4424-20-8

Basic information

• Product Name: 2,3,4,5-TETRAHYDRO-1H-BENZO[D]AZEPINE
• Synonyms: BENZ-3-AZEPINE;2,3,4,5-TETRAHYDRO-1H-BENZO[D]AZEPINE;AKOS BB-9904;2,3,4,5-TETRAHYDRO-1H-BENZO[D]AZEPINE HYDROCHLORIDE;2,3,4,5-Tetrahydro-1H-3-benzazepine;1H-3-Benzazepine, 2,3,4,5-tetrahydro-;1,2,4,5-Tetrahydro-3H-benzo[d]azepine;1,2,4,5-tetrahydro-3H-3-benzoazepine
• CAS NO: 4424-20-8
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.22
• EINECS: 1312995-182-4
• Mol File: 4424-20-8.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 110-120℃ (11 Torr)
• Flash Point: 114.9±14.2℃
• Appearance: /
• Density: 0.981±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.0135mmHg at 25°C
• Refractive Index: 1.565 (589.3 nm 20℃)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.27±0.20(Predicted)
• CAS DataBase Reference: 2,3,4,5-TETRAHYDRO-1H-BENZO[D]AZEPINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5-TETRAHYDRO-1H-BENZO[D]AZEPINE(4424-20-8)
• EPA Substance Registry System: 2,3,4,5-TETRAHYDRO-1H-BENZO[D]AZEPINE(4424-20-8)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-34
• Safety Statements: 23-26-36/37/39-45
• HazardClass: IRRITANT
• Hazardous Substances Data: 4424-20-8(Hazardous Substances Data)

Usage

General Description

2,3,4,5-Tetrahydro-1H-benzo[d]azepine, also known as THBAP, is a heterocyclic chemical compound with a bicyclic structure. It is a derivative of the tricyclic antidepressant drug amoxapine and is used in the development of new pharmaceuticals. THBAP exhibits central nervous system activity and has been studied for its potential as a therapeutic agent for psychiatric and neurological disorders. It has also shown potential as an analgesic and anti-inflammatory agent. THBAP is a versatile molecule that has attracted interest in the field of medicinal chemistry for its broad range of pharmacological activities and potential therapeutic applications.

InChI:InChI=1/C10H13N/c1-2-4-10-6-8-11-7-5-9(10)3-1/h1-4,11H,5-8H2

Synthetic route

1,2-phenylenebis(ethane-2,1-diyl) dimethanesulfonate (130800-04-3) → 2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8)

Conditions	Yield
With ammonia at 90℃; for 3h; Sealed tube;	100%
Stage #1: 1,2-phenylenebis(ethane-2,1-diyl) dimethanesulfonate With ammonia In water; acetonitrile at 100℃; under 2068.65 Torr; for 1h; Stage #2: With hydrogenchloride; water In acetonitrile pH=4; Stage #3: With sodium hydroxide In diethyl ether; water; acetonitrile pH=14;	81%
With ammonia In ethanol; water at 80℃; for 0.666667h; Microwave;	73%
With ammonia In acetonitrile at 100℃; under 2068.65 Torr; for 1h; Autoclave;	20%

3-benzyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine → 2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8)

Conditions	Yield
With hydrogenchloride; palladium 10% on activated carbon In ethanol; water at 20℃; for 48h;	95%

3-formyl-2,3,4,5-tetrahydro-1H-3-benzazepine (215033-43-5) → 2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8)

Conditions	Yield
With sodium hydroxide In ethanol for 1h; Hydrolysis; Heating;	77%

1,2-phenylenediacetonitrile (613-73-0) → 2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8)

Conditions	Yield
With ammonia; hydrogen; nickel In ethanol at 50℃; under 51714.8 Torr; for 24h;	60%
With ammonia; hydrogen; Raney Nickel In methanol at 70℃; under 36201.3 Torr; for 48h;	47%
In ethanol; dichloromethane	35%

1,2-phenylenediacetonitrile (613-73-0) → 2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + 2,2'-o-phenylene-bis-ethylamine (42988-81-8)

Conditions	Yield
With ethanol; ammonia; nickel under 51485.6 Torr; Hydrogenation;

lactam of/the/ 2-<β-amino-ethyl>-phenylacetic acid → 2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8)

Conditions	Yield
With ethanol; sodium

ethanol (64-17-5) + ammonia (7664-41-7) + 1,2-phenylenediacetonitrile (613-73-0) + nickel → 2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + 2,2'-o-phenylene-bis-ethylamine (42988-81-8)

Conditions	Yield
unter Druck.Hydrogenation;

phenethylamine (64-04-0) → 2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8)

Conditions

Yield

Multi-step reaction with 6 steps 1: 63 percent / Na2CO3; NaI; tetrabutylammonium bromide / dioxane / Heating 2: 99 percent / acetic anhydride / 1 h / 60 °C 3: 92 percent / aq. NaIO4 / methanol / 1.5 h / 20 °C 4: 47 percent / TFAA; BF3*Et2O / benzene / 2 h / 20 °C 5: 77 percent / NiCl2*6H2O; NaBH4 / methanol; tetrahydrofuran / 0.33 h / 20 °C 6: 77 percent / aq. NaOH / ethanol / 1 h / Heating View Scheme

N-(2-phenylethyl)-2-phenylsulfanylethylamine (304011-19-6) → 2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 99 percent / acetic anhydride / 1 h / 60 °C 2: 92 percent / aq. NaIO4 / methanol / 1.5 h / 20 °C 3: 47 percent / TFAA; BF3*Et2O / benzene / 2 h / 20 °C 4: 77 percent / NiCl2*6H2O; NaBH4 / methanol; tetrahydrofuran / 0.33 h / 20 °C 5: 77 percent / aq. NaOH / ethanol / 1 h / Heating View Scheme

N-(2-phenylethyl)-N-(2-phenylsulfanylethyl)formamide (304011-24-3) → 2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 92 percent / aq. NaIO4 / methanol / 1.5 h / 20 °C 2: 47 percent / TFAA; BF3*Et2O / benzene / 2 h / 20 °C 3: 77 percent / NiCl2*6H2O; NaBH4 / methanol; tetrahydrofuran / 0.33 h / 20 °C 4: 77 percent / aq. NaOH / ethanol / 1 h / Heating View Scheme

3-formyl-1-phenylsulfanyl-2,3,4,5-tetrahydro-1H-3-benzazepine (304011-32-3) → 2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / NiCl2*6H2O; NaBH4 / methanol; tetrahydrofuran / 0.33 h / 20 °C 2: 77 percent / aq. NaOH / ethanol / 1 h / Heating View Scheme

N-(2-phenylethyl)-N-(2-phenylsulfinylethyl)formamide (304011-27-6) → 2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 47 percent / TFAA; BF3*Et2O / benzene / 2 h / 20 °C 2: 77 percent / NiCl2*6H2O; NaBH4 / methanol; tetrahydrofuran / 0.33 h / 20 °C 3: 77 percent / aq. NaOH / ethanol / 1 h / Heating View Scheme

1,3,4,5-tetrahydro-2H-benzo[d]azepin-2-one (15987-50-5) → 2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8)

Conditions	Yield
With borane-THF

1,2-Phenylenediacetic acid (7500-53-0) → 2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C 2: triethylamine / dichloromethane / 0.5 h / 0 °C 3: ammonia / acetonitrile / 1 h / 100 °C / 2068.65 Torr / Autoclave View Scheme
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 16 h / Reflux 2: triethylamine / dichloromethane / 0.5 h / 20 °C 3: ammonia / 3 h / 90 °C / Sealed tube View Scheme

2,2’-(1,2-phenylene)diethanol (17378-99-3) → 2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0.5 h / 0 °C 2: ammonia / acetonitrile / 1 h / 100 °C / 2068.65 Torr / Autoclave View Scheme
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0.5 h / 20 °C 2: ammonia / 3 h / 90 °C / Sealed tube View Scheme

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + trifluoroacetic anhydride (407-25-0) → 3-trifluoroacetyl-2,3,4,5-tetrahydro-1H-3-benzazepine (158726-30-8)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1h;	100%
In dichloromethane at -20 - 20℃; for 12h;	98%
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;	97%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + 4-Chlorophenyl isothiocyanate (2131-55-7) → N-(4-Chlorophenyl)-1 ,2,4,5-tetrahydro-3H-3-benzazepine-3-carbothioamide (915104-43-7)

Conditions	Yield
In dichloromethane at 20℃; for 1h;	100%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) → 1-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone (10533-22-9)

Conditions	Yield
With acetic anhydride; triethylamine In dichloromethane; water	95%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + acetic anhydride (108-24-7) → 1-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone (10533-22-9)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 18h;	95%
With triethylamine In dichloromethane	50%
With triethylamine In dichloromethane at 20℃; for 18h;

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8)

Conditions	Yield
With sulfuric acid; nitric acid; trifluoroacetic acid at 0℃; regioselective reaction;	90%
With sulfuric acid; nitric acid; trifluoroacetic acid at 0℃; for 2h;	63%
Stage #1: 2,3,4,5-tetrahydro-1H-3-benzazepine With sulfuric acid at 0℃; for 0.5h; Stage #2: With nitric acid In water at 0℃; for 2h;	25%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) → 7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine monosulfate (1241840-94-7)

Conditions	Yield
Stage #1: 2,3,4,5-tetrahydro-1H-3-benzazepine With trifluoroacetic acid for 0.5h; Inert atmosphere; Stage #2: With sulfuric acid for 0.25h; Stage #3: With nitric acid at 5 - 10℃; for 4h; regioselective reaction;	90%
With sulfuric acid; nitric acid; trifluoroacetic acid at 0 - 10℃;	86%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + ethyl N-[4-chloro-6-(2H-indazol-2-yl)pyrimidin-2-yl]-beta-alaninate → C26H28N6O2

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 1h; Microwave irradiation;	89%
In isopropyl alcohol for 2h;	83%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + N-[6-chloro-2-(2-pyridinyl)-4-pyrimidinyl]-β-alanine (1373424-45-3) → (3-((2-pyridin-2-yl)-6-(1,2,4,5-tetrahydro-3H-benzo[d]azepin-3-yl)pyrimidin-4-yl)amino)propanoic acid (1373422-53-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 150℃; for 1h; Microwave irradiation;	86%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + ethyl N-[4-chloro-6-(2H-1,2,3-triazol-2-yl)pyrimidin-2-yl]-beta-alaninate → ethyl N-[4-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-6-(2H-1,2,3-triazol-2-yl)pyrimidin-2-yl]-beta-alaninate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 1h; Microwave irradiation;	85%
In isopropyl alcohol for 2h;	35%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + ethyl N-[4-chloro-6-(1H-1,2,3-triazol-1-yl)pyrimidin-2-yl]-beta-alaninate → ethyl N-[4-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-6-(1H-1,2,3-triazol-1-yl)pyrimidin-2-yl]-beta-alaninate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 1h; Microwave irradiation;	85%
In isopropyl alcohol for 2h;	75%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + ethyl N-[4-chloro-6-(1H-pyrazol-1-yl)pyrimidin-2-yl]-beta-alaninate → ethyl N-[4-(1H-pyrazol-1-yl)-6-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)pyrimidin-2-yl]-beta-alaninate

Conditions	Yield
In isopropyl alcohol for 2h;	84%
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 1h; Microwave irradiation;	84%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + methyl 2-isocyanatobenzoate (1793-07-3) → methyl 2-(2,3,4,5-tetrahydro-1H-benzo[d]azepine-3-carboxamido)benzoate

Conditions	Yield
With triethylamine In dichloromethane at 25℃; for 2h; Inert atmosphere;	83%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + 2-(chloromethyl)-5-nitro-1H-benzo[d]imidazole (14625-39-9) → 3-((5-nitro-1H-benzo[d]imidazol-2-yl)methyl)-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Conditions	Yield
With sodium carbonate In acetonitrile at 23℃;	82%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + acetyl chloride (75-36-5) → 1-(1,2,4,5-tetrahydro-benzo[d]azepin-3-yl)-ethanone (10533-22-9)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 1h;	80%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + ethyl N-[4-chloro-6-(1,3-thiazol-2-yl)pyrimidin-2-yl]-beta-alaninate → ethyl N-[4-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-6-(1,3-thiazol-2-yl)pyrimidin-2-yl]-beta-alaninate

Conditions	Yield
In isopropyl alcohol for 2h;	80%
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 1h; Microwave irradiation;	80%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + C12H10ClN5 → C22H22N6

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In isopropyl alcohol at 160℃; for 1h; Microwave irradiation;	80%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) → C9H11N3O2

Conditions	Yield
With sulfuric acid; potassium nitrate at 5℃; for 0.166667h;	71%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + Methyl 4-(bromomethyl)benzoate (2417-72-3) → methyl 4-((1,2,4,5-tetrahydro-3H-benzo[d]azepin-3-yl)methyl)benzoate

Conditions	Yield
With potassium carbonate In acetonitrile at 85℃; for 4h;	71%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) → 7-nitro-2,3,4,5-tetrahydro-1H-benzo[d]azepine nitrate salt (118454-13-0)

Conditions	Yield
With nitric acid at -10℃; for 0.5h; Cooling with acetone-dry ice;	70%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) → C20H25N3O4S2 (82771-52-6)

Conditions	Yield
With bis(chlorosulfonyl)amine; triethylamine In dichloromethane; acetonitrile at 25℃; for 12h;	67%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + benzaldehyde (100-52-7) + β-naphthol (135-19-3) → 1-[(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)phenylmethyl]naphthalen-2-ol

Conditions	Yield
In neat (no solvent) at 60℃; for 2h; Mannich Aminomethylation; Autoclave; Microwave irradiation;	67%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + 1,1-dimethylethyl[trans-4-(2-oxoethyl)cyclohexyl]carbamate (215790-29-7) → trans-3-(2-(1-(4-(N-tert-butoxycarbonyl)amino)cyclohexyl)ethyl)-2,3,4,5-tetrahydro-1H-3-benzazepine

Conditions	Yield
Stage #1: 2,3,4,5-tetrahydro-1H-3-benzazepine; 1,1-dimethylethyl[trans-4-(2-oxoethyl)cyclohexyl]carbamate With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 0.5h; Stage #2: With water; potassium carbonate In dichloromethane; 1,2-dichloro-ethane	62%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + ethyl N-(2-{4-[2-(1,3-dioxolan-2-yl)ethyl]-2-pyridinyl}-6-{[(4-methylphenyl)sulfonyl]oxy}-4-pyrimidinyl)-β-alaninate (1373424-24-8) → ethyl N-[2-{4-[2-(1,3-dioxolan-2-yl)ethyl]-2-pyridinyl}-6-(1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl)-4-pyrimidinyl]-β-alaninate (1373424-25-9)

Conditions	Yield
In isopropyl alcohol at 150℃; for 1h; Microwave irradiation;	60%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + 4-chloro-1-(4-chlorophenyl)butan-1-one (40877-09-6) → 1-(4-chlorophenyl)-4-(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)butan-1-one hydrochloride

Conditions	Yield
Stage #1: 2,3,4,5-tetrahydro-1H-3-benzazepine; 4-chloro-1-(4-chlorophenyl)butan-1-one With potassium carbonate; potassium iodide In 1,2-dimethoxyethane at 120℃; for 1h; Sealed tube; Microwave irradiation; Stage #2: With hydrogenchloride In diethyl ether Solvent;	59%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + α-naphthol (90-15-3) + benzaldehyde (100-52-7) → 2-[(4,5-dihydro-1H-benzo[d]azepin-3(2H)-yl)-phenyl-methyl]-naphthalen-1-ol

Conditions	Yield
In neat (no solvent) at 55℃; for 1.5h; Mannich Aminomethylation; Autoclave; Microwave irradiation;	55%

2,3,4,5-tetrahydro-1H-3-benzazepine (4424-20-8) + 2-(3-{5-chloro-2-[(oxan-4-yl)amino]pyrimidin-4-yl}-5-oxo-5H,6H,7H-pyrrolo[3,4-b]pyridin-6-yl)acetic acid → 3-{5-chloro-2-[(oxan-4-yl)amino]pyrimidin-4-yl}-6-[2-oxo-2-(2,3,4,5-tetrahydro-1H-3-benzazepin-3-yl)ethyl]-5H,6H,7H-pyrrolo[3,4-b]pyridin-5-one

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In ethyl acetate; N,N-dimethyl-formamide for 1h;	51.9%

Upstream product

• 64-17-5 ethanol 
• 7664-41-7 ammonia 
• 613-73-0 1,2-phenylenediacetonitrile 
• 17378-99-3 2,2’-(1,2-phenylene)diethanol 
• 7500-53-0 1,2-Phenylenediacetic acid 
• 15987-50-5 1,3,4,5-tetrahydro-2H-benzo[d]azepin-2-one 
• 130800-04-3 1,2-phenylenebis(ethane-2,1-diyl) dimethanesulfonate 
• 695811-96-2 3-benzyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 
• 304011-27-6 N-(2-phenylethyl)-N-(2-phenylsulfinylethyl)formamide 
• 304011-32-3 3-formyl-1-phenylsulfanyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 304011-24-3 N-(2-phenylethyl)-N-(2-phenylsulfanylethyl)formamide 
• 304011-19-6 N-(2-phenylethyl)-2-phenylsulfanylethylamine 
• 64-04-0 phenethylamine 
• 215033-43-5 3-formyl-2,3,4,5-tetrahydro-1H-3-benzazepine 

Downstream Products

• 215033-43-5 3-formyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 374809-97-9 1-(3-acetyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-4-[4-(4-chlorophenyl)piperidin-1-yl]butan-1-one 
• 1345688-65-4 1-(3-acetyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-4-[4-(4-fluorophenyl)piperidin-1-yl]butan-1-one 
• 1345688-66-5 1-(3-acetyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-4-[4-(4-methylphenyl)piperidin-1-yl]butan-1-one 
• 1345688-67-6 1-(3-acetyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-4-[4-(3-methylphenyl)piperidin-1-yl]butan-1-one 
• 1345688-68-7 1-(3-acetyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-4-[4-(2-methylphenyl)piperidin-1-yl]butan-1-one 
• 1345688-43-8 4-[4-(4-chlorophenyl)piperidin-1-yl]-1-(3-propionyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)butan-1-one 
• 1345688-44-9 1-(3-butyryl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-4-[4-(4-chlorophenyl)piperidin-1-yl]butan-1-one 
• 1345688-45-0 4-[4-(4-chlorophenyl)piperidin-1-yl]-1-[3-(cyclopropylcarbonyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]butan-1-one 
• 1345688-46-1 4-[4-(4-chlorophenyl)piperidin-1-yl]-1-(3-pentanoyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)butan-1-one 
• 1345688-47-2 1-(3-benzoyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl)-4-[4-(4-chlorophenyl)piperidin-1-yl]butan-1-one 
• 1345688-48-3 4-[4-(4-chlorophenyl)piperidin-1-yl]-1-[3-(methylsulfonyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]butan-1-one 
• 1345688-49-4 4-[4-(4-chlorophenyl)piperidin-1-yl]-1-[3-(ethylsulfonyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl]butan-1-one 
• 1345688-69-8 methyl-7-{4-[4-(4-chlorophenyl)piperidin-1-yl]butanoyl}-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate hydrochloride 

Relevant articles and documents

1,2,4-Triazol-3-yl-thiopropyl-tetrahydrobenzazepines: A series of potent and selective dopamine D3 receptor antagonists

The discovery of new highly potent and selective dopamine D3 receptor antagonists has recently permitted characterization of the role of the dopamine D3 receptor in a wide range of preclinical animal models. A novel series of 1,2,4-triazol-3-yl-thiopropyl-tetrahydrobenzazepines demonstrating a high level of D3 affinity and selectivity with an excellent pharmacokinetic profile is reported here. In particular, the pyrazolyl derivative 35 showed good oral bioavailability and brain penetration associated with high potency and selectivity in vitro. In vivo characterization of 35 confirmed that this compound blocks the expression of nicotine- and cocaine-conditioned place preference in the rat, prevents nicotine-triggered reinstatement of nicotine-seeking behavior in the rat, reduces oral operant alcohol self-administration in the mouse, increases extracellular levels of acetylcholine in the rat medial prefrontal cortex, and potentiates the amplitude of the relative cerebral blood volume response to d-amphetamine in a regionally specific manner in the rat brain.

HETEROCYCLIC COMPOUNDS AS AXL INHIBITORS

Compounds of Formula I and their uses of effective AXL inhibitors and for the treatment of physical condition mediated by AXL.

USE OF ION CHANNEL MODULATORS IN THE PROPHYLAXIS AND TREATMENT OF INFLAMMATORY AND IMMUNOLOGICAL DISEASES

Use of compounds of general formula (1) and pharmacologically acceptable salts and prodrugs thereof:Formula (1) wherein A and B are CH2 or CH2CH2, R1 is hydrogen, alkyl, cycloalkyl, aryl, aralkyl or heteroaralkyl, R2, R3 and R4 are selected from hydrogen, alkyl, halogen, haloalkyl, alkoxy, alkoxycarbonyl, carboxyl, hydroxyl or cyano; X is R5CO, R5SO2, R5R7NCO, R5R7NSO2, R5SO2NR7CO or CO2R8, Y is R6CO, R6SO2, R6R7NCO, R6R7NSO2, R6SO2NR7CO or CO2R8, R5 and R6 are hydrogen, alkyl, aryl, aralkyl, heteroaryl or heteroaralkyl, R7 is hydrogen, alkyl, aryl or aralkyl, and R8 is alkyl, aryl, aralkyl, alkoxyalkyl, heteroaryl or heteroarylalkyl, provided that when X is R5CO or R5SO2, then Y is not R6CO, R6SO2 or R6R7NCO, in the manufacture of a medicament for the prophylaxis or treatment of inflammatory or immunological disease.