Specification
Field of Invention:
The present invention relates to n-arylalkyl-3-aminoalkoxyindoles, having serotonin receptor affinity useful as therapeutic agents and process for their preparation. In particular, it relates to compounds described by general formula (I), its stereoisomers, its radioisotopes, its geometric forms, its N-oxides, its polymorphs, its pharmaceutically acceptable salts, its pharmaceutically acceptable solvates, its useful bioactive metabolites and any suitable combination of the above.
Further the present invention also includes the processes for preparing such compounds of the general formula (I), its stereoisomers, its radioisotopes, its geometric forms, its N-oxides, its polymorphs, its pharmaceutically acceptable salts, its pharmaceutically acceptable solvates, its useful bioactive metabolites and also includes any suitable combination of the above.
The invention also describes various methods of administering these compounds of general formula (I), i.e. pharmaceutically acceptable dosage forms compositions and the use of such compounds and compositions in either therapy or diagnosis.
The compounds of the general formula (I) of this invention are 5-HT (Serotonin) ligands e.g. agonists or antagonists. The compounds of the general formula (I) of this invention, by the virtue of its chemical characteristic, could either independently or simultaneously modulate the melatonin receptor i.e. either these compounds are melatonergic ligands e.g. agonists or antagonists, or they interact with both 5-HT and/or as Melatonin receptors.
Thus, compounds of general formula (I) of this invention are useful for treating diseases wherein activity of either 5-HT (Serotonin) and/or Melatonin is modulated to obtain the desired therapeutic effect. Specifically, the compounds of this invention are
useful in the treatment and / or prophylaxis of conditions such as psychosis, paraphrenia, psychotic depression, mania, schizophrenia, schizophreniform disorders, anxiety, migraine headache, depression, drug addiction, convulsive disorders, personality disorders, hypertension, autism, post-traumatic stress syndrome, alcoholism, panic attacks, obsessive-compulsive disorders, chronobiological abnormalities, circadian rhythms, anxiolytic, osteoporosis, ischemic stroke, lower the risk of SIDS in young infants with low endogenous melatonin levels, reproduction, glaucoma and sleep disorders.
Hence, the compounds of general formula (I) of this invention could also be useful in treating the psychotic, affective, vegetative and psychomotor symptoms of schizophrenia and the extrapyramidal motor side effects of other antipsychotic drugs; neurodegenerative disorders like Alzheimer's disease, Parkinson's and Huntington's chorea and chemotherapy-induced vomiting; and in modulation of eating behavior and thus are useful in reducing the morbidity and mortality associated with excess weight. Background of the invention
Many diseases of the central nervous system are influenced by the adrenergic, the dopaminergic and the serotoninergic neurotransmitter systems. Serotonin has been implicated in numerous diseases and conditions, which originate from central nervous system. The list includes diseases and conditions related to sleeping, eating, perceiving pain, controlling body temperature, controlling blood pressure, depression, anxiety, schizophrenia and other bodily states. (References: Fuller, R. W., Drugs Acting on Serotoninergic Neuronal Systems, in ''Biology of Serotoninergic Transmission", ed. by Osborne N. N., J Wiley & Sons Inc. (1982), 221-247; Boullin D. J., et. aIM in "Serotonin in Mental Abnormalities", International Association for The Scientific Study of Mental Deficiency, Wiley, Checester, 1978, pp. 1-340; Barchas J. et. al., in "Serotonin and Behavior51, Academic Press, NY (1973)). Serotonin also plays an important role in the peripheral systems, such as the gastrointestinal system, where it has been found to mediate a variety of contractile, secretory and electrophysiologic effects.
Due to the broad distribution of serotonin within the body, there is a lot of interest and use, in the drugs that affect serotoninergic systems. Particularly, preferred are the compounds which have receptor-specific agonism and/or antagonism for the treatment of a wide range of disorders, including anxiety, depression, hypertension, migraine, obesity, compulsive disorders, schizophrenia, autism, certain other neurodegenerative disorders like Alzheimer, Parkinson, Huntington's chorea and chemotherapy-induced vomiting (References: Gershon M. D. et. al., 5-Hydroxytryptamine and enteric neurons. In: The Peripheral Actions of 5-
Hydroxytryptamine, edited by J. R. Fozard. New York: Oxford, 1989, p. 247-273; Saxena P. R., et. al., Journal of Cardiovascular Pharmacology (1990), supplement 15, p. 17-34).
The major classes of serotonin receptors (5-HTY7) contain fourteen to eighteen separate receptors that have been formally classified (References: Glennon et al, Neuroscience and Behavioral Reviews (1990), 14, 35; and Hoyer D. et al, Pharmacol. Rev. (1994), 46, 157-203). Recently discovered information regarding sub-type identity, distribution, structure and function suggests that it is possible to identify novel, sub-type specific agents having improved therapeutic profiles with lesser side effects. The 5-HT6 receptor was identified in 1993 (References: Monsma et al, Mol. Pharmacol. (1993), 43, 320-327; and Ruat M. et al, Biochem. Biophys. Res. Com. (1993), 193, 269-276). Several antidepressants and atypical antipsychotics bind to the 5-HT6 receptor with high affinity and this binding may be a factor in their profile of activities (References: Roth et al, J. Pharm. Exp. Therapeut. (1994), 268, 1403-1410; Sleight et al, Exp. Opin. Ther. Patents (1998), 8, 1217-1224; Bourson et al, Brit J. Pharmacol. (1998), 125, 1562-1566; Boess et al, Mol. Pharmacol., 1998, 54, 577-583; Sleight etal, Brit. J. Pharmacol. (1998), 124,556-562). In addition, 5-HT6 receptor has been linked to generalized stress and anxiety states (Reference: Yoshioka et al, Life Sciences (1998), 17/18, 1473-1477). Together these studies and observations suggest that the compound, which antagonizes 5-HT6 receptors, will be useful in treating various disorders of the central nervous system.
There is very strong evidence that Melatonin is important for the regulation of a variety of neural and endocrine functions, especially those that exhibit circadian and circannual rhythmicity. Great interest therefore lies in the possibility of making available to the clinician melatonin analogues that are metabolically more stable and have an agonist or antagonist character and of which the therapeutic effect may be expected to be superior to that of the hormone itself. PCT patent application WO 00/72815 and U.S. patent No 6,465,660B1 gives extens;ve literature on studies with Melatonin and potential therapeutic application of various ligands reported till date.
Those various effects are exerted via the intermediary of specific Melatonin receptors. Molecular biology studies have demonstrated the existence of a number of receptor sub-types that are capable of binding that hormone (Trends Pharmacol. Sci., 1995, 16, p. 50; WO 97 04094). Melatonin acts on the CNS to affect neural mechanisms through receptors located in the brain. Additionally, a number of studies indicate the existence of direct effects of Melatonin in peripheral organs via peripheral melatonin receptors. Melatonin receptors are present in the heart, lungs, prostate gland, gonads, white blood cells, retina, pituitary, thyroid, kidney, gut and blood
vessels (Withyachumnarnkul ei alM Life Sci, 12 65, 1986). Three Melatonin receptor subtypes have been identified so far MT-I , MT-2 and Mel 1 c (Barreft et al., Biol. Signals Recept, 1999, 8: 6-14).
There is evidence suggesting both Melatonin agonists and antagonists would be of potential therapeutic use for a variety of maladies and conditions. PCT application WO 00/72815 and U.S patent No. 6;465,660B1 discuss in depth applications and use of such compounds and details of which are incorporated herein by reference. Also U.S. patent 6,465,660 and U.S. patent application publication number U.S. 2003/0105087 discuss some tricyclic indole and tricyclic azaindole derivatives having very valuable pharmacological characteristics in respect of melatoninergic receptors.
U.S. Patent. No. 4,839,377 and U.S. Patent. No. 4,855,314 refers to 5-substituted 3-aminoalkyl indoles. The compounds are said to be useful for the treatment of migraine.
British Patent 2,035,310 refers to 3-aminoaikyl-1H-indole-5-thioamides and carboxamides. The compounds are said to be useful in treating hypertension, Raymond's disease and migraine.
European Patent Publication 303,506 refers to 3-polyhydropyridyl-5-substituted-1H-indoles. The compounds are said to have 5-HTi receptor agonists and vasoconstrictor activity and to be useful in treating migraine. European Patent Publication 354,777 refers to N-piperidinylindolyiethyl-alkane sulfonamide derivatives. The compounds are said to be 5-HTi receptor agonists and have vasoconstrictor activity and are useful in treating cephalic pain.
European Patent Publication 438,230, refers to indole-substituted five-membered heteroaromatic compounds. The compounds are said to have "5-HTHike" receptor agonist activity and to be useful in the treatment of migraine and other -disorders for which a selective agonist of these receptors is indicated.
European Patent Publication 313,397 refers to 5-heterocyclic indole derivatives. The compounds are said to have exceptional properties for the treatment and prophylaxis of migraine, cluster headache and headache associated with vascular disorders. These compounds are also said to have exceptional "5-HTrlike" receptor agonism.
International Patent Publication WO 91/18897 refers to 5-heterocyclic indole derivatives. The compounds are said to have exceptional properties for the treatment and prophylaxis of migraine, cluster headache, and headache associated with vascular disorders. These compounds are also said to have exceptional "5-HTrlike" receptor agonism.
European Patent Publication 457,701 refers to aryloxy amine derivatives as having high affinity for 5-HT1D serotonin receptors. These compounds are said to be useful for treating diseases related to serotonin receptor dysfunction, for example, migraine.
European Patent Publication 497,512 A2, refers to a class of imidazole, triazole and tetrazole derivatives that are selective agonists for "5-HTrlike" receptors. These compounds are said to be useful for treating migraine and associated disorders.
International Patent Publication WO 93/00086 describes a series of tetrahydrocarbazole derivatives, as 5-HTj receptor agonists, useful for the treatment of migraine and related conditions.
International Patent Publication WO 93/23396, refers to fused imidazole and triazole derivatives as 5-HTi receptor agonists, for the treatment of migraine and other disorders.
Schoeffter P. et al. refers to methyl 4-{4-[4-(1,1,3-trioxo-2H-1,2-benzoisothiazol-2-yl)butyl]-1-piperazinyl}1H-indole-3-cartoxylate as a selective antagonist for the 5~HT1A receptor in their paper "SDZ216-525, a selective and potent 5-HT1A receptor antagonist", European Journal of Pharmacology, 244, 251-257 (1993).
International Patent Publication WO 94/06769, refers to 2-substituted-4-piperazine-benzothiophene derivatives that are serotonin 5-HT1A and 5-HTiD receptor agents useful in the treatment of anxiety, depression, migraine, stroke, angina and hypertension. Summary of the Invention:
The present invention relates to compounds of general formula (I), its stereoisomers, its radioisotopes, its geometric forms, its N-oxide, its polymorphs, its pharmaceutically acceptable salts, its pharmaceutically acceptable solvates, its useful bio-active metabolites and any suitable combination of the above.
The compounds of general formula (I) are as follows,
wherein R1f R2) R3, R4, Rs, Re, R7, Rs, R9, R10, Rn and R12 may be same or different, and represent hydrogen, halogen, perhaloalkyl, hydroxy, thio, amino, nitro, cyano, formyl, amidino, guanidino, substituted or unsubstituted groups selected from linear or branched (CrC12)aiky!) (C2-C12)alkenyl, /-indol-3-ol 340/342
Description 50: 1-(3-Hydroxyindoi-1-yl)ethanone (D 50)
According to the methods given in literature following N-acetylindoxyls were prepared and listed as below. These compounds were identified by IR, NMR and mass spectral analyses.
List - 3:
Description Mass ion
(M+H)+
D50 1-(3-Hydroxyindol-1-yl)ethanone 176
D51 1-(5-Bromo-3-hydroxyindol-1-yI)ethanone 254 / 256
D52 1-(5-Chloro-3-hydroxyindol-1-yl)ethanone 210 / 212
D53 1-(5-Fluoro-3-hydroxyindoM-yl)ethanone 194
D54 1-(6-Chloro-3-hydroxyindoM-yl)ethanone 210 / 212
D55 1-(3-Hydroxy-5-methoxyindol-1-yl)ethanone 206
D56 1-(5,7-Dibromo-3-hydroxyindol-1-yl)ethanone 332 / 334 /
336
D57 1-(6-Chloro-5-methoxy-3-hydroxyindol-1-yl)ethanone 240 / 242
D58 1-(6-Chloro-5-fluoro-3-hydroxyindol-1-yl)ethanone 228 / 230
D59 1-(6-Bromo-5-methoxy-3-hydroxyindol-1-yl)ethanone 284 / 286
D60 1-(6-Bromo-5-fluoro-3-hydroxyindol-1-yl)ethanone 272 / 274
D61 1-(4-Chloro-5-fluoro-3-hydroxyindol-1-yl)ethanone 228/230
D62 1-(4-Methoxy-5-fluoro-3-hydroxyindol-1-yl)ethanone 224
D63 1-(3-Hydroxy-2-phenyindol-1-yl)ethanone 252
D64 1-(5-Bromo-3-hydroxy-2-phenylindol-1-yl)ethanone 330 / 332
D65 1-(5-Chloro-3-hydroxy-2-phenylindol-1-yl)ethanone 286/288
D66 1-(5-Fluoro-3-hydroxy-2-phenylindol-1-yi)ethanone 270
D67 1-(6-Chloro-3-hydroxy-2-phenylindol-1-yl)ethanone 286 / 288
D68 1-(3-Hydroxy-5-methoxy-2-phenylindol-1-yl)ethanone 282
D69 1-(5,7-Dibromo-3-hydroxy-2-phenylindol-1-yl)ethanone 408 / 410 /
412
D70 1-(6-Chloro-5-methoxy-3-hydroxy-2-phenylindol-1-yl)ethanone 316/318
D71 1-(6-Chloro«5-fluoro-3-hydroxy-2-phenylindol-1-yl)ethanone 304
D72 1-(6-Bromo-5-methoxy-3-hydroxy-2-phenylindol-1-yl)ethanone 360/362
D73 1-(6«Bromo-5-fluoro-3-hydroxy-2-phenylindol-1-yl)ethanone 348 / 350
D74 1-(4-Chloro-5-fluoro-3-hydroxy-2-phenylindol-1-yl)ethanone 304 / 306
D75 1-(4-Methoxy-5-fluoro-3-hydroxy-2-phenyIindol-1-yl)ethanone 300
D76 1-(3-Hydroxy-2-methyIindoM-yI)ethanone 190
D77 1-(5-nromo-3-hyrtrnxy-2-methylindol-1-yl)ellia[ioriu 268 / 270
D78 1-(5-Chloro-3-hydroxy-2-methylindoI-1-yl)ethanone 224
D79 1-(5-Fluoro-3-hydroxy-2-methylindol-1-yi)ethanone 208
D80 1-(6»ChlorO"3-hydroxy-2-methylindol«1-yI)ethanone 224 / 226
D81 1-(3-Hydroxy-5-methoxy-2-methyIindoM-yl)ethanone 220
D82 1-(57-Dibromo«3-hydroxy-2-methylindol-1-yl)ethanone 346 / 348 /
350
D83 1-(6«Chloro-5-methoxy-3-hydroxy«2-methylindol-1-yl)ethanone 254 / 256
D84 1-(6«ChIoro«5-fluoro-3-hydroxy-2-methylindol-1-yl)ethanone 242/244
D85 1-(6«Bromo«5-methoxy-3-hydroxy"2-methylindol-1-yl)ethanone 298 / 300
D86 1-(6-Bromo-5-fluoro-3-hydroxy-2-methylindol"1-yl)ethanone 286 / 288
D87 1-(4«Chloro-5-fluoro-3-hydroxy-2-methylindol«1-yl)ethanone 242 / 244
D88 1-(4«Methoxy-5-fluoro-3-hydroxy-2-methylindol-1-yl)ethanone 238
Description 89: [2-{1-Acetyl-1H-indol-3-yloxy)ethyl]dimethylamine (D 89)
According to the methods given in literature (US patent 3 860 608) following derivatives were prepared and listed as below. These compounds were identified by IR, NMR and mass spectral analyses. The following procedure also describes the method of synthesis of the same.
1-Acetyl-3-indoxyl (0.015 mole), was taken in three necked flask along with potassium carbonate (0.030 mole); tetrahydrofuran (ca 15 ml_) and N,N-dimethyiaminoethyl chloride (ca 15 % solution in toluene; 0.015 mole) and the mixture was refluxed for 3 hours. Another lot of N,N-dimethylaminoethyl chloride (ca 15 % solution in toluene; 0.015 mole) was added and the reaction mixture was refluxed for further 3 hours. The reaction mixture was cooled to 25 °C and filtered. The filtrate was washed with water and brine; dried over sodium sulfate; organic solvens were removed under reduced pressure and the residue was purified by column chromatography, on silica gel; using hexane (100 %) to triethylamine : ethyl acetate (2 : 98) gradual gradient as mobile phase, to obtain the compound of general formula (I) as thick oil, which was identified by IR, NMR and mass spectral analyses. The final desired compound of general formula (X) can be further purified by preparation of their
acid addition salts.
List - 4:
Description Mass ion
(M+H)+
D89 [2-(1-Acetyl-1W-lndol-3-yloxy)ethyl]dimethylamine 247
D90 [2-(1-Acetyl-2-Phenyl-1H-indol-3-yloxy)ethyl]dimethylamine 323
D91 [2-(1-Acetyl-2-Methyl-1W-indol-3-yloxy)ethyl]dimethyiamine 261
D92 [2-(1-Acetyl-5-Bromo-1/y-indol-3-yloxy)ethyl]dimethylamine 325/327
D93 [2-(1-Acetyl-5-Bromo-2-phenyl-1«-indol-3-yloxy)ethyl]dimethylamine 401/403
D94 [2-(1-Acetyl-5-Bromo-2-methyl-1W-indol-3-yloxy)ethyl]dimethylamine 339/341
D95 [2-(1-Acetyl-5-Chloro-1/y-indol-3-yloxy)ethyl]dimethylamine 281/283
D96 [2-(1-Acetyl-5-Chloro-2-phenyl-1 Ay-indol-3-yloxy)ethyl]dimethylamine 357/359
D97 [2-(1-Acetyl-5-Chloro-2- methyl -1W-indol-3-yloxy)ethyl]dimethylamine 295/297
D98 [2-(1-Acetyl-6-Chloro-1H-indol-3-yioxy)ethyl]dimethylamine 281/283
D99 [2-(1-Acetyl-6-Chloro-2-phenyl-1H-indol-3-yloxy)ethyl]dimethylamine 357/359
D100 [2-(1-Acetyl-6-Chloro-2-methyl-1H-indol-3-yloxy)ethyl]dimethylamine 295/297
D101 [2-(1-Acetyl-5,7-Dichloro-1/V-indol-3-yloxy)ethyl]dimethylamine 315/31II
319
D102 [2-(1-Acetyl-5,7-Dichloro-2-phenyl-1H-indol-3-yloxy)ethyl]dimethylamine 391/393/
395
D103 [2-(1-Acetyi-5,7-Dichloro-2-methyl-1H-indol-3-yloxy)ethyl]dimethylamine 329/331/
333
D104 [2-(1-Acetyl-5,7-Dibromo-1H-indol-3-yloxy)ethyl]dimethylamine 403/405/
407 D105 [2-(1-Acetyl-5,7-Dibromo-2-phenyl-1H-indol-3-yloxy)ethyl]dimethylamine 479/481/
483 D106 [2-(1-Acetyl-5,7-Dibromo-2-methyl-1H-indol-3-yloxy)ethyl]dimethylamine 417/419/
421
D107 [2-(1-Acetyl-7-Bromo-5-chloro-1tf-indol-3-yloxy)ethyl]dimethylamine 359/361
D108 [2-(1-Acetyl-7-Bromo-5-chloro-2-phenyl-1rV-indol-3- 435/437
yloxy)ethyl]dimethylamine
D109 [2-(1-Acetyl-7-Bromo-5-chloro-2-methyl-1tf-indol-3- 373/375
yloxy)ethyl]dimethylamine
D110 [2-(1-Acetyl-5-Methoxy-1H-indol-3-yloxy)ethyl]dimethylamine 277
D111 [2-(1-Acetyl-5-Methoxy-2-phenyl-1H-indol-3-yloxy)ethyl]dimethylamine 353 D112 [2-(1-Acetyl-5-Methoxy-2-methyl-1H-indol-3-yloxy)ethyl]dimethylamine 291
Description 113: [2-(1H-indol-3-yloxy)ethyl]dimethylamine (D 113)
According to the methods given in literature (US patent 3 860 608) the above derivatives were deacetylated. These compounds were identified by IR, NMR and
mass spectral analyses. The following procedure also describes the method of synthesis of above compounds,
[2-(1-Acetyl-1/-/-indol-3-yloxy)ethyl]dimethylamine (0.015 mole), was taken in three necked flask along with sodium hydroxide (0.022 mole), water (ca 15 ml_) and methanol (ca 15 ml_). The reaction mixture was refluxed for 30 minutes to 2 hours. The reaction mixture was cooled to 25 °C and poured on to ice-cold water. The compound was extracted with ethyl acetate (3 X 20 mL), the combined organic extracts were washed with water and brine; dried over sodium sulfate; organic solvents were removed under reduced pressure and the residue was purified by column chromatography, on silica gel; using hexane (100 %) to triethylamine : ethyl acetate (2 : 98) gradual gradient as mobile phase, to obtain the compound of general formula (I) as thick oil, which was identified by IR, NMR and mass spectral analyses. The final desired compound of general formula (IV) can be further purified by preparation of their acid addition salts.
List - 5:
Description
D113 [2-(1A/-lndol-3-yloxy)ethyl]dimethylamine
D114 [2-(2-Phenyl-1 tt-indol-3-yloxy)ethyl]dimethylamine
D115 [2-(2-Methyl-1/Y-indol-3-yloxy)ethyl]dimethylamine
D116 [2-(5-Bromo-1/Y-indol-3-yloxy)ethyl]dimethylamine
D117 [2-(5-Bromo-2-phenyi-1 W-indol-3-yloxy)ethyl]dimethylamine
D118 [2-(5-Bromo-2-methyl-1tt-indol-3-yloxy)ethyl]dimethylamine
D119 [2-(5-Chloro-1H-indol-3-yloxy)ethyl]dimethylamine
D120 [2-(5-Chloro-2-phenyl-1 W-indol-3-yloxy)ethyl]dimethylamine
D121 [2-(5-Chloro- 2- methyl -1W-indol-3-yloxy)ethyl]dimethylamine
D122 [2-(6-Chloro-1 W-indol-3-yloxy)ethyl]dimethylamine
D123 [2-(6-Chloro-2-phenyl-1tf-indol-3-yloxy)ethyl]dimethylamine
D124 [2-(6-Chloro-2-methyl-1 H-indol-3-yloxy)ethyl]dimethylamine
D125 [2-(5,7-Dichloro-1H-indol-3-yloxy)ethyl]dimethylamine
D126 [2-(5,7-Dichloro-2-phenyl-1 H-indol-3-yloxy)ethyl]dimethylamine
D127 [2-(5,7-Dichloro-2-methyl-1/y-indol-3-yloxy)ethyl]dimethylamine
D128 [2-(5,7-Dibromo-1 AY-indol-3-yloxy)ethyl]dimethylamine
D129 [2-(5,7-Dibromo-2-phenyl-1 H-indol-3-yloxy)ethyl]dimethylamine
Mass ion (M+H)+
205
281
219
283/285
359/361
297/298
239/241
315/317
253/255
239/241
315/317
253/255
273/275/
277
349/351/
353
287/289/
291
361/363/
365
437/439/
441
D130 [2-(5,7-Dibromo-2-methyl-1H-indol-3-yloxy)ethyl]dimethylamine 375/377/
379
D131 [2-(7-Bromo-5-chloro-1H-indol-3-yloxy)ethyl]dimethylamine 317/319/
321
D132 [2-(7-Bromo-5-chloro-2-phenyl-1 H-indol-3-yloxy)ethyl]dimethylamine 393/395/
397
D133 [2-(7-Bromo-5-chloro-2-methyl-1W-indol-3-yloxy)ethyl]dimethylamine 331/333/
335
D134 [2-(5-Methoxy-1H-indol-3-yloxy)ethyl]dimethylamine 235
D135 [2-(5-Methoxy-2-phenyl-1 H-indol-3-yloxy)ethyl]dimethylamine 311
D136 [2-(5-Methoxy-2-methyl-1H-indol-3-yloxy)ethyl]dimethylamine 249
Example-1 : [2-(1-(4'-Bromobenzenesulfonyl)-1H-indol-3-yloxy)ethyl]
dimethylamine
Sodium hydride (60 % in mineral oil, 16.5 mmoles) was stirred with dimethyl formamide (ca 8 mL) in a ice-cooled, three necked round bottom flask. A solution of [2-(1H-indol-3-yloxy)ethyl]dimethylamine (15 mmole), in dimethyl formamide (ca 5 mL) was then added dropwise to this cooled suspention of sodium hydride. After the addtion was complete, the reaction mixture was allowed to attain the room temperature (25 °C). After about one hour of stirring at 25 °C, a solution of 4-Bromobenzenesulfonyl chloride (18 mmole) was added dropwise to this solution. The reaction was further stirred at 25 °C for next 3-4 hours. After the completion of reaction (TLC), reaction mixture was poured on the ice cooled water and extracted by Ethyl acetate (3 X 20 mL). The combined organic extract was washed with water and brine, dried over sodium sulphate and the volatiles were evaporated under vacuume to get the product as a thick dark oil. The residue was purified by column chromatography, on silica gel; using hexane (100 %) to triethylamine : ethyl acetate (2 : 98) gradual gradient as mobile phase, to obtain the compound of general formula (I) as thick oil, which was identified by IR, NMR and mass spectral analyses. The final desired compound of general formula (I) can be further purified by preparation of their acid addition salts. Melting range (°C) : Isolated as oil ; Mass (m/z) ; 423, 425 (M+H)+.;IR spectra (cm*1) :1150 (S02); 1H-NMR (ppm): 2.40 (s, 6H); 2.33-2.88 (t, 2H, J = 5.4 Hz); 4.11-4.16 (t, 2H, J = 5.4 Hz); 6.87 (s, 1H); 7.19-7.38 (m, 3H); 7.50 - 7.67 (m, 4H); 7.95-7.99 (d, 1H).
Example - 2 : [2-(1-(2'-Bromo-4)-methylbenzenesulfonyl)-1H-indol-3-yloxy)
ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as
oil; IR spectra (cm"1) :1150 (S02), 2900 (C-H stretch) ; Mass (m/z) :437, 439 (M+H)+; 1H-NMR (ppm) : 2.33 (s, 3H);2.38 (s,6H); 2.80-2.85 (t, 2H, J = 5.4 Hz); 4.12-4.17(t, 2H, j = 5.4 Hz); 7.13 (s, 1H); 7.20 - 7.26 (m, 3H); 7.47 (d, 1H); 7.57-7.58 (m, 1H);7.77-7.81(m,2H)
Example - 3 : [2-(1-{2'-BromobenzenesuIfonyI)-1H-indol-3-yIoxy)ethyl]
dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1) :1150 (S02), 2900 (C-H stretch) ; Mass (m/z) : 423, 425 (M+H)+; 1H-NMR (ppm) : 2.36(s, 6H); 2.77-2.83 (t, 2H, J = 5.4 Hz); 4.11-4.16 (t, 2H, J = 5.4 Hz); 7.13(s, 1H); 7.18-7.41(01, 4H); 7.59-7.84(m, 4H)
Example - 4 : ^-(l^-FluorobenzenesulfonyO-IH-indol-S-yloxyJethyl]
dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1) :1150 (S02), 2900 (C-H stretch) ; Mass (m/z) : 363 (M+H)+; 1H-NMR (ppm) : 2.38 (s, 6H); 2.80-2.86 (t, 2H, J = 5.4 Hz); 4.09-4.15 (t, 2H, J = 5.4 Hz); 6.88 (s,1H); 7.01-7.10 (m,2H); 7.22-738 (m, 2H); 7.51-7.55 (dd,1H); 7.78-7.85 (m,2H); 7.96-8.00(dd,1H)
Example - 5 : [2-(1-(4,-Chlorobenzenesulfonyl)-1H-indol-3-yloxy)ethyl]
dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil ; IR spectra (cm'1) :1150 (S02), 2900 (C-H stretch) ; Mass (m/z) : 379.1 (M+H)+; 1H-NMR (ppm) : 2.36 (s, 6H); 2.79-2.82 (t, 2H, J = 5.4 Hz); 4.07-4.13 (t, 2H, J = 5.4 Hz); 6.87 (s,1H); 7.18-7.38 (m,4H); 7.52-7.56 (dd,1H); 7.51-7.55 (dd;1H); 7.69-7.76 (d,2H); 7.95-7.99 (d,1H)
Example - 6 : ^-(l-l^-MethylbenzenesulfonyO-IH-indol-S-yloxyJethyl]
dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm'1) :1150 (S02), 2900(C-H stretch); Mass (m/z) :359.3 (M+H)+
Example - 7 : [2-(1-(4MsopropylbenzenesuIfonyl)-1H-indol-3-yloxy)ethyl]
dimethylamine
Using essentially the general procedure described in example 1 and some non-critical
variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR
spectra (cm-1): 1155; Mass (m/z) : 387 (M+H)+;
Example - 8 : [2-(1-(2,-Bromo-4,-methoxybenzenesulfonyl)-1H-indol-3-
yloxy)ethy!]dimethyla;nine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR .spectra (cm"1): 1150; Mass (m/z): 453, 455 (M+H)+;
Example - 9 : [2-(1-(BenzenesuIfonyl)-1H-indol-3-yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1): 1152; Mass (m/z): 345 (M+H)+;
Example - 10 ; ^-(I^S'^'-DimethoxybenzenesulfonylJ-IH-indol-S-yloxyJethyl]
dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1) ; 1150; Mass (m/z): 405 (M+H)+;
Example - 11 : [2-(1-Benzenesulfonyl)-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1) : 1150; Mass (m/z) : 421.5 (M+H)+;
Example- 12 : [2-(1-(4'-Fluorobenzenesulfonyl)-2-phenyl-1H-indol-3-yloxy)
ethyljdimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm'1): 1150; Mass (m/z): 439.4 (M+H)+;
Example - 13 : [2-(1-(4'-BromobenzenesuIfonyl)-2-phenyI-1H-indol-3-
yloxy)ethyi]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1): 1150; Mass (m/z): 499, 501 (M+H)+;
Example - 14 : ^-(l^-lsopropylbenzenesulfonyO^-phenyMH-indol-S-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil ; IR spectra (cm"1): 1155; Mass (m/z): 463.4 (M+H)+;
Example -15 : ^(l-tS'^'-DimethoxybenzenesulfonyO^-phenyl-IH-indol-S-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1): 1153; Mass (m/z): 481.3 (M+H)+;
Example -16 : [2-(1-(4'-MethylbenzenesulfonyI)-2-phenyl-1H-indol-3-
y!oxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm~1): 1154; Mass (m/z) : 435.3 (M+H)+;
Example -17 : ^-(l^'-Chlorobenzenesulfonyl^-phenyl-IH-indol-S-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) : 1150; Mass (m/z): 455, 457 (M+H)+;
Example - 18 : ^-(l^'-Bromo-^-MethylbenzenesulfonyO^-phenyl-IH-indol-S-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1); 1152; Mass (m/z): 513, 515 (M+H)+;
Example -19 : [2-(1-(2,-Bromo-4,-Methoxybenzenesulfonyl)-2-phenyl-1H-indol-
3-yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1): 1150; Mass (m/z): 529, 531 (M+H)+;
Example - 20 : [2-(1 -^'-BromobenzenesulfonylJ^-phenyM H-indol-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1): 1154; Mass (m/z): 499, 501 (M+H)\*
Example - 21 : [2-(1-Benzenesulfonyf)-2-methyl-1H-indol-3-yloxy)ethyl]
dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C); Isolated as oil; IR spectra (cm-1): 1155; Mass (m/z): 359.3 (M+H)+;
Example - 22 : ^-(l^'-fluorobenzenesulfonyO^methyl-IH-mdol-S-yloxy)
ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1): 1150; Mass (m/z): 377.3 (M+Hf;
Example - 23 : [2-(1-(4'-Bromobenzenesulfonyl)-2-methyl-1H-indol-3-yloxy)
ethyljdimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1) : 1150; Mass (m/z): 437, 439 (M+H)+;
Example - 74 : [2-(1-(4;-lsopropylbenzenesulfonyl)-2-methyl-1H-indol-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1): 1152; Mass (m/z): 401.4 (M+H)+;
Example - 25 : ^-(l-tS'^'-DimethoxybenzenesulfonyO^-methyMH-indol-a-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical
variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR
spectra (cm"1): 1154; Mass (m/z): 419.5 (M+H)+;
Example - 26 : ^-(l^'-BromobenzenesuIfonyO^-methyMH-indol-S-
yloxy)ethyI]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical
variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR
spectra (cm"1): 1155; Mass (m/z): 437, 439 (M+H)+;
Example - 27 : ^(l^-Bromo-^-MethylbenzenesuIfonyO^-methyl-IH-indol-S-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical
variations, the above derivative was prepared. Melting range (°C) ; Isolated as oil; IR
spectra (cm'1): 1150; Mass (m/z): 451, 453 (M+H)+;
Example - 28 : ^-(l^'-Bromo-^-methoxybenzenesulfonyO^-methyl-IH-indol-
3-yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1): 1150; Mass (m/z): 467, 469 (M+H)+;
Example - 29 : [2-(1-(4'-ChlorobenzenesuIfonyi)-2-methyl-1H-indol-3-yloxy)
ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil ; IR spectra (cm"1): 1154; Mass (m/z): 394, 396 (M+Hf;
Example - 30 : [2-(1-(4'-lsoprpyibenzenesulfonyl)-5-bromo-1H-indol-3-yloxy)
ethyljdimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : 105 - 107; IR spectra (cm-1) : 1174.57(S02), 2962, 2967(C-H Streching); Mass(m/z) : 465, 467.3 (M+H)+; 1H-NMR (ppm) :1.17 - 1.2 (d, 6H,); 2.2 (s, 6H); 2.78 (t, 2H, J = 5.4 Hz); 2.81
(septet, 1H); 4.06 - 4.11 (t, 2H, J = 5.4 Hz); 6.918 (s, 1H); 7.22 - 7.26 (d, 2H); 7.39 -7.44 (dd, 1H); 7.67 - 7.9 (m, 4H);
Example - 31 : [2-(1-(2,«Bromobenzenesulfonyl)-5-bromo-1H«indol-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) ; Isolated as oil ; IR spectra (cm-1) :1178.49 (S02) ; Mass (m/z) : 501, 503, 505 (M+H)+; 1H-NMR (ppm) : 2.3 (s, 6H); 2.74 (t, 2H); 4.02 - 4.08 (t, 2H); 7.04 (s, 1H); 7.29 - 7.35 (m, 3H); 7.52 -7.81 (mf 4H)
Example - 32 : [2-(1-Benzenesulfonyl)-5-bromo-1H-fndol-3-yloxy)ethyl]
dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; 224 - 226 (HCI salt); IR spectra (cnrf1) :1176.32 (S02); Mass (m/z) :423, 425 (M+H)+ ; 1H-NMR (ppm) : D3.02 (s, 6H); 3.65-3.67 (t, 2H, J = 5.4 Hz); 4.43-4.47 (t, 2H, J = 5.4 Hz); 7.37 (s, 1H); 7.48-7.64, (m, 4H); 7.78-7.79 (d, 1H); 7.94-7.99 (m,3H)
Example - 33 : [2-(1-(4'-Fluorobenzenesulfonyl)-5-bromo-1H-indol-3-yloxy)
ethyljdimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : 74 - 75; IR spectra (cm"1) :1180.57(SO2) ; Mass (m/z) : 441, 443 (M+H)~: 1H-NMR (ppm) : D2.35 (s,6H); 2.73-2.79 (t, 2H, J = 5.4 Hz); 4.04-4.1 (t, 2H, J = 5.4 Hz); 6.87 (s, 1H); 7.08-7.12 (d, 2H); 7.40-7.45 (dd, 1H); 7.68-7.83 (m,4H).
Example - 34 : ^-(l^'-Bromo^-methoxybenzenesulfonylJ-S-bromo-IH-indol-S-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1): 1150; Mass (m/z): 531, 533, 535 (M+Hf;
Example - 35 : [2-(1-(2'-Bromo-4,-methylbenzenesulfonyl)-5-bromo-1H-indol-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical
variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1): 1154; Mass (m/z): 515, 517 (M+H)+;
Example - 36 ; [2-(1 -^^-DimethoxybenzenesulfonylJ-S-bromo-l H-indol-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1): 1154; Mass (m/z): 483, 485 (M+H)+;
Example - 37 : [2-(1-(4'-Bromobenzenesulfonyl)-5-bromo-1H-indol-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1): 1154; Mass (m/z): 501, 503, 505 (M+H)+;
Example - 38 : [2-(1-(4'-ChlorobenzenesulfonyI)-5-bromo-1H-indol-3-yloxy)
ethyljdimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1): 1155; Mass (m/z): 457, 459, 461 (M+H)+;
Example - 39 ; p^l^'-MethylbenzenesulfonylJ-S-bromo-IH-indol-S-yloxy)
ethyljdimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1) :1166 (S02) ; Mass (m/z) : 437, 439 (M+H)+; 1H-NMR (ppm) : D2.35 (s, 3H); 3.01 (s, 6H); 3.65-3.70 (t, 2H, J = 5.4 Hz); 4.42-4.47 (t, 2H, J = 5.4 Hz); 7.33-7.34 (d,2H); 7.47-7.81 (d, 5H); 7.91-7,96 (d,1H). Example - 40 : [2-(1 -(2,-Bromo-4,-methylbenzenesulfonyl)-5-bromo-2-MethyI-1 H-
indol-3-yloxy)ethyl]dimethylamine Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm'1) :1166 (S02); Mass (m/z): 329, 531, 533 (M+H)+;
Example - 41 : [2-(1-(2'-BromobenzenesulfonyI)-5-bromo-2-methyl-1H-indoI-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1) :1166 (S02); Mass (m/z): 515, 517, 519 (M+H)+;
Example - 42 : [2-(1-(4'-FluorobenzenesuIfonyl)-5-bromo-2-methyI-1 H-indol-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1) :1166 (S02); Mass (m/z): 455, 457 (M+H)+ ;
Example - 43 : [2-(1-(4'-FluorobenzenesuIfonyl)-5-bromo-2-phenyl-1 H-indol-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cnT1) :1166 (S02); Mass (m/z): 517, 519 (M+H)+;
Example - 44 : [2-(1-(4,-ChIorobenzenesulfony!)-5-bromo-2-phenyl-1H-indol-3-
yIoxy)ethyI]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm'1) :1166 (S02); Mass (m/z): 533, 535, 537 (M+H)+;
Example - 45 : ^-(l^'-FluorobenzenesulfonyO-SJ-dibromo-IH-indol-S-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm'1) ;1160 (S02); Mass (m/z): 519, 521, 523 (M+H)+;
Example - 46 : [2-(1-(4'-ChlorobenzenesulfonyI)-5,7-dibromo-1H-indol-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) ; Isolated as oil; IR spectra (cm-1) :1166 (S02); Mass (m/z); 535, 537, 539 (M+H)+;
Example - 47 : ^-(l^'-FluorobenzenesulfonyO-SJ-dibromo^-phenyl-IH-indol-
3-yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) :1166 (S02); Mass (m/z): 595, 597, 599 (M+H)+;
Example - 48 : p-CI^-MethylbenzenesulfonyO-S^-dJbromo^-methyl-IH-indoI-
3-yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) :1166 (S02); Mass (m/z): 529, 531, 533 (M+H)+;
Example - 49 : ^-(l^'-FluorobenzenesulfonyO-e-chloro-IH-indoI-S-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C): Isolated as oil ; IR spectra (cm"1): 1165; Mass (m/z): 397, 399 (M+H)+; 1H-NMR (SDDppm): 2.37 (s,6H); 2.77-2.83 (t, 2H, J = 5.4 Hz); 4.06-4.12 (t, 2H, J = 5.4 Hz); 6.86 (s,1H); 7.06-7.26 (m, 3H); 7.44-7.48 (d, 1H); 7.79-7.86 (m, 2H); 8.00-8.01 (d,1H).
Example - 50 : [2-(1-(2,-Bromobenzenesulfonyl)-6-chloro-1H-indoi«3-yloxy)
ethyljdimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm'1) : 1160; Mass (m/z) : 457, 459, 461 (M+H)+;
Example - 51 : ^-(l^'-MethylbenzenesulfonyO-e-chloro-IH-indoI-S-yloxy)
ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) :1173.4 (S02); 812,786 (C-CI) Mass (m/z) : 393, 395 (M+H)+ ; 1H-NMR(5DDppm): 2.35 (s, 9H, CH3and NMe2); 2.74-2.8 (t, 2H, J = 5.4 Hz); 4.05-4.10 (t, 2H, J = 5.4 Hz); 6.88 (s,1H); 7.15-7.26 (m, 3H); 7.42-7.46 (d,1H); 7.66-7.71 (d,2H); 8.01-8.02 (d,1H).
Example - 52 : [2-(1-BenzenesuIfonyl)-6-chloro-1H-indol-3-yloxy)ethyl]
dimethylamine
Using essentially the general procedure described in example 1 and some non-critical
variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) :1176.21 (S02); 815,787(C-CI) Mass (m/z) : 379, 381 (M+H)+ ; 1H-NMR(5DDppm): 2.34 (s,6H); 2.72-2.78 (t,2H, J = 5.4 Hz); 4.01-4.10 (t, 2H, J = 5.4 Hz); 6.89 (s,1H); 7.16-7.26 (dd, 1H); 7.38-7.57 (m,4H); 7.78-7.82 (m, 2H); 8.02-8.03 (d,1H).
Example - 53 : [2-(1-(4'-lsopropyIbenzenesu(fonyl)-6-chloro-1H-indoI-3-
yloxy)ethyl]dimethyIamine
Using essentially the general procedure described in example 1 and some non-critical
variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR
spectra (cm'1) :1176.21 (S02);8151787(C-CI) Mass (m/z): 421, 423 (M+H)+;
Example - 54 : ^(l^'-Bromo^-methoxybenzenesulfonyO-e-chloro-IH-indol-S-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm'1) :1176.21 (S02); 815,787 (C-Ci) Mass (m/z): 487, 489, 491 (M+H)Example - 55 : [2-(1-(2,-Bromo-4'-methylbenzenesulfonyl)-6-chloro-1H-indol-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) ;1176.21 (S02); 815, 787 (C-CI) Mass (m/z): 471, 473, 475 (M+H)+.
Example - 56 : ^-(I^S^'-DimethoxybenzenesulfonylJ-S-chloro-IH-indol-S-
yioxy)ethyi]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1) :1176.21 (S02); 815,787 (C-CI) Mass (m/z): 439, 441 (M+H)+
Example - 57 : [2-(1-(4'-Bromobenzenesulfonyl)-6-chloro-1H-indoN3-yloxy)
ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared.
Melting range (°C) : Isolated as oil; IR spectra (cm'1) :1176.21 (S02); 815,787 (C-CI) Mass (m/z): 457, 459, 461 (M+H)+.
Example - 58 [2-(1 -(4'-Chlorobenzenesulfonyl)-6-chloro-1 H-indol-3-yloxy)
ethyl]dJmethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) :1176.21 (S02); 815, 787 (C-CI) Mass (m/z): 413, 415, 417 (M+H)+;
Example - 59 : [2-(1-(4'Fluorobenzenesulfonyl)-5-chJoro-1H-indol-3-yloxy)
ethyljdimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) : 1165; Mass (m/z) : 397, 399 (M+H)+; 1H-NMR (SDDppm) : 2.37 (s, 6H); 2.77-2.83 (t, 2H, J = 5.4 Hz); 4.06-4.12 (t, 2H, J = 5.4 Hz); 6.86 (s, 1H); 7.06-7.26 (m, 3H); 7.44-7.48 (d, 1H); 7.79-7.86 (m, 2H); 8.00-8.01 (d, 1H).
Example - 60 : [2-(1 -(2'Bromobenzenesulfonyl)-5-chloro-1 H-indol-3-yloxy)
ethyljdimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm'1): 1167; Mass (m/z): 457, 459, 461 (M+H)+;
Example - 61 : [2-(1-(4'-Methylbenzenesulfonyl)-5-chloro-1H-indol-3-yloxy)
ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm'1) :1173.4 (S02); 812,786 (C-CI); Mass (m/z) : 393, 395 (M+H)+; 1H-NMR (SjQppm): 2.35 (s, 9H, CH3and NMe2); 2.74-2.8 (t, 2H, J = 5.4 Hz); 4.05-4.10 (t, 2H, J = 5.4 Hz); 6.88 (s, 1H); 7.15-7.26 (m, 3H); 7.42-7.46 (d, 1H); 7.66-7.71 (d, 2H); 8.01-8.02 (d, 1H).
Example - 62 : [2-(1 -(Benzenesulfonyl)-5-chloro-1 H-indol-3-yloxy)
ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm'1) .-1176.21 (SO,); 815, 787 (C-CI) Mass (m/z): 379, 381 (M+H)+; 1H-NMR (5QDPpm): 2.34 (s, 6H); 2.72-2.78 (t, 2H. J = 5.4 Hz); 4.01-4.10 (t, 2H, J = 5.4 Hz); 6 89 (S n 7-16-7.26 (dd. 1H); 7.38-7.57 (m, 4H); 7.78-7.82 (m. 2H>; 8.02-8.03
(d,1H).
Example - 63 : [2-(1 -(4'-lsopropylbenzenesulfonyl)-5-Chloro-1 H-indol-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical
variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR
spectra (cm-1) :1176.21 (S02); 815,787 (C-CI); Mass (m/z): 421, 423 (M+H)+.
Example - 64 : [2-(1 -(2,-Bromo-4'-methoxybenzenesulfonyI)-5-chIoro-1 H-indol-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) :1176.21 (S02); 815,787 (C-CI); Mass (m/z): 487, 489, 491 (M+H)+.
Example - 65 : [2-(1-(2'-Bromo-4,-methyIbenzenesulfonyl)-5-chloro-1 H-indol-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) :1176.21 (S02); 815,787 (C-CI); Mass (m/z): 471, 473, 475 (M+H)Example - 66 : ^-(l-tS'^'-DimethoxybenzenesulfonyO-S-chioro-IH-indoi-S-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) :1176.21 (S02); 815,787 (C-CI); Mass (m/z) : 439 (M+H)+.
Example - 67 : [2-(1-(4'-Bromobenzenesulfonyl)-5-chloro-1H-indol-3-yloxy)
ethyljdimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) :1176.21 (S02); 815,787 (C-CI); Mass (m/z): 457, 459, 461 (M+H)+.
Example - 68 : ^-(l^-ChlorobenzenesulfonylJ-S-chloro-IH-indol-S-yloxy)
ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR
spectra (cm-1) :1176.21 (S02); 815,787 (C-CI); Mass (r-'z): 413, 4^5, 417 (M+H)+.
Example - 69 : [2-(1-BenzenesulfonyI)«5-chloro-2-phenyl-1H-indol-3-yloxy)
ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical
variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR
spectra (cm*1) :1176.21 (S02); 815, 787 (C-CI); Mass (m/z): 455, 457 (M+H)+.
Example - 70 : p-tl^'-Bromo-^-methylbenzenesulfonyO-S-chloro^-phenyl-l H-
indol-3-yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1) :1176.21 (S02); 815,787 (C-CI); Mass (m/z): 547, 549, 551 (M+H)+.
Example - 71 : ^-(l^'-FIuorobenzenesuIfonyO-S-chloro^-phenyl-IH-indoI-S-
yloxy)ethyl]dimethyiamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) ; Isolated as oil; IR spectra (cm*1) :1176.21 (S02); 815,787 (C-CI); Mass (m/z): 473, 475 (M+H)+.
Example - 72 : [2-(1-(Benzenesulfonyl)-5-chloro-2-methyl-1H-indol-3-yloxy)
ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm'1) :1176.21 (S02); 815,787 (C-CI); Mass (m/z): 393, 395 (M+H)+.
Example - 73 : [2-(1-(4TIuorobenzenesulfonyl)-5-chloro-2-methyl-1H-indol-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1) :1176.21 (S02); 815,787 (C-CI); Mass (m/z): 411, 413 (M+H)+.
Example - 74 : ^-(l^'-FIuorobenzenesulfonyO-SJ-dichloro-IH^indol-S-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR
spectra (cm-1) :1176.21 (S02); *15, 787 (C-CI); Mass (m/z) : 431, 433, 435 (M+H)+.
Example - 75 : [2-(1-(2'-Bromobenzenesulfonyl)-5J7-dichloro-1H-indol-3-
yioxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical
variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR
spectra (cm'1) :1176.21 (S02); 815, 787 (C-CI); Mass (m/z): 491, 493, 495 (M+H)+.
Example - 76 : [2-(1-(Benzenesulfonyl)-5,7-dichloro-1H-indol-3-yloxy)ethyI]
dimethylamine
Using essentially the general procedure described in example 1 and some non-critical
variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR
spectra (cm"1) :1176.21 (S02); 815, 787 (C-CI); Mass (m/z): 413, 415, 417 (M+Hf.
Example - 77 : [2-(1 -(Benzenesulfonyl)-5,7-dichloro-2-methyl-1 H-indoI-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm*1) :1176.21 (S02); 815, 787 (C-CI); Mass (m/z): 427, 429, 431 (M+H)+.
Example - 78 : ^-(l-BenzenesulfonyO-SJ-dichloro^-phenyl-IH-indol-S-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1) :1176.21 (S02); 815, 787 (C-CI): Mass (m/z) : 489f 491, 493 (M+H)+.
Example - 79 : ^-(l^'Methyl-BenzenesulfonyO-SJ-Dichloro^-Phenyl-IH-indol-
3-yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm'1) :1176.21 (S02); 815, 787 (C-CI); Mass (m/z): 503, 505, 507 (M+H)+.
Example - 80 : ^-(l^'-FluorobenzenesulfonylJ-S-chloro^-bromo-IH-indol-S-
yloxy)ethyl]dimethyIamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR
spectra (cm-1) :1176.21 (S02); 815, 787 (C-CI); Mass (m/z) : 475, 477, 479 (M+H)+.
Example - 81 : [2-(1-(4'-Chlorobenzenesulfonyl)-5-chloro-7-bromo-1H-indol-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) :1176.21 (S02); 815, 787 (C-CI); Mass (m/z): 491, 493, 495. Example - 82 : [2-(1-BenzenesuIfonyl)-5-Ch!oro-7-bromo-2-methyl-1H-indol-3-
yIoxy)ethyl]dimethylamine Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) :1176.21 (S02); 815, 787 (C-CI); Mass (m/z): 471, 473, 475 (M+H)+.
Example - 83 : ^-(l^'-Bromo^-methoxybenzenesuIfonyO-S-Chloro^-Bromo-
2-phenyl-1H-indol-3-yloxy)ethyl]dimethyIamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) :1176.21 (S02); 815, 787 (C-CI); Mass (m/z) : 641, 643, 645 (M+H)Example - 84 ; ^-(l^'-FluorobenzenesulfonyO-S-chloro^-bromo^-phenyMH-
indol-3-yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm'1) :1176.21 (S02); 815, 787 (C-CI); Mass (m/z) : 551, 553, 555 (M+H)+.
Example - 85 : [2-(1-(4'-Bromobenzenesulfonyl)-5-chloro-7-bromo-2-phenyl-1H-
indol-3-yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) :1176.21 (S02); 815, 787 (C-CI); Mass (m/z): 611, 613, 615 (M+H)+.
Example - 86 : [2-(1-Benzenesulfonyl)-5-methoxy-1H-indol-3-yloxy)ethyI]
dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm'1) :1176.21 (S02); Mass (m/z): 375.4 (M+H)+.
Example - 87 : [2-(1-(4'-BromobenzenesuIfonyl)-5-Methoxy-1H-indoI-3-yloxy)
ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical
variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR
spectra (cm-1) :1176.21 (S02) Mass (m/z): 453, 455 (M+H)+.
Example - 88 : [2-(1-(4'-Fluorobenzenesulfonyl)-5-Methoxy-1H-indol-3-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (crrf1) :1176.21 (S02); Mass (m/z): 393.4(M+H)+.
Example - 89 : P-fl^'-ChlorobenzenesulfonylJ-S-Methoxy-IH-indol-S-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm'1) :1176.21 (S02); Mass (m/z): 409, 411 (M+H)+.
Example - 90 : [2-{1-Benzenesulfonyl)-5-Methoxy-2-Methyl-1H-indol-3-yloxy)
ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm"1) :1176.21 (S02); Mass (m/z): 389.4 (M+H)T ■
Example - 91 : ^-(l^-FluorobenzenesulfonyO-S-Methoxy^-MethyMH-indoI-S-
yloxy)ethyl]dimethyIamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C) : Isolated as oil; IR spectra (cm-1) :1176.21 (S02); Mass (m/z): 407.4 (M+H)+.
Example - 92 : ^-(l^'-FluorobenzenesulfonyO-S-methoxy^-phenyl-IH-indol-S-
yloxy)ethyl]dimethylamine
Using essentially the general procedure described in example 1 and some non-critical variations, the above derivative was prepared. Melting range (°C): Isolated as oil; IR spectra (cm"1) :1176.21 (S02); Mass (m/z): 469.5 (M+H)+.
its stereoisomers, its radioisotopes, its geometric forms, its N-oxide, its polymorphs,
its pharmaceutical^ acceptable salts, its pharmaceutically acceptable solvates, its
useful bio-active metabolites, any suitable combination of the above,
wherein R1f R2, R3, RA, R5, Re, R7, Rs, R9, R10, R11 and R12 may be same or different,
and represent hydrogen, halogen, perhaloalkyl, hydroxy, thio, amino, nitro, cyano,
formyl, amidino, guanidino, substituted or unsubstituted groups selected from linear
or branched (CrCi2)alkyl, (CrC12)alkenyJ, (C2-C12)aikynyl, (C3-C7)cycloalkyl, (C3-
C7)cycloalkenyl, bicycloalkyl, bicycloaikenyl, (CrCi2)alkoxy, cycIo(C3-C7)alkoxy,
aryl, aryloxy, aralkyl, aralkoxy, heterocyclyl, heteroaryl, heterocyclylalkyl,
heteroaralkyl, heteroaryloxy, heteroarafkoxy, heterocyclylalkyloxy, acyl, acyloxy,
acylamino, monoalkylamino, dialkylamino, arylamino, diarylamino, aralkylamino,
alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, heterocyciylalkoxycarbonyl,
heteroaryloxycarbonyl, hydroxyalkyl, aminoalkyl, monoalkylaminoalkyl,
dialkylaminoalkyl, alkoxyalkyl arylalkyl, aralkoxyalkyl, alkylthio, thioalkyl,
alkoxycarbonylamino, aralkyloxycarbonylamino, aminocarbonylamino,
alkylaminocarbonylamino, alkylamidino, alkylguanidino, dialkylguanidino, hydrazino, hydroxylamino, carboxylic acid and its derivatives, sulfonic acids and its derivatives, phosphoric add and its derivatives; or the adjacent groups like R1 and R7 or R2 and R3 or R3 and R4 or R5 and R« or R6 and R7 or R7 and R8 or R0 and R9 together with carbon atoms to which they are attached may form a five or a six membered ring, optionally containing one or more double bonds and optionally containing one or more heteroatoms selected from O, N. S and combinations of double bond and heteroatoms; or R1t and R12 together with carbon atoms to which they are attached may form a three to a six membered rina. optionally containing one or more double
bonds and optionally containing one or more heteroatoms selected from O, N, S and combinations of double bond and heteroatoms;
R13 and R14 represents hydrogen, alkyl, aryl, aralkyl or together with nitrogen atom
form a cyclic three to seven membered ring, optionally, R13 and R14 together may
form a part of cyclic structure along with the intervening nitrogen; the heterocycle
may have either one, two or three double bonds; optionally it may also contain one
to three heteroatom selected from the group of oxygen, nitrogen and sulfur, and
includes ring fused with any carbocydic or heterocyclic ring, which can be saturated
or unsaturated; optionally, Rn and R13 together may form a part of cyclic structure
along with the intervening nitrogen and carbon atoms; the heterocycle may have
either one, two or three double bonds; optionally it may also contain one to three
heteroatom selected from the group of oxygen, nitrogen and sulfur, and includes
ring fused with any carbocydic or heterocyclic ring, which can be saturated or
unsaturated;
"n" is an integer ranging from 1 to 8, preferably 1 to 4, wherein the carbon chains which Hnw represents may be either linear or branched; and "mtt is an integer ranging from 0 to 2 preferably m is 1 or 2.
2. A compound according to Claim 1, which is selected from the following list:
[2-(1-(Benzenesulfonyl)-1H-indol-3-yloxy)ethyl]dimethylamine;
[2-(1-(4-lsopropylbenzenesulfonyl)-1l+-indol-3-yloxy)ethylJdimethylamine;
[2-(1-(2,-Bromo-4'-methoxybenzenesulfonyl)-1HHndol-3-yIoxy)ethyl]
dimethylamine;
^-(l^'^'-DimethoxybenzenesulfonyO-IH-indol-S-yloxyJethylJdimethylamine;
[2-{1-(4,-Bromobenzenesulfonyl)-1H-indol-3-yloxy)ethyl]dimethylamine;
[2-(1-(2,-Bromo-4'-Methylbenzenesulfonyl)-1H-indol-3-yloxy)ethyl] dimethylamine
[2-(1-(2,-Bromobenzenesulfonyl)-1H-indol-3-yloxy)ethyl]dimethylamine;
[2-(1-(4'-Fluorobenzenesulfonyl)-1H-indol-3-yloxy)ethyl]dimethylamine;
[2-(1-(4'-Chlorobenzenesulfonyl)-1H-indol-3-yloxy)ethyl]dimethylamine;
[2-(1-(4'-Methylbenzenesulfonyl)-1H-indol-3-yloxy)ethyl]dimethylamine;
[2-(1-(Benzenesulfonyl)-2-phenyl-1H-indol-3-yloxy)ethyl]dimethylamine;
^-(l^-lsopropylbenzenesulfonyO^-phenyl-IH-indol-S-yloxyJethyl]
dimethylamine; [2-(1-(2l-Bromo-4,-methoxybenzenesulfonyl)-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(2\4,-Dimethoxyben2enesuIfony!)-2-phenyl-1H-indol-3-yIoxy)ethyl] dimethylamine ;
[2-(1-(4,-Bromobnzenesu!fonyl)-2-phenyl»1H-indol-3-yloxy)ethyI]dimethylamine
[2-(1-(2'-Bromo-4,-Methy!ben2enesulfonyI)-2-phenyi-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(2'-Bromobenzenesu!fonyl)-2-phenyl-1H-indol-3-yloxy)ethyl]dimethylamine
[2-(1-{4,-Fluoroben2enesulfony))-2-phenyI-1H-indol-3-yloxy)ethyl]dimethylamine
[2-(1«(4'-Chlorobenzenesulfonyi)-2-phenyl«1H-indoi-3-yIoxy)ethyl]dimethyIam!ne
[2-(1-(4'-MethylbenzcnesuIfonyl)-2-phenyl-1H-indoI-3-yloxy)ethyl]dimethylamine
[2-(1-(Benzenesulfonyl)~ 2-methyM H-indol-3-yloxy)ethyl]dimethylamine;
[2-(1-(4MsopropylbenzenesulfonyQ- 2- methyl -1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(2,-Bromo-4'«methoxybenzenesulfonyl)- 2- methyl -1H-indol-3-yIoxy)ethyl]
dimethylamine ;
^-(l^'^'-DimethoxybenzenesulfonyO- 2- methyl -1H-indol-3-yloxy)ethyl]
dimethylamine;
(2-(1-(4'-Bromobenzenesulfonyl)- 2- methyl -1H-indol-3-yIoxy)ethyl]
dimethylamine;
[2-(1-(2'-Bromo-4,-MethylbenzenesuIfonyl)- 2- methyl -1H-indol-3-yloxy)ethyI]
dimethylamine;
[2~(1-(2'-BromobenzenesuIfonyl}- 2- methyl -1 H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(4'-FIuorobenzenesuIfonyl)- 2- methyl -1H-indol-3-yloxy)ethylJ
dimethylamine;
f2-(1-(4'-Chlorobenzenesulfonyl)- 2- methyl -1H-indol-3-y!oxy)ethyl]
dimethylamine;
[2-(1-(4'-Methylbenzenesulfonyl)-2- methyl -1H-indol-3-yloxy)ethyl] dimethylamine;
[2-(1-(Benzeneslfonyl)-5-bromo-1H-indol-3-yloxy)ethyl]dimethylamine;
[2-(1 -(4'-lsopropyIbenzenesulfonyl)- 5-bromo-1 H-indoI-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(2,-Bromo-4'-methoxybenzenesulfonyl)-5-bromo-1H-indol-3-yloxy)ethyl]
dimethylamine; [2-(1-(2,,4,-Dimethoxybenzenesulfonyl)-5-bromo-1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(4,-Bromobenzenesulfonyl)-5-bromo-1H-indol-3-yloxy)ethyl]dimethylamine [2-(1-(2,-Bromo-4,-Methylbenzenesulfonyl)-5-bromo-1H-indol-3-yloxy)ethyl] dimethylamine ;
[2-(1-(2,-BromobenzenesulfonyI)- 5-bromo-1 H-indol-3-yloxy)ethylj ^methylamine
[2-(1-(4'-Fluorobenzenesulfonyl)- 5-bromo-1H-indol«3-yioxy)ethyI]dimethyiamine
[2-(1 -(4'-Chlorobenzenesulfonyl)- 5-bromo-1 H-indol-3-yloxy)ethylj dimethylamine
[2-(1-(4,-Methylbenzenesulfonyl)-5-bromo-1H-indol-3-yloxy)ethyl] dimethylamine
[2-(1-(Benzenesulfonyl)- 5-bromo- 2-phenyi-1H-indoI-3-yloxy)ethyl] dimethylamine;
[2-(1-(4'-lsopropylbenzenesulfonyl)- 5-bromo- 2-phenyl-1 H-indol-3-yloxy)ethylj
dimethylamine ;
[2-(1-(2,-Bromo-4,-methoxybenzenesulfonyl)- 5-bromo- 2-phenyl-1 H-indol-3-yloxy)
ethyljdimethylamine;
^-(l-CZ^'-Dimethoxybenzenesulfonyl)- 5-bromo- 2-phenyl-1 H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(4'-Bromobenzenesulfonyl)-5-bromo-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(2-Bromo-4MVIethyIbenzenesulfonyl)- 5-bromo- 2-phenyl-1 H-indol-3-yloxy)
ethyljdimethylamine;
[2-(1-(2'-Bromobenzenesulfonyl)-5-bromo-2-phenyl-1H-indol-3-yloxy)ettiyl]
dimethylamine ; ^-(^(^-FluorobenzenesulfonyO-S-bromo^-phenyl-IH-indol-S-yloxyJethyl]
dimethylamine; [2-(1-(4,-Chlorobenzenesulfonyl)-5-bromo-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine; [2-(1-(4-Methylbenzenesulfonyl)-5-bromo-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine; [2-(1-(Benzenesulfonyl)-5-bromo-2-methyl-1H-indol-3-yloxy)ethyl]dimethylamine
[2-(1-(4'-lsopropylbenzenesulfonyl)- 5-bromo-2- methyl -1H-indol-3-yloxy)ethylj
dimethylamine;
[2-(1-(2'-Bromo-4'-methoxybenzenesuIfonyl)- 5-bromo- 2- methyl -1H-indol-3-
yloxy) ethyljdimethylamine;
[2-(1~(2\4'-Dimethoxybenzenesulfonyl)- 5-bromo-2- methyl -1H-indol-3-
yloxy)ethyljdimethylamine;
[2-(1-(4'-Bromobenzenesutfonyl)- 5-bromo-2- methyl -1H-indoI-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(2'-Dromo-4'-Melhylbenzenesulfonyl)- 5-bromo- 2- methyl -1H-indoI-3-
yloxy)ethyl]dimethylamine;
[2-(1-(2,-Bromobenzenesulfonyl)- 5-bromo-2- methyl ~1H-indol-3-yloxy)ethyij
dimethylamine ;
[2-(1-{4,-FluorobenzenesulfonyD- 5-bromo-2- methyl -1H-indol-3-yfoxy)ethyl] dimethylamine;
[2-(1-(4'-Chiorobenzenesulfonyl)- 5-bromo-2- methyl -1H-indoI-3-yIoxy)ethyI] dimethylamine;
[2-(1-(4'-Methylbenzenesulfonyl)- 5-bromo-2- methyl -1H-indol«3-yloxy)ethyl]
dimethylamine;
[2-(1-(Benzenesulfonyl)-6-chloro-1H-indol-3-yloxy)ethyl]dimethylamine;
[2-(1-(4'-lsopropylbenzenesulfonyl)-6-chloro-1H-indol-3«yloxy)ethyl]
dimethylamine;
[2-(1-(2'-Bromo-4,-methoxybenzenesulfonyl)-6-chloro-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(2,,4,-Dimethoxybenzenesulfonyl)-6-chloro-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(4'-Bromobenzenesulfonyl)-6-chloro-1H"indol-3-yloxy)ethyl]dimethylamine
[2-(1-(2,-Bromo^,-Methylbenzenesulfonyl)-6-chloro-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(2-Bromobenzenesulfonyl)-6-chloro-1H-indol-3-yloxy)ethyl]dimethylamine
[2-(1 -(4'-Fluorobenzenesulfonyl)- 6-chtoro-1 H-indol-3-yloxy)ethyI]dimethylamine
[2-(1-(4,-Chlorobenzenesuifonyl)-6-chloro-1l4-indol-3-yloxy)ethyl]dimethylamine
[2-(1 -(4'-MethylbenzenesulfonyI)- 6-chk>ro-1 H-indol-3-yIoxy)ethyI]dimethylamine
[2-(1-(Benzenesulfonyl)- 6-chloro- 2-phenyM H-indol-3-yloxy)ethyl]dimethylamine
(2'(1-(4'-l3opropylbenzenesuIfonyl)- 6-chloro- 2-phenyl-1 H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(2l-Bromo-4-methoxybenzenesulfonyl)- 6-chloro- 2-phenyl-1 H-indol-3-yIoxy)
ethyl]dimethylamine;
[2-(1-(2\4'-DimethoxybonzenesuIfonyi)- 6-chloro- 2-phenyl-1 H-indol-3-
yloxy)ethyl]dimethylamine;
[2-(1-(4,-Bromobenzenesulfonyl)-6-chloro-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(2'-Bromo-4'-MethylbenzenesuIfonyl)- 6-chloro- 2-phenyl-1 H-indoI-3-yloxy)
ethyl] dimethylamine;
[2-(1-(2,-Bromobenzenesulfonyl)-6-chloro-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine; [2-(1-(4'-Fluorobenzenesulfonyl)-6-chloro-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine ; [2-(1-(4'»Chlorobenzenesulfonyl)-6-chloro-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(4'-Methy!tc.nzenesulfo^ dimethylamine;
[2-(1-(Benzenesulfonyl)-6-chl6ro-2-methyl-lH-indol-3-yloxy)ethyl]dim
[2-(1-(4,-isopropylbenzenesulfonyl)- 6-chloro-2- methyl -1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(2'-Bromo-4,-methoxybenzenesulfonyl)- 6-chloro- 2- methyl -1H-indol-3-
yloxy) ethyl]dimethylamine ;
[2-(1-(2,,4,«Dimethoxybenzenesulfonyl)- 6-chIoro-2- methyl -1H-indol-3-yloxy)
ethyl] dimethylamine;
[2-(1-(4'-Bromobenzenesulfonyl)~ 6-chloro-2- methyl -1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2"(1-(2,-Bromo-4,*Methylbenzenesulfonyl)- 6-chloro- 2- methyl -1H-indol-3-yioxy)
ethyl] dimethylamine;
{2-(1-(2'-Bromobenzenesulfonyl)- 6-ch)oro-2- methyl -1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(4'-FluorobenzenesulfonyI)- 6-chloro-2- methyl -1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(4'-ChlorobenzenesulfonyI)- 6-chloro-2- methyl -1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(4'-MethylbenzenesuIfonyl)- 6-chloro-2- methyl -1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(Benzenesulfonyt)-5-chloro-1H-indol-3-yloxy)ethyl]dimethylamine;
[2»(1-(4,-lsopropylbenzenesulfonyl)- 5-chloro-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1 -(2,-Bromo-4,-methoxybenzenesulfonyl)- 5-ch!oro-1 H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1«(2,,4,-Dimethoxybenzenesulfonyl)-5-chloro-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(4l-Bromobenzenesulfonyl)-5-chloro-1H-indol-3-yloxy)ethyl]dimethyiamine
[2-(1-(2,-Bromo-4,-Methylbenzenesulfonyl)-5-chloro-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(2,-Bromobenzenesulfonyl)-5-chioro-1H-indol-3-y!oxy)ethyl]dimethylamine P-CI-C^-FluorobenzenesulfonyO-S-chloro-IH-indol-S-yloxyJethyndimethylamine [2-(1 -(4'-Chlorobenzenesulfonyl)- 5-chloro-1 H-indol-3-yloxy)ethyl]dimethyiamine [2-(1"(4'-Methylbenzenesulfonyl)»5-chloro-1H-indol-3-yloxy)ethyl]dimethylamine f2-(1-(Benzenesulfonyl)- 5-chloro- 2-phenyl-1 H-indol-3-yloxy)ethyl]dimethylamine
f2-(1-(4'-lsopropylben7enesulfonyI)- 5-chloro- 2 phcnyl-1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(2'-Bromo-4'-methoxybenzenesulfonyl)- 5-chloro- 2-phenyl-1 H-indol-3-yloxy)
ethyljdimethylamine ,
[2-(1 -(2\4'-Dimethoxybenzenesulfonyl)- 5-chloro- 2-phenyl-1 H-indol-3-yloxy)
ethyl]dimethylamine ;
[2-(1-(4'-Bromobenzenesulfonyl)-5-chloro-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(2,-Bromo-4,-Methylbenzenesulfonyl)- 5-chloro- 2-phenyl-1H-indol-3-yloxy)
ethyljdimethylamine ;
[2-(1-(2'-Bromobenzenesulfonyl)-5-chloro-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(4'-Fluorobenzenesulfonyl)-5-chloro-2'Phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine ;
{2-(1-(4,-Chlorobenzenesulfonyl)-5-diloro-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(4,-Methylbenzenesulfonyl)-5-chloro-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(Benzenesulfonyl)- 5-chloro-2-methyl-1H-indol-3-yloxy)ethyl]dimethylamine
[2-(1-(4'-lsopropyIbenzenesulfonyl)- 5-chloro-2- methyl -1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(2'-Bromo-4'-methoxybenzenesulfonyl)- 5-chloro- 2- methyl -1H-indol-3-
yloxy)ethyl]dimethylamine;
[2-(1-(2\4'-Dimethoxybenzenesulfonyl)- 5-chIoro-2- methyl -1H-indol-3-
yloxy)ethyl]dimethylamine;
[2-(1-(4'-Bromobenzenesuifonyl)- 5-chloro-2- methyl -1H-indol-3-
yloxy)ethyl]dimethylamine;
[2-(1-(2,-Bromo-4'-Methylbenzenesulfonyl)- 5-chloro- 2- methyl -1H-indol-3-yloxy)
ethyl] dimethylamine;
[2-(1-(2'-Bromobenzenesulfonyl)- 5-chloro-2- methyl -1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(4'-Fluorobenzenesulfonyl)- 5-ch!oro-2- methyl -1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(4'-Chlorobenzenesulfonyl)- 5-chloro-2- methyl -1H-indoI-3-y!oxy)ethyl]
dimethylamine;
[2-(1-(4'-Methylbenzenesulfony!)- 5-chloro-2- methyl -1H-indol-3-yloxy)ethyi]
dimethylamine;
[2-(1-(Benzenesulfonyi)-57-dichloro-1H-indoI-3-yloxy)ethyf)dimethylamine ; [2-(1-(4Msopropylbenzenesulfonyl)- 5J-dichloro-1H-indol-3-yloxy)ethyl] dimethylamine ;
[2-(1-(2'-Bromo-4'-methoxybenzenesulfonyl)-5,7-dichloro-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(2\4'-Dimethoxybenzenesulfonyi)-57-dichloro-1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1 -(4'-Bromobenzenesulfonyl)- 5,7-dichloro-1 H-indoI-3-yIoxy)ethyl]
dimethylamine ; [2-(1-(2,-Bromo-4,-Methylbenzenesulfonyl)-5I7-dichloro»1H-indol-3-yloxy)ethyl]
dimethylamine; [2-(1'(2,-Bromobenzenesulfonyl)-5,7-dichlaro-1H«indol-3-yloxy)ethyl]
dimethylamine;
[2-(1 -(4'-Fluorobenzenesutfonyl)- 5,7-dichloro-1 H-indol-3-yIoxy)ethyl]
dimethylamine ;
[2-(1-(4J-Chlorobenzenesulfonyl)-5I7-dichloro-1H-indol-3-yIoxy)ethyl]
dimethylamine ; [2-(1-(4,-Methylbenzenesulfonyl)-5l7-dichloro-1HHndol-3-yloxy)ethyl]
dimethylamine ; [2-(1-(Benzenesulfonyl)-5,7-dichloro-2-phenyl-1H-indoi-3-yloxy)ethyl]
dimethylamine ; [2-(1-(4'-lsopropylbenzenesulfonyl)-5,7-dichloro-2-phenyl-1H-indol-3-
yloxy)ethyl]dimethylamine;
[2-(1-(2,-Bromo-4,-methoxybenzenesulfonyl)- 5,7-dichloro- 2-phenyl-1 H-indol-3-
yloxy)ethyl]dimethylamine; [2-(1-(2,,4'-Dimethoxybenzenesulfonyl)-5,7-dichloro-2-phenyl-1H«indol-3-
yloxy)ethyl]dimethylamine; [2-(1-(4,-Bromobenzenesulfonyl)-5t7-dichloro-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2"(1-(2'-Bromo-4,-Methylbenzenesulfonyl)- 5,7-dichloro- 2-phenyM H-indol-3-
yloxy) ethyl]dimethylamine ;
[2-(1-(2'-Bromobenzenesulfonyl)- 5,7-dichloro-2-phenyM H-indol-3-yloxy) ethyl]
dimethylamine;
[2-(H4'-Fluorobenzenesulfonyi)- 5,7-dichloro-2-phenyI-1 H-indol-3-yloxy) ethyl]
dimethylamine ; ^(l-^'-ChlorobenzenesulfonyO-SJ-dichloro^-phenyMH-indol-S-yloxyJethyl]
dimethylamine;
[2-(1 -(4'-MethylbenzenesulfonyI)- 5,7-dichloro-2-phenyl-1 H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(Benzenesulfonyl)-57-dichloro-?-methyl-1H-indol-3^yloxy)ethyl]
dimethylamine ;
[2»(1-(4'-lsopropyIbenzenesulfonyl)- 5,7-dichloro-2- methyl -1H-indol-3-yloxy)
ethyl]dimethylamine;
[2-(1-(2'-Bromo-4^methoxybenzenesulfonyl)- 5,7-dichloro- 2- methyl -1H-indol-3-
yloxy)ethyl]dimethylamine;
[2-(1-(2\4,-Dimethoxybenzenesulfonyl)- 5,7-dich!oro-2- methyl -1H-indol-3-yloxy)
ethyl]dimethylamine;
P-CH^-Bromobenzenesulfonyl)- 5,7-dichloro-2- methyl -1H-indol-3-yloxy) ethyl]
dimethylamine;
[2-(1-(2,-Bromo,4,-Methylbenzenesulfonyl)- 5,7-dichloro- 2- methyl -1H-indol-3-
yloxy) ethyl]dimethylamine;
[2-(1-(2'-Bromobenzenesulfonyl)- 5t7-dichloro-2- methyl -1H-indol-3-yIoxy)
ethyl]dimethylamine;
[2-(1-(4,"Fluorobenzenesulfonyl)- 5,7-dichIoro-2- methyl -1H-indol-3-yloxy)
ethyl]dimethylamine;
[2-(1-(4'-ChIorobenzenesulfonyl)- 5,7-dichioro-2- methyl -1H-indol-3-yloxy)
ethyl]dimethylamine;
[2-(1-(4'-Methylbenzenesuffonyl)- 5,7-dichloro-2- methyl -1H-indol-3-yloxy)
ethyl]dimethylamine; [2-(1-(Benzenesulfonyl)-5,7-dibromo-1H-indol-3-yloxy)ethyl]dimethylamine
[2-(1-(4,-lsopropylbenzenesulfonyl)-5)7-dibromo-1H-indol-3-yloxy)ethyl]
dimethylamine; [2-(1-(2'-Bromo-4'-methoxybenzenesulfonyl)-5,7-dibromo-1H-indol-3-yloxy)ethyl]
dimethylamine ; [2-(1-(2,l4,-Dimethoxybenzenesulfonyl)«5J7-dibromo-1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(4'-Bromobenzenesulfonyl)- 5,7-dibromo-1H-indol-3-
yloxy)ethyl]dimethylamine; ^-(l^'-Bromo^-MethylbenzenesulfonyO-SJ-dibromo-IH-indol-S-yloxyJethyl]
dimethylamine ; [2-(1-(2'-Bromobenzenesulfonyl)-5t7-dibromo-1H-indol-3-yloxy)ethyl]
dimethylamine; [2-(1-(4,-Ruorobenzenesulfonyl)-5,7-dibromo-1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(4,-Chlorobenzenesulfonyl)-5)7-dibromo-1H-indol-3-yloxy)ethyl]
dimethylamine; [2-(1-(4,-Methylbenzenesulfonyl)-5,7-dibromo-1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(Benzenesulfonyl)- 5,7-dibromo- 2-phenyl-1 H-indoi-3-yloxy)ethyl]
dimethylamine;
[2-(1-(4'-lsopropyIbenzenesuIfonyI)- 5,7-dibromo- 2-phenyl-1 H-indol-3-
yloxy)ethyl]dimethylamine;
[2-(1-(2,-Bromo-4,-methoxybenzenesulfonyl)-5,7-dibromo-2-phenyl-1H-indol-3-
yloxy) ethyl] dimethylamine;
[2-(1-(2,l4,-Dimethoxybenzenesulfonyl)- 5,7-dibromo- 2-phenyl-1 H-indol-3-yloxy)
ethyl]dimethylamine; [2-(1-(4,-Bromobenzenesulfonyl)-5I7-dibromo-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(2,-Bromo-4,-Methylbenzenesulfonyl)- 5,7-dibromo- 2-phenyl-1 H-indol-3-
yloxy)ethyl]dimethylamine ;
[2-(1-(2,-Bromobenzenesulfonyl)-5,7-dibromo-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(4,-Fluorobenzenesulfonyl)-5,7-dibromo-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(4,-Chlorobenzenesulfonyl)-5l7-dibromo-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(4'-Methylbenzenesulfonyl)- 5,7-dibromo-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(Benzenesulfonyl)- 5,7-dibromo-2-methyl-1 H-indol-3-
yloxy)ethyl]dimethylamine;
^-(l-C^-lsopropylbenzenesulfonyl)- 5,7-dibromo-2- methyl -1H-indol-3-
yloxy)ethyl]dimethylamine;
[2-(1-(2'-Bromo-4,-methoxybenzenesulfonyl)- 5,7-dibromo- 2- methyl -1H-indol-3-
yloxy)ethyl] dimethylamine ;
[2-(1-(2\4'-Dimethoxybenzenesulfonyl)- 5.7-dibromo-2- methyl -1H-indol-3-yloxy)
ethyl] dimethylamine;
[2-(1-(4'-Bromobenzenesultonyl)- 5,7-dibromo-2- methyl -1H-indol-3-yloxy) ethyl]
dimethylamine ;
[2-(1-(2,-Bromol4,-Methylbenzenesulfonyl)- 5,7-dibromo- 2- methyl -1H-indol-3-
yloxy) ethyl]dimethylamine;
[2-(1-(2'-Bromobenzenesulfonyl)- 5,7-dibromo-2- methyl -1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(4'-FluorobenzenesuIfonyl)- 5,7-dibromo-2- methyl -1H-indol-3-yloxy)
ethyl]dimethylamine;
[2-(1-(4'-Chlorobenzenesuifonyl)- 5,7-dibromo-2- methyl -1H-indol-3-yloxy)
ethyljdimethylamine;
[2-(1-(4'-Methylbenzenesulfonyl)- 5,7-dibromo-2- methyl -1H-indol-3-yloxy)
ethyl]dimethylamine; [2-(1-(Benzenesulfonyl)-7-bromo-5-chloro-1H-indol«3-yloxy)ethyl]dimethylamine
[2-(1-(4,-lsopropylbenzenesulfonyl)-7-bromo-5-chloro-1H-indol-3-yloxy) ethyl]
dimethylamine; [2-(1-(2,-Bromo-4,-methoxybenzenesulfonyl)-7«bromo-5-chloro-1H-indol-3-yloxy)
ethyljdimethylamine;
[2-(1-(2\4'-Dimethoxybenzenesulfonyl)- 7-bromo-5-chloro-1 H-indol-3-yIoxy) ethyl]
dimethylamine; [2-(1-(4,-BromobenzenesulfonyO-7-bromo-5-chloro-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1 -(2,-Bromo-4'-Methylbenzenesulfonyl)- 7-bromo-5-chloro-1 H-indol-3-
yloxy)ethyl]dimethylamine; [2-(1-(2,-Bromobenzenesulfonyl)-7-bromo-5-chloro-1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(4'-FluorobGnzenesulfonyl)- 7-biurno-5«chloro-'IH-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(4,-Chlorobenzenesulfonyl)-7-bromo 5-chIoro-1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-( 1-(4'-Methylbenzenesulfonyl)-7-bromo-5-chloro-1 H-indol-3-yloxy)ethyl]
dimethylamine;
[2~(1-(Benzenesulfonyl)- 7~bromo-5-chIoro- 2-phenyl-1 H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(4'-lsopropylbenzenesulfonyl)- 7-bromo-5-chloro- 2-phenyl-1 H-indol-3-
yloxy)ethyl]dimethylamine ;
[2-(1-(2'-Bromo-4'-methoxybenzenesulfonyI)- 7-bromo-5-chloro- 2-phenyM H-
indol-3-yloxy)ethyl]dimethylamine ;
[2-(1-(2\4'-Dimethoxybenzenesulfonyl)- 7-bromo-5-chIoro- 2-phenyM H-indol-3-
yloxy)ethyl]dimethylamine; [2-(1-(4'-Bromobenzenesulfonyl)-7-bromo-5-chloro»2-phenyl-1H-indol-3-
yloxy)ethyl] dimethylamine ;
f2-(1-(2'-Bromo,4'-Methylbenzenesulfonyl)- 7-bromo-5-c;.;oro 2-pher,yMI l-indol-
3-yloxy)ethyl]dimethylamine ;
[2-(1-(2' Brornobenzenesulfanyl)- 7-bromo-5-chloro-2-ph«ny|.-1H indol-3-
yloxy)ethyl]dimethylamine;
[2-(1-(4'-Fluorobenzenesulfonyl)- 7-bromo-5-chloro-2-phenyl-1H-indol-3-yloxy)
ethyl]dimethylamine;
^-(l^^-ChlorobenzenesulfonyO^-bromo-S-chloro^-phenyi-IH-indol-S-yloxy)
ethyljdimethylamine ;
[2-(1-(4,-Methyibenzenesulfonyl)-7-bromo-5-chIoro-2-phenyI-1H-indo]-3-yloxy)
ethyljdimethylamine; [2-(1-(Benzenesulfonyl)-7-bromo-5-chloro«2»methyl-1H-indol-3«yloxy)ethyl]
dimethylamine ;
[2-(1-(4'-lsopropyIbenzene$ulfonyl)~ 7-bromo-5-chloro-2- methyl -1H-indol-3-
yloxy)ethyljdimethyIamine ;
f2-(1-(2-Bromo«4-methoxybenzenesulfonyl)- 7-bromo-5-chloro-2- methyl-1H-
indol-3-yloxy)ethyl]dimethylamine;
[2-(1-(2\4'-Dimethoxybenzenesulfonyl)- 7-bromo-5-chloro-2- methyl -1H-indol-3-
yloxy)ethyl]dimethylamine;
[2-(1-(4'-Bromobenzenesulfonyl)- 7-bromo-5-chloro-2- methyl -1H-tndol-3-yloxy)
ethyljdimethylamine;
{2-(1-(2,-Bromol4,-Methylbenzenesulfonyl)- 7-bromo-5-chloro- 2- methyl -1H-indol-
3-yloxy)ethylJdimethylamine;
{2-(1-(2,-Bromobenzenesulfonyl)- 7-bromo-5-chIoro-2- methyl -1H-indol-3-yloxy)
ethyljdimethylamine;
[2-(1-(4'-FluorobenzenesulfonyI)- 7-bromo-5-chloro-2- methyl -1H-indol-3-yloxy)
ethyljdimethylamine;
[2-(1-(4'-Chlorobenzenesulfonyl)- 7-bromo-5-chloro-2- methyl -1H-indol-3-yloxy)
ethyljdimethylamine;
[2-(1-(4'-Methylbenzenesulfonyl)- 7-bromo-5-chloro-2- methyl -1H-indol-3-yloxy)
ethyljdimethylamine;
[2-(1-(Benzenesulfonyl)-5-methoxy-1H-indol-3-yloxy)ethylJdimethylamine;
[2-(1«(4'-lsopropylbenzenesulfonyl)-5-methoxy«1H-indol-3-yloxy)ethylJ
dimethylamine;
[2-(1-(2,-Bromo-4'-methoxybenzenesulfonyl)- 5-methoxy-1 H-indol-3-yloxy) ethyl]
dimethylamine;
[2-(l'(2'r4,-Dimethoxybenzenesulfonyl)-5-methoxy-1H-indol«3-yloxy)ethyl]
dimethylamine ;
[2-(1-(4,-Bromobenzenesulfonyl)-5-methoxy-1H-indol-3-yloxy)ethyl]
dimethylamine ;
[2-(1-(2'-Bromo,4'-Methylbenzenesulfonyl)- 5-methoxy-1H-indoi-3-yloxy)ethyl]
dimethylamine ; [2-(1-(2'-Bromobenzenesulfonyl)-5-methoxy-1H-indoU3-yioxy)ethyl]
dimethylamine ; [2-(1-(4'-Fluorobenzenesulfonyl)-5-methoxy-1H-indol-3-yloxy)ethyl]
dimethylamine ; [2-(1-(4,-Chlorobenzenesulfonyl)-5-methoxy-1H-indol"3-yloxy)ethyl]
dimethylamine; [2-(1-(4'-Methylbenzenesulfonyl)-5-methoxy-1HHndol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(Benzenesuifonyl)- 5-methoxy- 2-phenyH H-indol-3-yIoxy)ethyl]
dimethylamine;
[2-(1-(4'-IsopropyibenzenesuIfonyi)- 5-methoxy- 2-phenyH H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(2,-Bromo-4,-methoxybenzenesulfonyl)- 5-methoxy- 2-phenyl-1 H-indol-3-
yloxy)ethyl]dimethylamine;
[2-(1-(2\4'-Dimethoxybenzenesulfonyl)- 5-methoxy- 2-phenyl-1 H-indol-3-
yloxy)ethyI]dimethylamine ;
[2-(1--(4,-Bromobenzenesulfonyl)-5-methoxy-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(2'-Bromo,4'-MethylbenzenesuIfonyl)*- 5-methoxy- 2-phenyl-1 H-indol-3-
yloxy)ethyl]dimethylamine;
[2-(1-(2,-Bromobenzenesulfonyl)-5-methoxy-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1 -(4'-Fluorobenzenesulfonyl)- 5-methoxy-2-pheny I-1 H-indoi-3-yloxy)ethyI]
dimethylamine ;
^-(l-C^-ChlorobenzenesulfonyO-S-methoxy^-phenyi-IH-indol-S-yioxyJethyl]
dimethylamine ;
[2-(1-(4'-MethylbenzenesulfonyI)- 5-methoxy-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(Benzenesulfonyl)-5-methoxy-2-methyl-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(4'-lsopropylbenzenesulfonyl)- 5-methoxy-2- methyl -1H-indol-3-yloxy)
ethyl]dimethylamine;
[2-(1-(2'-Bromo-4,-methoxybenzenesulfonyl)- 5-methoxy- 2- methyl -1H-indol-3-
yloxy)ethyl]dimethylamine ;
[2-(1-(2\4'-Dimethoxybenzenesulfonyl)- 5-methoxy-2- methyl -1H-indol-3-
yloxy)ethyl]dimethylamine ;
[2-(1-(4'-Bromobenzenesulfonyl)- 5-methoxy-2- methyl -1H-indol-3-yloxy)
ethyl]dimethylamine ;
[2-(1-(2'-Bromo,4'-Methylbenzenesulfonyl)- 5-methoxy- 2- methyl -1H-indol-3-
yloxy)ethyl]dimethylamine;
[2-(1-(2'-Bromobenzenesultonyl)- 5-methoxy-2- methyl-1H-indol-3-yloxy)
ethyl]dimethylamine;
[2-(1-(4'-Fluorobenzenesulfonyl)- 5-methoxy-2- methyl -1H-indoI-3-yloxy)
ethyl]dimethylamine;
[2-(1-(4'-Chlorobenzenesulfonyl)- 5-methoxy-2- methyl -1H-indol-3-yloxy)
ethyl]dimethylamine;
[2-(H4'~Methylbenzenesutfonyl)- 5-methoxy-2- methyl -1H-indol-3-yloxy)
ethyljdimethylamine;
[2-(1-Benzenesulfonyl-2«phenyl-1H-indol«3-yloxy)ethyl]dimethylamine;
[2-(1«Benzenesulfonyl-5-bromo-2«phenyl-1H-indol-3-yloxy)ethyl]dimethylamine;
[2-(1»Benzenesulfonyl-5-chloro-2-phenyl-1H-indol-3-yloxy)ethyl]dimethylamine;
[2-(1«Benzenesulfonyl-5-fluoro-2-phenyl-1H-indol-3«yloxy)ethyl]dimethylamine;
[2-(1«(2,«Bromobenzenesulfonyl)-2-phenyl-1H-indol-3-yloxy)ethyl]dimethylamine;
[2-(1-(4,-Methylbenzenesulfonyl)-5-fluoro-2-phenyl-1H-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-(4,-Methylbenzenesulfonyl)-5-chloro-2-phenyMH-indol-3-yloxy)ethyl]
dimethylamine;
[2-(1-Benzenesulfonyl-1H-indol-3-yloxy)ethyl]dimethylamine;
[2-(1-Benzenesulfonyl-5-bromo-1H-indol-3-yloxy)ethyl]dimethylamine;
[2-(1-Benzenesulfonyl-5-nitro-1H-indol-3-yloxy)ethyl]dimethylamine;
[2-(1-(2,-Bromobenzenesulfonyl)-1H-indol-3-yloxy)ethyl]dimethylamine;
[2-(1-(2,-Bromobenzenesulfonyl)-5-bromo-1H-indol-3-yloxy)ethyl]dimethylamine;
or a stereoisomer, or a polymorph, or any suitable combination of above such as a
nitrogen oxide thereof; a prodrug of the compound or the nitrogen oxide; a
pharmaceutically acceptable salt of the compound, the nitrogen oxide, or the
prodrug; or a solvate or hydrate of the compound, the nitrogen oxide, the prodrug
or the pharmaceutically acceptable salt.
3. A pharmaceutical composition comprising of one or more of a pharmaceutical^
acceptable carrier, diluent/s, excipient/s or solvates along with a therapeutically
effective amount of a compound according to Claim-1, its stereoisomers, its
geometric forms, its N-oxides, its polymorphs, its pharmaceutical^ acceptable
salts, or solvates.
4. A pharmaceutical composition according to Claim 3, in the form of a tablet,
capsule, powder, lozenges, suppositories, syrup, solution, suspension or
injectable, administered in, as a single dose or multiple dose units.
wherein R1( R2, R3, R4, R5, Re, R7. Rs, R9, Rio, R11 and R12 may be same or
different, and represent hydrogen, halogen, perhaloalkyl, hydroxy, thio, amino,
nitro, cyano, formyl, amidino, guanidino, substituted or unsubstituted groups
selected from linear or branched (CrCi2)alkyl, (C2-Ci2)all
Documents
Application Documents
| # |
Name |
Date |
| 1 |
0435-che-2007-form 5.pdf |
2011-09-02 |
| 1 |
435-CHE-2007_EXAMREPORT.pdf |
2016-07-02 |
| 2 |
0435-che-2007-form 3.pdf |
2011-09-02 |
| 2 |
435-CHE-2007 CORRESPONDENCE OTHERS 01-12-2011.pdf |
2011-12-01 |
| 3 |
0435-che-2007-form 1.pdf |
2011-09-02 |
| 3 |
435-CHE-2007 FORM-3 01-12-2011.pdf |
2011-12-01 |
| 4 |
0435-che-2007-abstract.pdf |
2011-09-02 |
| 4 |
0435-che-2007-description(complete).pdf |
2011-09-02 |
| 5 |
0435-che-2007-correspondnece-others.pdf |
2011-09-02 |
| 5 |
0435-che-2007-claims.pdf |
2011-09-02 |
| 6 |
0435-che-2007-claims.pdf |
2011-09-02 |
| 6 |
0435-che-2007-correspondnece-others.pdf |
2011-09-02 |
| 7 |
0435-che-2007-abstract.pdf |
2011-09-02 |
| 7 |
0435-che-2007-description(complete).pdf |
2011-09-02 |
| 8 |
0435-che-2007-form 1.pdf |
2011-09-02 |
| 8 |
435-CHE-2007 FORM-3 01-12-2011.pdf |
2011-12-01 |
| 9 |
0435-che-2007-form 3.pdf |
2011-09-02 |
| 9 |
435-CHE-2007 CORRESPONDENCE OTHERS 01-12-2011.pdf |
2011-12-01 |
| 10 |
435-CHE-2007_EXAMREPORT.pdf |
2016-07-02 |
| 10 |
0435-che-2007-form 5.pdf |
2011-09-02 |