37751-39-6

Usage

Uses

Antidepressant.

InChI:InChI=1/C17H15ClN2O/c18-13-6-3-5-12(11-13)17(21)14-7-1-2-8-15(14)20-10-4-9-19-16(17)20/h1-3,5-8,11,21H,4,9-10H2

Upstream product

• 61272-69-3 1-(3-aminopropyl)-3-(3-chlorophenyl)-3-hydroxyindol-2(3H)-one 
• 60547-83-3 3-(m-Chlorophenyl)-2-(3-chloropropylamino)-3H-indol-3-ol hydrochloride 
• 109-64-8 1,3-dibromo-propane 
• 37603-46-6 C₁₃H₁₄N₂O₂ 
• 91-56-5 indole-2,3-dione 
• 6714-68-7 spiro[1,3-dioxolane-2,3'-indolin]-2'-one 
• 10349-82-3 3-<1'-<2'(1'H)-oxospiro<1,3-dioxolane-2,3'-indol>yl>>propanenitrile 

Downstream Products

• 136650-39-0 3-(3-chlorophenyl)-3-hydroxy-1-(3-methylaminopropyl)indol-2(3H)-one hydrochloride 
• 136650-45-8 6-(3-chlorophenyl)-1-methyl-5-(p-tolylsulphonyl)-1,2,3,4,5,6-hexahydro-1,5-benzodiazocine 
• 136650-43-6 6-(3-chlorophenyl)-1-methyl-1,2,3,4-tetrahydro-1,5-benzodiazocine 
• 136650-27-6 6-(3-chlorphenyl)-1,2,3,4,5,6-hexahydro-1,6-methano-1,5-benzodiazocin-11-one 
• 37647-89-5 10-(3-chlorophenyl)-10-hydroxy-1-methyl-2,3,4,10-tetrahydropyrimido<1,2-a>indolium iodide 
• 136650-31-2 6-(3-chlorophenyl)-5-(p-tolylsulphonyl)-1,2,3,4,5,6-hexahydro-1,6-methano-1,5-benzodiazocin-11-one 
• 136650-30-1 6-(3-chlorophenyl)-5-phenylsulphonyl-1,2,3,4,5,6-hexahydro-1,6-methano-1,5-benzodiazocin-11-one 
• 136650-34-5 10-benzoyloxy-10-(3-chlorophenyl)-2,3,4,10-tetrahydropyrimido<1,2-a>indole hydrochloride 
• 37647-85-1 10-acetoxy-10-(3-chlorophenyl)-2,3,4,10-tetrahydropyrimido<1,2-a>indole hydrochloride 

Relevant academic research and scientific papers

Oral Hypoglycemic Agents. Pyrimidoindoles and Related Compounds

A series of pyrimidoindoles were synthesized and studied for their hypoglycemic activity following oral administration at standard dose of 100 mg/kg to fed rats.The effect of 10-alkoxyalkyl, 10-alkyl, 10-aryl, and 3,3-dialkyl substitution on the activity of 10-hydroxypyrimidoindoles was investigated.Relative potencies of a number of the most active compounds were defined by three-point dose-response studies.The most potent compounds were those with either 3,3-dimethyl substituents, compounds 21, 22, and 38, or 3,3-spirocyclohexane substituents, compounds 39 and 49. 10-Aminopyrimidoindoles were in general less active than the 10-hydroxy analogues, and potency was further decreased by derivatizing the 10-amino group.The most potent 10-amino derivatives were 57 and 58.

Rearrangements of Pyrimido- and Diazepino-indoles: Syntheses of 1,5-Benzodiazocines and 1,6-Benzodiazonines

Rearrangements of the pyrimidoindoles 1 and 2 and the pyrimidoindolinium iodide 13 produce the 1,2,3,4,5,6-hexahydro-1,5-benzodiazocines 7-9.The diazepinoindole 16 produces the 2,3,4,5,6,7-hexahydro-1,6-benzodiazonine 18.Formation of compounds 7 and 8 is less facile than that of compounds 9 and 18.The pyrimidoindoles 1 and 2 and the diazepinoindole 16 undergo rearrangement with arenesulphonyl chlorides such as toluene-p-sulphonyl chloride but not with carboxylic acid chlorides to give the diazocines 10 and 12 and the diazonine 20.Mechanisms for the rearrangements are discussed in terms of indole 2,3-oxide intermediates.The reduction of the pyrimidoindole 2 with lithium tetrahydroaluminate generates the bicyclic aminal 26.The treatment of the bicyclic lactam 11 with lithium tetrahydroaluminate or with sodium methoxide results in ring-opening and formation of the 1,2,3,4-tetrahydro- and 1,2,3,4,5,6-hexahydro-1,5-benzodiazocines 27 and 28.

2-(Halo alkylamino)-3-phenyl-3H-indole-3-ols

The invention relates to indole derivatives of the formula SPC1 And their acid addition salts wherein R is hydrogen or lower alkyl, R1, R2, R3 and R4 are each hydrogen, hydroxyl, lower alkyl, lower alkoxy, trifl

Process for the preparation of diazepino[1,2-a]indoles

The invention relates to a process for preparing fused ring indole derivatives of formula (I) SPC1 wherein R1, R2, R3, R4 are each hydrogen, hydroxyl, lower alkyl, lower alkoxy, haloloweralkyl or halogen, R5 and R6 are each hydrogen or lower alkyl and m and n are 0, 1, 2 or 3 and the sum of m + n is 2 or 3, by condensing an indole derivative of formula SPC2 With a dihaloalkane of formula EQU1 The products have pharmacological activity, particularly antidepressant and hypoglycaemic activity.

Process for the preparation of 10-(halophenyl)-2,3,4,10-tetrahydropyrimido-[1,2-a]indol-10-ol

The invention concerns a process for preparing pyrimido[1,2-a]indoles of general formula (I) SPC1 wherein R is hydrogen or lower alkyl and R1, R2, R3 and R4 are each hydrogen, hydroxyl, lower alkyl, lower alkoxy, trifluoromethyl or halogen by cyclodehydrating an indole derivative of general formula (II) SPC2 The products of formula (I) are useful as antidepressants.