54-96-6

Basic information

• Product Name: 3,4-Diaminopyridine
• Synonyms: 3,4-diamino-pyridin;3,4-pyridinediamine;4,5-diaminopyridine;diamino-3,4pyridine;TIMTEC-BB SBB004341;PYRIDINE-3,4-DIAMINE;DIAMINOPYRIDINE(3,4-);ASINEX-REAG BAS 01447204
• CAS NO: 54-96-6
• Molecular Formula: C₅H₇N₃
• Molecular Weight: 109.13
• EINECS: 200-220-9
• Product Categories: Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;Amines;Pyridines;Boronic Acid;pyridine series;Building Blocks;C5;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 54-96-6.mol

Chemical Properties

• Melting Point: 216-218 °C(lit.)
• Boiling Point: 194.6°C (rough estimate)
• Flash Point: 240 °C
• Appearance: Brownish to brown-gray/Crystalline Powder
• Density: 1.1118 (rough estimate)
• Vapor Pressure: 1.2E-05mmHg at 25°C
• Refractive Index: 1.5340 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: 30g/l
• PKA: 9.17±0.12(Predicted)
• Water Solubility: 24 g/L (20 ºC)
• Merck: 14,2986
• BRN: 110232
• CAS DataBase Reference: 3,4-Diaminopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-Diaminopyridine(54-96-6)
• EPA Substance Registry System: 3,4-Diaminopyridine(54-96-6)

Safety Data

• Hazard Codes: T+,T,Xi
• Statements: 25-26-36/37/38
• Safety Statements: 26-28-36/37/39-45-37/39-28A-36
• RIDADR: UN 2811 6.1/PG 2
• WGK Germany: 3
• RTECS: US7600000
• F: 10-23
• HazardClass: 6.1
• PackingGroup: I
• Hazardous Substances Data: 54-96-6(Hazardous Substances Data)

Usage

Uses

Used in Neuromuscular Disorders:
3,4-Diaminopyridine is used as a treatment for Lambert-Eaton myasthenic syndrome (LEMS) and some congenital myasthenic syndromes (CMS). It functions as a potassium channel blocker in nerve terminals, inhibiting potassium channel efflux and increasing the duration of the action potential. This results in an extended opening of calcium channels and enhanced acetylcholine (ACh) release, which in turn improves muscle strength and allows muscles to contract more effectively.
Used in Autoimmune Disorders:
3,4-Diaminopyridine is used as a therapeutic agent for LEMS, an autoimmune disorder characterized by impaired neuromuscular transmission. It has been available as a treatment for LEMS in special treatment programs for approximately 25 years, providing relief and improved quality of life for patients suffering from this condition.

Mechanism of action

Amifampridine works by blocking potassium channel efflux in nerve terminals so that action potential duration is increased. Ca2+ channels can then be open for a longer time and allow greater acetylcholine release to stimulate muscle at the end plate.

Pharmacokinetics

Administration of amifampridine to patients with LES in clinical trials resulted in improvement of the compound muscle action potential (CMAP), muscle function, and quantitative myasthenia gravis (QMG) score . One case of a slight prolongation of the QTc interval in male patient with LEMS and euthyroid Hashimoto’s disease treated with 90 mg of amifampridine in combination with 100 mg azathioprine was reported . In vitro, amifampridine was shown to modulate cardiac conduction and induce phasic contractions in different arteries from several species. In addition, it stimulated potassium-evoked dopamine and noradrenaline release in rat hippocampal slices and upregulate acetylcholine release in the brain. It may also potentiate adrenergic and cholinergic neuromuscular transmission in the gatrointestinal tract. In a single pharmacokinetic study, no effect was observed of amifampridine phosphate on cardiac repolarization as assessed using the QTc interval . There were no changes in heart rate, atrioventricular conduction or cardiac depolarization as measured by the heart rate, PR and QRS interval durations.

Toxicty

The approximate oral LD50 was >25mg/kg in rats and 100 mg/kg in mice. The approximate intravenous LD50 was 25 mg/kg in both rats and mice. Peritoneal and subcutaneous LD50 in mice were 20 mg/kg and 35 mg/kg, respectively. There is limited clinical experienced with amifampridine overdose. The manifestations of acute drug overdose may include abdominal pain, and should be responded with discontinuation of treatment and initiation of supportive care with close monitoring of viral signs. There is no specific antidote known for amifampridine .

Indications

3,4-diaminopyridine has been used to treat Lambert Eaton myasthenia (LEM) for thirty years despite the lack of conclusive evidence of efficacy. Lambert–Eaton myasthenic syndrome is characterized by muscle weakness, hyporeflexia, and autonomic dysfunction, which result from impaired release of acetylcholine from cholinergic nerve terminals. It is frequently associated with cancer, it is autoimmune-mediated, and treatment has been unsatisfactory. The drug 3,4-diaminopyridine (3,4-DAP) increases neurotransmitter release and also the action potential (by blocking potassium conductance); these actions lead to a nonspecific excitatory effect on the cholinergic system, and provide benefit. It should be taken orally, 4-5 times per day. Adverse effects due to CNS excitation (insomnia, seizures) can occur.

Purification Methods

It crystallises from *benzene and is stored under N2 because it is deliquescent and absorbs CO2. [Beilstein 22/11 V 266.]

InChI:InChI=1/C5H7N3/c6-4-1-2-8-3-5(4)7/h1-3H,7H2,(H2,6,8)/p+1

Synthetic route

4-amino-3-nitropyridine (1681-37-4) → 3,4-diaminopyridine (54-96-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃; under 5250.42 Torr; for 20h; Hydrogenation;	98%
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 10℃; under 760.051 Torr; for 24h;	97%
With palladium on activated charcoal; hydrogen In tetrahydrofuran; methanol at 20℃;	97%

3-nitro-4-hydrazinopyridine (33544-42-2) → 3,4-diaminopyridine (54-96-6)

Conditions	Yield
With hydrogen; nickel In ethanol at 20 - 50℃; under 3102.9 Torr; for 2h;	94%

4-(benzylamino)-3-nitropyridine (100306-70-5) → 3,4-diaminopyridine (54-96-6)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol at 80℃; under 3102.9 Torr; for 30h;	76%

4-aminopyridine (504-24-5) + 6-(2,6-dichlorophenyl)-2-methanesulfinyl(or sulfonyl)-8-methyl-8H-pyrido<2,3-d>pyrimidin-7-one → 3,4-diaminopyridine (54-96-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 97 percent / Et3N / acetonitrile / 1 h / 20 °C 2: 72 percent / N2O5 / nitromethane / 0.17 h / 0 °C 3: 96 percent / 2 M aq. HCl / 5 h / 70 °C 4: 98 percent / H2 / 5 percent Pd/C / methanol / 20 h / 20 °C / 5250.42 Torr View Scheme

4-acetylaminopyridine (5221-42-1) → 3,4-diaminopyridine (54-96-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / N2O5 / nitromethane / 0.17 h / 0 °C 2: 96 percent / 2 M aq. HCl / 5 h / 70 °C 3: 98 percent / H2 / 5 percent Pd/C / methanol / 20 h / 20 °C / 5250.42 Torr View Scheme

N-(3-nitropyridin-4-yl)acetamide (79371-42-9) → 3,4-diaminopyridine (54-96-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 96 percent / 2 M aq. HCl / 5 h / 70 °C 2: 98 percent / H2 / 5 percent Pd/C / methanol / 20 h / 20 °C / 5250.42 Torr View Scheme

pyridin-4-ol (626-64-2) → 3,4-diaminopyridine (54-96-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: 70 percent / fuming HNO3, fuming H2SO4 / 1,2-dichloro-ethane / 7 h / 80 - 82 °C 2: PCl5 / 1) PCl5, 1,2-dichloroethane, reflux, 6 h , 2) reflux, 1 h 3: 90 percent / N2H4 / acetonitrile / 5 h / Heating 4: 94 percent / H2 / Raney Ni / ethanol / 2 h / 20 - 50 °C / 3102.9 Torr View Scheme
Multi-step reaction with 4 steps 1: 70 percent / fuming HNO3, fuming H2SO4 / 1,2-dichloro-ethane / 7 h / 80 - 82 °C 2: PCl5 / 1) PCl5, 1,2-dichloroethane, reflux, 6 h , 2) reflux, 1 h 3: 87 percent / CH3COONH4 / H2O / 7 h / Heating 4: 85 percent / H2 / 5percent Pd/C / methanol / 1.5 h / 20 - 30 °C / 2585.7 Torr View Scheme
Multi-step reaction with 4 steps 1: 70 percent / fuming HNO3, fuming H2SO4 / 1,2-dichloro-ethane / 7 h / 80 - 82 °C 2: PCl5 / 1) PCl5, 1,2-dichloroethane, reflux, 6 h , 2) reflux, 1 h 3: 163 g / ethanol / 18 h / Heating 4: 76 percent / H2 / 5percent Pd/C / ethanol / 30 h / 80 °C / 3102.9 Torr View Scheme

4-ethoxy-3-nitropyridine hydrochloride (94602-04-7) → 3,4-diaminopyridine (54-96-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 90 percent / N2H4 / acetonitrile / 5 h / Heating 2: 94 percent / H2 / Raney Ni / ethanol / 2 h / 20 - 50 °C / 3102.9 Torr View Scheme
Multi-step reaction with 2 steps 1: 87 percent / CH3COONH4 / H2O / 7 h / Heating 2: 85 percent / H2 / 5percent Pd/C / methanol / 1.5 h / 20 - 30 °C / 2585.7 Torr View Scheme
Multi-step reaction with 2 steps 1: 163 g / ethanol / 18 h / Heating 2: 76 percent / H2 / 5percent Pd/C / ethanol / 30 h / 80 °C / 3102.9 Torr View Scheme

4-hydroxy-3-nitropyridine (5435-54-1) → 3,4-diaminopyridine (54-96-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: PCl5 / 1) PCl5, 1,2-dichloroethane, reflux, 6 h , 2) reflux, 1 h 2: 90 percent / N2H4 / acetonitrile / 5 h / Heating 3: 94 percent / H2 / Raney Ni / ethanol / 2 h / 20 - 50 °C / 3102.9 Torr View Scheme
Multi-step reaction with 3 steps 1: PCl5 / 1) PCl5, 1,2-dichloroethane, reflux, 6 h , 2) reflux, 1 h 2: 87 percent / CH3COONH4 / H2O / 7 h / Heating 3: 85 percent / H2 / 5percent Pd/C / methanol / 1.5 h / 20 - 30 °C / 2585.7 Torr View Scheme
Multi-step reaction with 3 steps 1: PCl5 / 1) PCl5, 1,2-dichloroethane, reflux, 6 h , 2) reflux, 1 h 2: 163 g / ethanol / 18 h / Heating 3: 76 percent / H2 / 5percent Pd/C / ethanol / 30 h / 80 °C / 3102.9 Torr View Scheme

4-aminopyridine (504-24-5) → 3,4-diaminopyridine (54-96-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid; potassium nitrate / 6.5 h / 10 - 65 °C 2: sodium sulfide / methanol; water / 0 - 65 °C View Scheme

3,4-diaminopyridine (54-96-6) + Glyoxal (131543-46-9) → pyrido[3,4-b]pyrazine (254-86-4)

Conditions	Yield
In ethanol; water at 110℃; for 1h; Inert atmosphere; Microwave irradiation;	100%
In ethanol for 12h; Reflux;	100%
In water for 12h; Reflux;	100%

3,4-diaminopyridine (54-96-6) + di-tert-butyl dicarbonate (24424-99-5) → (3-Amino-pyridin-4-yl)-carbamic acid tert-butyl ester (183311-28-6)

Conditions	Yield
In tetrahydrofuran	100%
Stage #1: 3,4-diaminopyridine; di-tert-butyl dicarbonate In dichloromethane at 20℃; Stage #2: With potassium carbonate In dichloromethane regioselective reaction;	78%
In dichloromethane at 20℃;	78%
In dichloromethane at 20℃;	75%
With sodium chloride; potassium carbonate In tetrahydrofuran; water; ethyl acetate	950 mg (53%)

3,4-diaminopyridine (54-96-6) + 9-fluorenone-4-carbonyl chloride (7071-83-2) → C19H11N3O (915138-72-6)

Conditions	Yield
Stage #1: 3,4-diaminopyridine; 9-fluorenone-4-carbonyl chloride With triethylamine In dichloromethane for 4h; Stage #2: With hydrogenchloride; trifluoroacetic acid; trifluoroacetic anhydride at 109℃; for 0.333333h; Microwave irradiation;	100%

3,4-diaminopyridine (54-96-6) → C5H7N3*(x)H3O4P

Conditions	Yield
With phosphoric acid In ethanol at 22 - 60.4℃; for 17.5333h; Temperature; Solvent;	99.7%

carbon disulfide (75-15-0) + 3,4-diaminopyridine (54-96-6) → 1H-imidazo[4,5-c]pyridine-2(3H)-thione (7239-81-8)

Conditions	Yield
In pyridine for 5h; Heating;	99%
With potassium hydroxide In water at 70℃;

3,4-diaminopyridine (54-96-6) + Dimethyl N-(4-chloro-2-benzothiazolyl)-dithiocarbonimidate (83431-63-4) → (4-Chloro-benzothiazol-2-yl)-(1H-imidazo[4,5-c]pyridin-2-yl)-amine (103588-29-0)

Conditions	Yield
In various solvent(s) Heating;	98%

3,4-diaminopyridine (54-96-6) + carbon monoxide (201230-82-2) → 1,3-dihydro-2H-imidazo[4,5-c]pyridin-2-one (7397-68-4)

Conditions	Yield
With selenium In tetrahydrofuran at 100℃; under 22800.7 Torr; for 20h;	98%
With selenium 1.) THF, 31 kg/cm2, 100 degC, 20 h, 2.) 25 degC, 1 h;	96%

3,4-diaminopyridine (54-96-6) + benzil (134-81-6) → 2,3-diphenylpyrido<3,4-b>pyrazine (67899-59-6)

Conditions	Yield
With zirconium oxide salicylaldehyde-(3-aminopropyl)trimethoxysilane imine complex modified SBA-15 In water for 3h; Reflux;	98%
With Cu(II)-Schiff base/SBA-15 In water for 2h; Reflux;	97%
With SBA-15 mesoporous silica supported Fe(III)-Schiff base In water for 2h; Reflux;	96%

3,4-diaminopyridine (54-96-6) + acetyllithocholic acid (4057-84-5) → 3α-(O-acetyllithocholoyloxy)-23-(1H-imidazo(4,5-c)pyridin-2-yl)norcholane

Conditions	Yield
With boric acid In xylene for 480h; Heating;	98%

3,4-diaminopyridine (54-96-6) + trifluoroacetic acid (76-05-1) → 2-Trifluoromethyl-3H-imidazo<4,5-c>pyridine (19918-36-6)

Conditions	Yield
for 48h; Heating;	98%

3,4-diaminopyridine (54-96-6) + Thiazole-4-carboxylic acid (3973-08-8) → 4-(1H-imidazo[4,5-c]pyridin-2-yl)thiazole (65911-26-4)

Conditions	Yield
With PPA at 180℃; for 2h;	98%

3,4-diaminopyridine (54-96-6) → 1,4-dihydro-pyrido[3,4-b]pyrazine-2,3-dione (35251-84-4)

Conditions	Yield
With oxalic acid In hydrogenchloride	98%

3,4-diaminopyridine (54-96-6) + 1,2-bis(4-fluorophenyl)ethane-1,2-dione (579-39-5) → 2,3-bis(4-fluorophenyl)pyrido[3,4-b]pyrazine (309970-10-3)

Conditions	Yield
With Cu(II)-Schiff base/SBA-15 In water for 2h; Reflux;	98%
With zirconium oxide salicylaldehyde-(3-aminopropyl)trimethoxysilane imine complex modified SBA-15 In water for 2h; Reflux;	97%
With SBA-15 mesoporous silica supported Fe(III)-Schiff base In water for 2h; Reflux;	95%
With ziconium(IV) oxychloride octahydrate In water at 100℃; for 2.5h; Green chemistry;	88%
With mesoporous silica SBA-15 functionalized with Cu(II)-DiAmSar complex In neat (no solvent) at 100℃; for 0.833333h;	78%

3,4-diaminopyridine (54-96-6) + acenaphthene quinone (82-86-0) → acenaphtho[1,2-b]pyrido[3,4-e]pyrazine (22724-35-2)

Conditions	Yield
With zirconium oxide salicylaldehyde-(3-aminopropyl)trimethoxysilane imine complex modified SBA-15 In water for 2h; Reflux;	98%
With Cu(II)-Schiff base/SBA-15 In water for 2h; Reflux;	96%
With SBA-15 mesoporous silica supported Fe(III)-Schiff base In water for 2h; Reflux;	96%
With ziconium(IV) oxychloride octahydrate In water at 100℃; for 2.5h; Green chemistry;	86%
With mesoporous silica SBA-15 functionalized with Cu(II)-DiAmSar complex In neat (no solvent) at 100℃; for 0.833333h;	80%

3,4-diaminopyridine (54-96-6) + 9,10-phenanthrenequinone (84-11-7) → dibenzo[f,h]pyrido[3,4-b]quinoxaline (215-65-6)

Conditions	Yield
With zirconium oxide salicylaldehyde-(3-aminopropyl)trimethoxysilane imine complex modified SBA-15 In water for 2h; Reflux;	98%
With SBA-15 mesoporous silica supported Fe(III)-Schiff base In water for 2h; Reflux;	97%
In ethanol for 6h; Reflux; Inert atmosphere;	95%
With ziconium(IV) oxychloride octahydrate In water at 100℃; for 2.5h; Green chemistry;	87%
With mesoporous silica SBA-15 functionalized with Cu(II)-DiAmSar complex In neat (no solvent) at 100℃; for 0.833333h;	80%

3,4-diaminopyridine (54-96-6) + methyl 2,2,2-trichloroacetimidate (2533-69-9) → N-(3-aminopyridin-4-yl)-2,2,2-trichloroacetamide (1448536-56-8)

Conditions	Yield
With trifluoroacetic acid at 0 - 25℃; for 48h;	98%

3,4-diaminopyridine (54-96-6) + formic acid (64-18-6) → Imidazo<4,5-c>pyridin (272-97-9)

Conditions	Yield
at 140℃; for 48h;	97%
Heating;	87%
for 12h; Reflux;	48%

3,4-diaminopyridine (54-96-6) + S,S-Dimethyl N-(2-benzothiazolyl)-carbonimidodithioate (76423-99-9) → 2-(2-benzothiazolylamino)-imidazo<4,5-c>pyridine (103588-27-8)

Conditions	Yield
In various solvent(s) Heating;	97%

3,4-diaminopyridine (54-96-6) + valeric acid (109-52-4) → 2-n-butyl-imidazo<4,5-c>pyridine (133239-95-9)

Conditions	Yield
With PPA at 160℃; for 3h;	97%

3,4-diaminopyridine (54-96-6) + 1,2-bis(4-methoxyphenyl)-1,2-ethanedione (1226-42-2) → 2,3-bis(p-methoxyphenyl)pyrido<3,4-b>pyrazine

Conditions	Yield
With zirconium oxide salicylaldehyde-(3-aminopropyl)trimethoxysilane imine complex modified SBA-15 In water for 5h; Reflux;	97%
With SBA-15 mesoporous silica supported Fe(III)-Schiff base In water for 2h; Reflux;	95%
With Cu(II)-Schiff base/SBA-15 In water for 2h; Reflux;	94%

3,4-diaminopyridine (54-96-6) + 9,10-phenanthrenequinone (84-11-7) → dibenzo[f,h]pyrido[2,3-b]quinoxaline (215-66-7)

Conditions	Yield
With Cu(II)-Schiff base/SBA-15 In water for 2h; Reflux;	97%

3,4-diaminopyridine (54-96-6) + benzoic acid (65-85-0) → 2-phenyl-3H-imidazo[4,5-c]pyridine (75007-92-0)

Conditions	Yield
With PPA at 190℃; for 3h;	96%
With PPA; Polyphosphoric acid (PPA) at 200℃; for 3.5h;	84%
With polyphosphoric acid at 190℃; for 5h;

3,4-diaminopyridine (54-96-6) + benzoic acid (65-85-0) → 2-Phenyl-1H-imidazo<4,5-c>pyridine (75007-92-0)

Conditions	Yield
With PPA at 190℃; for 3h;	96%
With PPA at 180℃; for 3.5h;	90%
With polyphosphoric acid at 190℃; for 5h;

3,4-diaminopyridine (54-96-6) + o-fluoro-benzoic acid (445-29-4) → 2-(2-fluorophenyl)-1H-imidazo[4,5-c]pyridine

Conditions	Yield
With polyphosphoric acid at 150℃; for 18h;	96%
With PPA at 190℃; for 4h;

3,4-diaminopyridine (54-96-6) + trifluoroacetic anhydride (407-25-0) → N,N'-3,4-pyridinediylbis(2,2,2-trifluoroacetamide) trifluoroacetic acid

Conditions	Yield
In dichloromethane at 20 - 35℃; Sonication;	96%

3,4-diaminopyridine (54-96-6) + benzyl bromide (100-39-0) → 1-benzyl-4-imino-1,4-dihydropyridin-3-amine hydrobromide

Conditions	Yield
In acetonitrile at 20℃; Large scale;	96%
In acetonitrile at 15 - 25℃; Large scale;	96%

3,4-diaminopyridine (54-96-6) + 4-iodobenzoic acid (619-58-9) → C12H8IN3

Conditions	Yield
With polyphosphoric acid at 130℃; for 16h;	95.1%

3,4-diaminopyridine (54-96-6) + 4-chlorobenzaldehyde (104-88-1) → (E)-N(3)-(4-chlorobenzylidene)pyridine-3,4-diamine (1094703-76-0)

Conditions	Yield
In ethanol for 3h; Reflux; regioselective reaction;	95%

3,4-diaminopyridine (54-96-6) + 4-nitrobenzaldehdye (555-16-8) → (E)-N(3)-(4-nitrobenzylidene)pyridine-3,4-diamine (1094703-82-8)

Conditions	Yield
In ethanol for 3h; Reflux; regioselective reaction;	95%

Upstream product

• 504-24-5 4-aminopyridine 
• 5435-54-1 4-hydroxy-3-nitropyridine 
• 94602-04-7 4-ethoxy-3-nitropyridine hydrochloride 
• 626-64-2 pyridin-4-ol 
• 79371-42-9 N-(3-nitropyridin-4-yl)acetamide 
• 5221-42-1 4-acetylaminopyridine 
• 100306-70-5 4-(benzylamino)-3-nitropyridine 
• 33544-42-2 4-hydrazino-3-nitropyridine 
• 1681-37-4 4-amino-3-nitropyridine 

Downstream Products

• 79754-69-1 2-(3-Pyridyl)-1H-imidazo<4,5-c>pyridine 
• 89075-48-9 4-(3H-imidazo[4,5-c]pyridin-2-yl)benzonitrile 
• 35251-84-4 1,4-dihydro-pyrido[3,4-b]pyrazine-2,3-dione 
• 174320-64-0 3-(2-acetamidophenyl)-1H-pyrido<4,3-e>pyrazin-2-one 
• 174320-63-9 3-(2-acetamidophenyl)-1H-pyrido<3,4-e>pyrazin-2-one 
• 146097-60-1 4'-(2-n-butyl-5H-imidazo<4,5-c>pyridin-5-ylmethyl)biphenyl-2-carbonitrile 
• 133705-04-1 4'-(2-n-butyl-1H-imidazo<4,5-c>pyridin-1-ylmethyl)biphenyl-2-carbonitrile 
• 133705-03-0 4'-(2-n-butyl-3H-imidazo<4,5-c>pyridin-3-ylmethyl)biphenyl-2-carbonitrile 
• 146097-61-2 2-n-butyl-5-<2'-(1H-tetrazol-5-yl)-4-biphenylylmethyl>-5H-imidazo<4,5-c>pyridine 
• 133732-32-8 2-n-butyl-3-<2'-(1H-tetrazol-5-yl)-4-biphenylylmethyl>-3H-imidazo<4,5-c>pyridine 
• 133705-05-2 2-n-butyl-1-<2'-(1H-tetrazol-5-yl)-4-biphenylylmethyl>-1H-imidazo<4,5-c>pyridine 

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The present invention relates to novel salt of 3,4-diaminopyridine as 3,4-diaminopyridine dihydrochloride (or Amifampridine dihydrochloride), useful in the preparation of pharmaceutical composition thereof. The present application also relates to an improved process for the preparation of substantially pure Amifampridine dihydrochloride (I) having purity of greater than 99.5% (by HPLC).

Benzo[1,2-b:4,5-b′]dithiophene-Pyrido[3,4-b]pyrazine Small-Molecule Donors for Bulk Heterojunction Solar Cells

We report on the synthesis, material properties, and bulk heterojunction (BHJ) solar cell characteristics of a set of π-conjugated small-molecule (SM) donors composed of benzo[1,2-b:4,5-b′]dithiophene (BDT) and pyrido[3,4-b]pyrazine (PP) units, examining the perspectives of alkyl-substituted PP acceptor motifs in SM designs. In these systems (SM1-4), both the type of side chains derived from the PP motifs and the presence of ring substituents on BDT critically impact (i) molecular packing, and (ii) thin-film morphologies and charge transport in BHJ solar cells. With the appropriate side-chain pattern, the ring-substituted analogue SM4 stands out, achieving efficiencies of ca. 6.5% with PC71BM, and fine-scale morphologies comparable to those obtained with some of the best-performing polymer donors in BHJ solar cells. 1H-1H DQ-SQ NMR analyses are used to examine the distinct self-assembly pattern of SM4, expected to factor into the development of the BHJ morphology.

QUINOXALINONES AND DIHYDROQUINOXALINONES AS RESPIRATORY SYNCYTIAL VIRUS ANTIVIRAL AGENTS

Quinoxalinones and dihydroquinoxalinones having inhibitory activity on RSV replication and having the formula (I) including addition salts, and stereochemically isomeric forms thereof; compositions containing these compounds as active ingredient and processes for preparing these compounds and compositions.

Structure-guided design of substituted aza-benzimidazoles as potent hypoxia inducible factor-1α prolyl hydroxylase-2 inhibitors

We report the structure-based design and synthesis of a novel series of aza-benzimidazoles as PHD2 inhibitors. These efforts resulted in compound 22, which displayed highly potent inhibition of PHD2 function in vitro.

Synthesis of 3,4-diaminopyridine and imidazo[4,5-c]pyridines by nitration of 4-acylaminopyridines

New methods for the preparation of 3,4-diaminopyridine (5) and imidazo[4,5-c]pyridines 7a,7b based on direct nitration of 4- acylaminopyridines 3a, 3b have been explored.

Hair dye compositions and process comprising and utilizing a combination of isatin and aminopyridine derivatives

The invention relates to a process for dyeing keratinous fibers, comprising the simultaneous or sequential application of a component (A) containing at least one compound of formula (I): STR1 in which: R1 denotes hydrogen, alkyl, acetyl, benzoyl, phenyl or carboxyalyl; R2 and R3 denote a hydrogen, alkyl, hydroxyl, halogen, nitro, alkylphenyl, phenyl or alkoxy; and a component (B) containing at least one compound of formula (II): STR2 in which: R4 denotes a hydrogen atom or a β-hydroxyethyl group; n=0, 1 or 2, and m=0 or 1; as well as its cosmetically acceptable salts; or one compound of formula (III): STR3 in which: R5 denotes a hydrogen atom, a hydroxyl group or a group STR4 R6 denotes a hydroxyl group or a group N STR5 R7 denotes H or NH2, R8 denotes a group STR6 R9 and R10, independently of one another, representing a hydrogen atom, a C1 -C4 alkyl, a group (CH2)p --Z, where p=1 to 4 and Z represents OH, halogen, NH2, NHR' or NHR'R", where R' and R" denote a C1 -C4 alkyl or form a heterocycle with the nitrogen atom to which they are attached; with the proviso that one of R5 to R8 denotes NH2 ; and its cosmetically acceptable salts, as well as to the dyeing agents employed.

Diaminopyridine compounds and methods of use

The present invention relates to compositions and method for inhibiting nonenzymatic cross-linking (protein aging) which contain diaminopyridines and derivates thereof. Accordingly, a composition is disclosed which comprises an agent capable of inhibiting the formation of advanced glycosylation endproducts of target proteins by reacting with the carbonyl moiety of the early glycosylation product of such target proteins formed by their initial glycosylation. The method comprises contacting the target protein with the composition. Both industrial and therapeutic applications for the invention are envisioned, as food spoilage and animal protein aging can be treated.