #3: With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 18h;

58%

2-methyl-5-formylpyridine (53014-84-9) + (bromomethyl)triphenyl phosphonium bromide (1034-49-7) → 5-(2-bromovinyl)-2-methylpyridine (1189785-37-2)

Conditions	Yield
Stage #1: (bromomethyl)triphenyl phosphonium bromide With potassium tert-butylate In tetrahydrofuran at -78 - 0℃; Inert atmosphere; Stage #2: 2-methyl-5-formylpyridine In tetrahydrofuran at -78℃; for 5h;	56%

2-methyl-5-formylpyridine (53014-84-9) + 1-(7-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-2H-chromen-8-yl)ethan-1-one (54246-37-6) → (E)-1-(7-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-2H-chromen-8-yl)-3-(6-methylpyridin-3-yl)prop-2-en-1-one

Conditions	Yield
Stage #1: 1-(7-hydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)-2H-chromen-8-yl)ethan-1-one With sodium hydride In tetrahydrofuran at 0 - 20℃; Stage #2: 2-methyl-5-formylpyridine In tetrahydrofuran at 0 - 30℃;	55%

2-methyl-5-formylpyridine (53014-84-9) + 2-(furan-2-yl)cyclopropanecarbohydrazide → (E)-2-(furan-2-yl)-N'-((6-methylpyridin-3-yl)methylene)cyclopropanecarbohydrazide

Conditions	Yield
With zinc(II) oxide In ethanol at 20℃; Reagent/catalyst; Solvent; Green chemistry;	51%

2-methyl-5-formylpyridine (53014-84-9) + sodium chlorodifluoroacetate (1895-39-2) → 5-(2,2-difluorovinyl)-2-methylpyridine

Conditions	Yield
With triphenylphosphine In N,N-dimethyl-formamide at 100℃; Inert atmosphere;	46%

2-methyl-5-formylpyridine (53014-84-9) + isopropylmagnesium chloride (1068-55-9) → 1-(6-methylpyridin-3-yl)-2-methylpropan-1-ol

Conditions	Yield
With diisopropyl zinc; (2S)-(−)-3-exo-(morpholino)isoborneol In tetrahydrofuran; diethyl ether at 20℃; for 1h; Inert atmosphere; Schlenk technique;	39%
In tetrahydrofuran Inert atmosphere;

2-methyl-5-formylpyridine (53014-84-9) + 2-(4-(piperazin-1-yl)phenyl)benzo[d]oxazole (885275-02-5) → 2-(4-(4-((6-methylpyridin-3-yl)methyl)piperazin-1-yl)phenyl)benzo[d]oxazole (1426259-87-1)

Conditions	Yield
With formic acid In N,N-dimethyl-formamide at 100℃; for 3h; Inert atmosphere;	38%

2-methyl-5-formylpyridine (53014-84-9) + 4-[(4-{5-[(piperidin-4-yl)methoxy]pyridine-2-carbonyl}-piperazin-1-yl)methyl]benzonitrile → 4-({4-[5-({1-[(6-methylpyridin-3-yl)methyl]piperidin-4-yl}methoxy)pyridine-2-carbonyl]piperazin-1-yl}methyl)-benzonitrile tetrahydrochloride

Conditions	Yield
Stage #1: 2-methyl-5-formylpyridine; 4-[(4-{5-[(piperidin-4-yl)methoxy]pyridine-2-carbonyl}-piperazin-1-yl)methyl]benzonitrile With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; Stage #2: With hydrogenchloride In 1,4-dioxane; methanol	38%

2-methyl-5-formylpyridine (53014-84-9) + (Z)-5-((2-(4-(aminomethyl)piperidin-1-yl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione (1312662-54-6) + trifluoroacetic acid (76-05-1) → (Z)-5-((2-(4-((((6-methylpyridin-3-yl)methyl)amino)methyl)piperidin-1-yl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione trifluoroacetate

Conditions

Yield

Stage #1: 2-methyl-5-formylpyridine; (Z)-5-((2-(4-(aminomethyl)piperidin-1-yl)pyrimidin-4-yl)methylene)thiazolidine-2,4-dione With N-ethyl-N,N-diisopropylamine In cis-1,2-Dichloroethylene; N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In cis-1,2-Dichloroethylene; N,N-dimethyl-formamide at 20℃; for 16h; Stage #3: trifluoroacetic acid In cis-1,2-Dichloroethylene for 24h;

37.2%

2-methyl-5-formylpyridine (53014-84-9) + C27H31N7O3 → C29H30N8O

Conditions	Yield
Stage #1: C27H31N7O3 With trifluoroacetic acid In dichloromethane at 20℃; for 3h; Stage #2: 2-methyl-5-formylpyridine With acetic acid at 20℃; for 0.5h; Stage #3: With sodium tris(acetoxy)borohydride at 20℃;	36%

2-methyl-5-formylpyridine (53014-84-9) + 2-{[4-tert-butyl-5-(1H-1,2,4-triazol-1-yl)-1,3-thiazol-2-yl]imino}-1,3-thiazolidin-4-one → 2-{(4-tert-butyl-5-(1H-1,2,4-triazol-1-yl)thiazole-2-yl)imino}-5-[(6-methylpyridin-3-yl)methylidene]-4-thiazolidinone

Conditions	Yield
With sodium acetate; acetic acid for 10h; Reflux;	33%

2-methyl-5-formylpyridine (53014-84-9) + 4,5-diamino-6-chloro-N4-methylpyrimidine (52602-68-3) → 6-chloro-9-methyl-8-(6-methylpyridin-3-yl)-9H-purine

Conditions	Yield
With iron(III) chloride hexahydrate In N,N-dimethyl-formamide at 90℃; for 16h;	33%

2-methyl-5-formylpyridine (53014-84-9) + diethylamine (109-89-7) → N-ethyl-N-((6-methylpyridin-3-yl)methyl)ethanamine

Conditions	Yield
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 16h;	31%

2-methyl-5-formylpyridine (53014-84-9) + (-)-2-((3,4-trans)-4-methylpyrrolidin-3-yl)-7-(tetrahydro-2H-pyran-4-yl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one → (+)-2-((3,4-trans)-4-methyl-1-((6-methylpyridin-3-yl)methyl)pyrrolidin-3-yl)-7-(tetrahydro-2H-pyran-4-yl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one

Conditions	Yield
Stage #1: 2-methyl-5-formylpyridine; (-)-2-((3,4-trans)-4-methylpyrrolidin-3-yl)-7-(tetrahydro-2H-pyran-4-yl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one With methanol at 20℃; for 2h; Inert atmosphere; Stage #2: With sodium cyanoborohydride at 20℃; for 8h; Inert atmosphere;	21%

2-methyl-5-formylpyridine (53014-84-9) + 2-amino-N-(4-(methylthio)phenyl)benzamide → 2-(6-methylpyridin-3-yl)-3-(4-(methylthio)phenyl)quinazolin-4(3H)-one (1235480-42-8)

Conditions	Yield
With copper dichloride In ethanol for 6h; Reflux;	19%

2-methyl-5-formylpyridine (53014-84-9) + 2-amino-N-(4-cyclopropylphenyl)benzamide (1235480-97-3) → 3-(4-cyclopropylphenyl)-2-(6-methylpyridin-3-yl)quinazolin-4(3H)-one (1235480-46-2)

Conditions	Yield
With copper dichloride In ethanol for 2.5h; Reflux;	15%

Upstream product

• 106837-80-3 6-methyl-pyridine-3-carbaldehyde semicarbazone 
• 34107-46-5 6-methyl-3-pyridinemethanol 
• 589-93-5 2,5-dimethylpyridine 
• 221615-71-0 N-methoxy-N-methyl-6-methylnicotinamide 
• 3430-13-5 5-bromo-2-methylpyridine 
• 68-12-2 N,N-dimethyl-formamide 
• 13061-96-6 dihydroxy-methyl-borane 
• 149806-06-4 6-bromonicotinaldehyde 
• 5470-70-2 Methyl 6-methylnicotinate 
• 21684-59-3 ethyl 6-methylnicotinate 
• 3222-48-8 6-methylnicotinonitrile 
• 140-76-1 2-methyl-5-vinylpyridine 
• 3222-47-7 6-methylnicotinic acid 

Downstream Products

• 159295-41-7 diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(Z)-2-(6-methylpyridin-3-yl)vinyl]-3-cephem-4-carboxylate 
• 265113-58-4 5-(6-Methyl-3-pyridyl)-1-(4-methylsulfonylphenyl)imidazole(73 % yield) 
• 202409-33-4 etoricoxib 
• 221615-75-4 1-(6-methyl-3-pyridinyl)-2-[4-(methylsulfonyl)phenyl]ethanone 
• 307531-87-9 1-(6-methyl-3-pyridinyl)-1-(aminophenyl)methanodiphenylphosphonic acid 
• 118420-47-6 N-[3-(6-methyl-pyridin-3-yl)acryloyl]-4-(4-diphenylmethyl-1-piperazinyl)butylamine 
• 117830-04-3 (E)-N-[4-(4-Benzhydrylidene-piperidin-1-yl)-butyl]-3-(6-methyl-pyridin-3-yl)-acrylamide 
• 118420-58-9 (2E,4E)-5-(6-Methyl-pyridin-3-yl)-penta-2,4-dienoic acid [3-(4-benzhydryl-piperazin-1-yl)-propyl]-amide 
• 118420-59-0 (2E,4E)-5-(6-Methyl-pyridin-3-yl)-penta-2,4-dienoic acid [4-(4-benzhydryl-piperazin-1-yl)-butyl]-amide 
• 107755-61-3 (E)-N-[4-(4-Benzhydryl-piperazin-1-yl)-butyl]-2-methyl-3-(6-methyl-pyridin-3-yl)-acrylamide 
• 107755-79-3 N-[3-(6-methyl-pyridin-3-yl)propionyl]-4-(4-diphenylmethyl-1-piperazinyl)butylamine 
• 118420-31-8 (E)-3-(6-Methyl-pyridin-3-yl)-N-{4-[4-(phenyl-p-tolyl-methyl)-piperazin-1-yl]-butyl}-acrylamide 
• 72716-93-9 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)-4(1H)-pyrimidone 
• 71351-48-9 3-(6-methyl-pyridin-3-yl)-propionic acid ethyl ester 

Relevant academic research and scientific papers

Bromine-magnesium exchange of 5-bromo-2-picoline via an organomagnesium complex nBu2iPrMgLi: A new preparation methodology of functionalized picolines under noncryogenic conditions

The organomagnesium complex nBu2iPrMgLi, readily prepared from nBuLi and iPrMgCl (2:1), is quite efficient for the bromine-magnesium exchange of 5-bromo-2-picoline under noncryogenic conditions (at -10°C). The resulting picolylmagnesium complex reacts with various electrophiles to afford functionalized picolines.

2,6-DIOXO,-2,3-DIHYDRO-1H-PURINE COMPOUNDS USEFUL FOR TREATING DISORDERS RELATED TO THE ACTIVITY OF THE TRPA1 CHANNEL

Compounds of formula (VIII) and compositions for treating disorders related to TRPA1 are described herein.

2 - methyl - 5 - vinyl pyridine synthesis method (by machine translation)

The invention discloses a 2 - methyl - 5 - vinyl pyridine synthesis method, for the purpose of, reduce the synthesis step, to simplify the processing process, and improving the yield and save the cost, reducing chemical raw material consumption, effective protection of the environment, the use of the technical proposal is: (1) the raw material 6 - methyl nicotinic acid methyl ester is reduced to the 2 - methyl - 5 - pyridine base formaldehyde; (2) preparing the phosphorus ylide reagent; (3) the 2 - methyl - 5 - pyridyl formaldehyde and phosphorus ylide reagent in the reaction of 2 - methyl - 5 - vinyl pyridine, concentrated rectification to obtain the product. (by machine translation)

PYRAZOLOPYRIMIDINES AS INHIBITORS OF GLUCOCORTICOID RECEPTOR TRANSLOCATION

Provided herein are compounds and pharmaceutical compositions comprising said compounds. The subject compounds and compositions are useful as modulators of Glucocorticoid Receptor (GR) translocation. Furthermore, the subject compounds and compositions are useful for the treatment of diseases involved in the hypothalamic-pituitary-adrenal (HPA) axis.

KYNURENINE PRODUCTION INHIBITOR

Provided is a kynurenine production inhibitor comprising a nitrogen-containing heterocyclic compound represented by formula (I): (wherein R50 and R51 may be the same or different and each represent a hydrogen atom or the like, G1 and G2 may be the same or different and each represent a nitrogen atom or the like, X represents formula (III): (wherein m1 and m2 may be the same or different and each represent an integer of 0 or 1, Y represents an oxygen atom or the like, and R6 and R7 may be the same or different and each represent a hydrogen atom or the like), R1 represents optionally substituted lower alkyl or the like, R2 represents a hydrogen atom or the like, and R3 represents optionally substituted lower alkyl or the like), and the like.

BENZIMIDAZOLES AND RELATED ANALOGS AS SIRTUIN MODULATORS

Provided herein are sirtuin-modulating compounds of formula (II) The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

PYRIDOINDOLE MODULATORS OF NMDA RECEPTOR AND ACETYLCHOLINESTERASE

The present invention relates to new pyridoindole modulators of NMDA receptors, AMPA receptors, and/or L-type calcium channels, and/or inhibitors of acetylcholinesterase, pharmaceutical compositions thereof, and methods of use thereof.

IMIDAZOPYRIDINE AND RELATED ANALOGS AS SIRTUIN MODULATORS

Provided herein are novel sirtuin-modulating compounds and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

TRPA1 ANTAGONISTS

Compounds of formula (I), wherein R1, R2, R3, and Y are defined in the description are TRPA1 antagonists. Compositions comprising such compounds and methods for treating conditions and disorders using such compounds and compositions are also disclosed.

AMIDE COMPOUNDS, COMPOSITIONS AND USES THEREOF

Compounds are provided according to formula (1 ) : where A, B, W, X', L, R1, R3, R4b, and m' are as defined herein. Provided compounds and pharmaceutical compositions thereof are useful for the prevention and treatment of a variety of conditions in mammals including humans, including by way of non-limiting example, pain, inflammation, cognitive disorders, anxiety, depression, and others.