MXPA00000890A - Indole compounds as cox-2 inhibitors - Google Patents

Abstract

This invention provides a compound of formula (I) and the pharmaceutically acceptable salts thereof, wherein L is oxygen or sulfur;Y is a direct bond or C1-4 alkylidene;Q is C1-6 alkyl, C3-7 cycloalkyl, phenyl, naphthyl, heteroaryl or the like;R1 is hydrogen, C1-6 alkyl or the like;R2 is hydrogen, C1-4 alkyl, C(O)R5 wherein R5 is C1-22 alkyl or C2-22 alkenyl, halosubstituted C1-8 alkyl, halosubstituted C2-8 alkenyl, -Y-C3-7 cycloalkyl, -Y-C3-7 cycloalkenyl, phenyl, naphthyl, heteroaryl or the like;X is halo, C1-4 alkyl, hydroxy, C1-4 alkoxy or the like;and n is 0, 1, 2 or 3, with the proviso that a group of formula -Y-Q is not methyl or ethyl when X is hydrogen;L is oxygen;R1 is hydrogen;and R2 is acetyl. This invention also provides a pharmaceutical composition useful for the treatment of a medical condition in which prostaglandins are implicated as pathogens. The indole compounds of the present invention exhibit inhibition of COX activity. Preferably compounds of this invention exhibit inhibitory activity against COX-2, with more preferable compounds having COX-2 selectivity.

Description

INDOL COMPOUNDS AS ANTI-INFLAMMATORY / ANALYZES AGENTS TECHNICAL FIELD This invention relates to novel inhibitors of cyclooxygenase. The compounds of this invention inhibit the biosynthesis of prostaglandins by intervening the action of the enzyme cyclooxygenase on arachidonic acid and, therefore, are useful in the treatment or alleviation of inflammation and other disorders associated with it. inflammation in mammals. This invention also relates to pharmaceutical compositions comprising such compounds.

BACKGROUND TECHNIQUE 15 Non-steroidal anti-inflammatory drugs (NSAIDs) are widely used in the treatment of pain and the signs and symptoms of artptis, due to their analgesic and anti-inflammatory activity. It is accepted that common NSAIDs act by blocking the activity of the cyclo-oxygenate (COX), also known as prostaglandin G / H synthase (PGHS), the enzyme that converts arachidonic acid into prostaglandin E2 (PGE2), which is the predominant eicosanoid detected in inflammatory conditions, are mediators of pain, fever and of other symptoms associated with inflammation. The inhibition of prostaglandin biosynthesis has been a therapeutic target for the discovery of anti-inflammatory drugs. However, the therapeutic use of conventional NSAIDs is limited mf due to the side effects associated with the drug, including life-threatening ulceration and renal toxicity. An alternative for NSAIDs is the use of corticosteroids, however, a long-term therapy can also produce serious side effects. Recently, two forms of COX were identified, a constitutive isoform (COX-1) and an inducible isoform (COX-2), whose expression is positively regulated at sites of inflammation (Vane, JR, Mitchell, JA, Appleton, I Tomlinson, A., Bishop-Bailey, D., Croxtoll, J., Willoughby, DA Proc. Nati, Acad. Sci. USA, 1994, 91, 2046). It is believed that COX-1 plays a physiological role and that it is responsible for gastrointestinal and renal protection. On the other hand, COX-2 seems to play a role pathological and be the predominant isoform present in inflammatory conditions. In several human disease states, which include rheumatoid arthritis and osteoarthritis, pyrexia, asthma, bone resorption, cardiovascular diseases, nephrotoxicity, atherosclerosis, hypotension, shock, pain, cancer and Alzheimer's disease, a paper pathological for prostaglandins. The NSAIDs currently present in the market inhibit the two isoforms of COX with a small variation of the selectivity, explaining their beneficial effects (inhibition of COX-2) and harmful effects (inhibition of COX-1). It is believed that the compounds that selectively inhibit the biosynthesis of prostaglandins by intervening the induction phase of the inducible cyclo-oxygenate-2 enzyme and / or by intervening the activity of the enzyme cyclo-oxygenase-2 on arachidonic acid , could provide an alternative therapy to the use of NSAIDs or corticosteroids, since such compounds would exert anti-inflammatory effects without the adverse side effects associated with the inhibition of COX-1. A variety of indole compounds are known and described in several patent applications. Specifically, international publications numbers WO 96/37467 and WO 96/37469 describe N-benzylindole compounds as inhibitors of cyclooxygenase-2. Also, in Khím. Geterotsikl. Soedin 1990, 11, 1569, by Tolkunov et al., A variety of indole compounds are described.

BRIEF DESCRIPTION OF THE INVENTION The present invention provides a compound of the following formula: (I) and pharmaceutically acceptable salts thereof, wherein L is oxygen or sulfur; And is it a direct bond or an alkylidene C? _4; Q is (a) C 1-6 -alkyl or haloalkyl-substituted C 1-6 alkyl, said alkyl being optionally substituted with up to three substituents independently selected from hydroxy, C 1-, -alkoxy, amino and mono- or di- (C- alkyl-? _) amino, (b) C3.7 cycloalkyl optionally substituted with up to three substituents independently selected from hydroxy, C 1-4 alkyl and C 1-4 alkoxy, (c) phenyl or naphthyl, said phenyl or naphtyl being optionally substituted with 10 to four substituents independently selected from (c-1) halo, C alquilo _ alkyl, halo-substituted C alquilo? alquiloalkyl, hydroxy, C alco _ alkoxy, halo-substituted C alco _ alkoxy, S (O) mR 3, SO 2 NH 2, SO 2 N (C-alkyl) ? _) 2, amino, mono- or di- (alkyl C? _4) amino, NHSO2R3, NHC (O) R3, CN, CO2H, CO2 (alkyl d-4), alkyl C? _4-OH, alkyl C ^ -OR3, CONH2, CONH (C-alkyl, 4), CON (C15 alkyl) 2 and OY-phenyl, said phenyl being optionally substituted with one or two substituents independently selected from halo, C alquilo alkyl; , • CF3, hydroxy, OR3, S (O) mR3, amino, mono- or di- (alkylC?) Amino and CN, (d) a monocyclic aromatic group of 5 atoms, said aromatic group having a heteroatom selected from O , S and N and that contains Optionally up to three N atoms in addition to said heteroatom, and said aromatic group being substituted with up to three substituents independently selected from (d-1) halo, C alquilo _ alkyl, C?-Halo-substituted alkyl, hydroxy, alkoxy CM, halosubstituted C1-4 alkoxy, C C4-4alkyl OH, S (O) mR3, SO2NH2, SO2N (C4-4alkyl) 2, amino, mono- or di- (C C4alkylamino) amino, NHSO2R3, NHC (O) R3, CN, CO2H, CO2 (C? _4 alkyl), C ^ -OR3 alkyl, CONH2, CONH (C? _4 alkyl), CON (C ^ 4 alkyl) 2, phenyl and phenyl mono-, di - or tri- substituted, wherein the substituent is independently selected from halo, CF3, C1-4 alkyl, hydroxy, C17 alkoxy. 4, OCF3, SR3, SO2CH3, SO2NH2, amino, C1.4 alkylamino and NHSO2R3, (e) a monocyclic aromatic group of 6 atoms, said aromatic group having a heteroatom which is N and optionally containing up to three atoms in addition to said heteroatom , and said aromatic group being substituted with up to three substituents independently selected from the above group (d-1); R 1 is hydrogen or C 1-6 alkyl optionally substituted with a substituent independently selected from hydroxy, OR 3, nitro, amino, mono- or di- (C 1 amino alkyl, CO 2 H, CO 2 (C 1-4 alkyl), CONH 2, CONH (alkyl d_4) and CON (alkyl 1-4) 2; R 2 is (a) hydrogen, (b) C 1-4 alkyl, (c) C (O) R 5, where R 5 is selected from (c-1) C? _22 alkyl or C2.22 alkenyl, said alkyl or alkenyl being optionally substituted with up to four substituents independently selected from (c-1-1) halo, hydroxy, OR3, S (O) mR3, nitro, amino, mono- or di- (alkyl) C? _4) amino, NHSO2R3, CO2H, CO2 (C1.4 alkyl), CONH2, CONH (alkyl) IÉ &JÜ.dLF'Ti C? _4), WITH (C? _4) 2 alkyl, naphthyl, and the groups of the following formulas: (c-2) C-_ 22 alkyl or C2_22 alkenyl) said alkyl or alkenyl being optionally substituted with five to forty-five halogen atoms, (c-3) -Y-cycloalkyl C3_ or -Y-cycloalkenyl C3_7, said cycloalkyl or cycloalkenyl optionally substituted with up to three substituents independently selected from (c-3-1) C 1-4 alkyl, hydroxy, OR 3, S (O) mR 3, amino, mono- or di- (C 1-4 alkyl) amino, CONH 2, CONH (alkyl d4) and CON (Cufe alkyl, (c-4) phenyl or naphthyl, said phenyl or naphthyl being optionally substituted with up to seven (preferably up to seven) substituents independently selected from (c-4-1) halo, C- alkyl ? 8, alkyl C? _4-OH, hydroxy, Ci-β alkoxy, halo-substituted C? _8 alkyl, halo-substituted C? _8 alkoxy, CN, nitro, S (O) mR3, SO2NH2, SO2NH (C1-4 alkyl), SO2N (C 4 alkyl) 2, C 1-4 amino alkylamino, di- (alkyl d- ^ amino, CONH 2, CONH (C 1-4 alkyl), CON (C 1) alkyl, OC (O) R 3 and optionally substituted phenyl with up to three its Selected participants independently between halo, C-M alkyl, hydroxy, OCH3, CF3) OCF3, CN, nitro, amino, mono- or di- (C1.4 alkyl) amino, CO2H, CO2 (alkyl d4) and CONH2. (c-5) a monocyclic aromatic group as defined in (d) and (e) above, said aromatic group being optionally substituted with up to three substituents independently selected from (c-5-1) halo, alkyl d_8, alkyl C? _4-OH, hydroxy, alkoxy ds, CF3, OCF3, CN, nitro, S (O) mR3, amino, mono- or di- (alkyl C? .4) amine, CONH2, CONH (alkyl d-4) , CON (alkyl 1-4) 2, CO2H and CO2 (C 1-4 alkyl), and -Y-phenyl, said phenyl being optionally substituted up to three substituents independently selected from halogen, C 1-4 alkyl, hydroxy, C 1-4 alkoxy , CF3, OCF3 > CN, nitro, S (O) mR3, amino, mono- or di- (alkyl d ^ amino, CO2H, CO2 (alkyl d_4), CONH2, CONH (alkyl d.4) and CON (C1 alkyl) 2, (c -6) a group of the following formula: X is halo, C 1 -4 alkyl, hydroxy, C 1-4 alkoxy, halo-substituted C 1-4 alkoxy, S (O) mR 3, amino, mono- or di- (C 1-4 alkyl) amino, NHSO 2 R 3, nitro, C 1 - alkyl 4 substituted halogen, CN, CO2H, CO2 (C? _4 alkyl), C? _4-OH alkyl, C1.4-alkyl, OR3, CONH2, CONH (C1-4 alkyl), or CON (C ^ alkyl, R3 is C1 alkyl .4 or halo-substituted C1-4 alkyl, m is 0.1, 2, n is 0, 1, 2 or 3, p is 1, 2, 3, 4 or 5, and q is 2 or 3; Z is oxygen, sulfur or NR4; And R4 is hydrogen, C6_6 alkyl, halo-substituted C4_4 alkyl or -Y-phenyl, said phenyl being optionally substituted with up to two substituents • independently selected from halo, C1-4alkyl, hydroxy, C1-4alkoxy, 5S (O) mR3, amino, mono- or di- (d-amino alkyl, CF3, OCF3t CN and nitro; with the proviso that a group of formula -YQ is not methyl or ethyl when X is hydrogen, L is oxygen, R1 is hydrogen, and R2 is acetyl, and the indole compounds of the present invention exhibit inhibition of COX activity. The invention has inhibitory activity against COX-2, the most preferable compounds having selectivity for COX-2. Accordingly, the present invention also provides a pharmaceutical composition useful for the treatment of a medical condition in which prostaglandins are implicated. Pathogens, comprising a compound of the formula (I): wherein L, Y, X, Q, R1, R2, R3, R4, R5, m, n, p, q and z are as defined above, and pharmaceutically acceptable salts thereof. invention provides a method for the treatment of a medical condition in which the Prostaglandins as pathogens, in a mammalian subject, comprising administering to said subject a therapeutically effective amount of said pharmaceutical composition. Medical conditions in which prostanglandins are implicated as pathogens include relief of pain, fever, and inflammation from a variety of conditions, including rheumatic fever, symptoms associated with influenza or other viral infections, cold • common, lumbar and cervical pain, dysmenorrhea, headache, toothache, sprains 5 and strains, myositis, neuralgia, synovitis, arthritis, including rheumatoid arthritis, joint degenerative diseases (osteoarthritis), gout and ankylosing spondylitis, bursitis, burns and injuries subsequent to surgical and dental procedures. The compounds and the pharmaceutical composition of this invention • 10 can inhibit neoplastic transformations in cells and the metastatic growth of tumors and, therefore, can be used in the treatment of cancer. The compounds and the pharmaceutical composition of this invention were used in the treatment and / or prevention of proliferation disorders mediated by cyclo-oxygenase, such as those that appear in diabetic retinopathy and in tumor angiogenesis. The compounds and the pharmaceutical composition of this invention can be useful in the treatment of dysmenorrhea, premature delivery, asthma and eosinophil-related disorders, in the treatment of Alzheimer's disease and in the treatment of bone loss 20 (treatment of osteoarthritis), for its ability to inhibit smooth muscle contraction induced by prostanoids by inhibiting the synthesis of contractile prostanoids. In addition, such compounds and pharmaceutical compositions that show specificity for COX-2 with respect to COX-1 will prove to be useful as an alternative to conventional NSAIDs, particularly in cases where such NSAIDs are contraindicated, such as in patients with peptic ulcers, gastritis, regional enteritis, ulcerative colitis, diverticulitis or with a recurrent history of Gl lesions, Gl hemorrhages, coagulation disorders, including anemia such as hypoprotombinemia, hemophilia or other bleeding problems; kidney diseases; before the anticoagulant surgery.

• DETAILED DESCRIPTION OF THE INVENTION As used herein, "halo" is fluoro, chloro, bromo or iodo. As used herein, the term "alkyl" means straight or branched chain saturated radicals of 1 to 22 carbon atoms, including, but not limited to, methyl, ethyl, n-propyl, isopropyl, n- • butyl, / so-butyl, secondary butyl, tertiary butyl, pentyl, hexyl, octyl, nonyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, eicosyl and the like. As used herein, the term "alkyl" "substituted" refers to an alkyl radical as described above, substituted with one or more halogens including, but not limited to, chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trichloroethyl, and the like.

"* R As used herein, the term" alkenyl "means straight or branched chain unsaturated radicals of 2 to 22 carbon atoms, including, but not limited to, 1-ethenyl, 1-propenyl, 2-propenyl, -butenyl, 2-butenyl, 2-methyl-1-propenyl and the like. As used herein, the term "cycloalkyl" means carbocyclic radicals of 3 to 8 carbon atoms, including, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. As used herein, the term "cycloalkenyl" means unsaturated carbocyclic radicals of 3 to 8 carbon atoms, including, but not limited to, cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, and the like. As used herein, a monocyclic aromatic group of 5 atoms (in the ring), usually has a heteroatom selected from O, S and N (in the ring). In addition to said heteroatom, the monocyclic aromatic group optionally may have up to three N (it's the ring) For example, the 5-atom monocyclic group includes thienyl, furyl, thiazolyl (for example, 1,3-thiazolyl), imidazolyl, pyrrolyl, oxazolyl (for example, 1,3-oxazolyl or 1,2-oxazolyl), thiazolyl ( for example, 1,2-thiazolyl), pyrazolyl, tetrazolyl, triazolyl (for example 1,2,3-triazolyl or 1,4-triazolyl), oxadiazolyl (for example 1,2,3-oxadiazolyl), thiadiazolyl (eg, 1,4-thiadiazolyl), isothiazolyl and the like. As used herein, a monocyclic aromatic group of 6 atoms (in the ring) normally has a heteroatom which is N (in the ring). In addition to said heteroatom, the monocyclic aromatic group may optionally have up to three N atoms (in the ring). For example, the monocyclic group of 6 atoms includes pyridyl, pyrazinyl, • pyrimidinyl, pyridazinyl, triazinyl (for example, 1, 3,5-triazinyl), tetrazinyl and 5 similar. Preferred compounds of this invention are those of the formula (I) wherein Y is a direct bond, methylene or ethylene; Q is (a) C 1-6 alkyl or halo-substituted C 1-6 alkyl, said • alkyl optionally substituted with up to two substituents independently selected from hydroxy, C 1-4 alkoxy, amino and mono- or di- (C 1-4 alkyl) amino, (b) C 3-7 cycloalkyl optionally substituted with up to two substituents independently selected from hydroxy, C 1-4 alkyl and C 1-4 alkoxy, 15 (c) phenyl or naphthyl, said phenyl or naphthyl being optionally substituted with up to four substituents independently selected from (c-1) halo, C 1-4 alkyl, C -4 alkyl halo-substituted, hydroxy, C 1-4 alkoxy, halo-substituted C 1-4 alkoxy, S (O) mR 3, SO 2 NH 2, SO 2 N (C 1-4 alkyl) 2. amino, 20 mono- or di- (C 4 alkyl) amino, NHSO 2 R 3, NHC (O) R 3, CN, CO 2 H, CO 2 (C 1 -4 alkyl), C 1 4 alkyl-OH, C 1 4 alkyl-OR 3 , CONH2, CONH (C1.4 alkyl), CON (C4_4) alkyl2 (d) a monocyclic aromatic group of 5 atoms, said aromatic group having a heteroatom selected from O, S and N and optionally containing N in addition to said heteroatom, and said aromatic group being substituted with up to three substituents independently selected from (d-1) halo, C 1-4 alkyl, halo-substituted C 1-4 alkyl, hydroxy, C 1-4 alkoxy, halo-substituted d-4-alkoxy , S (O) mR3, SO2NH2) SO2 N (amino alkyl, mono- or di- (alkylC? 4) amino, NHSO2R3) NHC (0) R3, CN, CO2H, CO2 (C1.4 alkyl), alkyl d-4-OH, C1-C3 alkyl, NHC (O) R3, CONH2) CONH (C-alkyl), CON (C4-4 alkyl) 2, phenyl and mono-, di- or tri- substituted phenyl, where the substituent is independently selects halo, CF3, C? _4 alkyl, Hydroxy, C1.4 alkoxy, OCF3, SR3, SO2CH3, SO2NH2, amino, mono- or di- (C4-4 alkyl) amino and NHSO2R3, (e) a monocyclic aromatic group having 6 atoms, said aromatic group having one heteroatom which is N and optionally containing one or two N atoms in addition to said heteroatom, and said group being aromatic substituted with up to three substituents independently selected from the above group (d-1); R1 is hydrogen or C6-6alkyl optionally substituted with a substituent independently selected from hydroxy, OR3, nitro, amino, mono- or di- (C4-4alkyl) amino and CO2H; R 2 is (a) hydrogen, (b) C 1-4 alkyl, (c) C (O) R 5, where R 5 is selected from (c-1) C 1 7 alkyl or C 2 7 alkenyl, said alkyl being 'X / r. ? "" < -. ' .. - «« - AS. r. £ z ,, ~? ... -. "- JE,. ... - ....,) .- _ -. -_a-B-_fta_ß_s ^ _-_ K-- <? - Alkenyl optionally substituted with up to four substituents independently selected from (c-1-1) halo, hydroxy, OR3, S (O) mR3, nitro, amino, mono- or di-; • (C 4 alkyl) amino, NHSO 2 R 3, CO 2 H, CO 2 (C 1 4 alkyl), CONH 2, CONH (C 5 alkyl 4), CON (C 4 alkyl) 2, OC (O) R 3 and the groups of the following formulas: • 10 (c-2) alkyl C? -? or C2-17 alkenyl, said alkyl or alkenyl being optionally substituted with five to twenty halogen atoms, (c-3) -Y-cycloalkyl C3.7 or -Y-cycloalkenyl C3_7, said cycloalkyl or cycloalkenyl being optionally substituted with a substituent independently selected from C alquilo _ alkyl, hydroxy and OR 3, 15 (c-4) phenyl or naphthyl, said phenyl or naphthyl being optionally substituted with up to three independently selected substituents • between halo, C? _8 alkyl, C 1-4 alkyl-OH, hydroxy, C? _8 alkoxy, halo-substituted C? _8 alkyl, halogenated C? _8 alkoxy, CN, nitro, amino and mono- or di- (C alkyl? _4) amino, 20 (c-5) a monocyclic aromatic group as defined in (d) and (e) above, said aromatic group being optionally substituted with up to three substituents independently selected from halo, C? _8 alkyl, C1- alkyl 4-OH, hydroxy, C 1 8 alkoxy, CF 3, OCF 3, CN, nitro, amino and mono- or di- , r ._, 3 as_fi-s, (C 1 -) alkyl amino, (c-6) tetrahydrofuryl, tetrahydropyrrolyl, tetrahydrothienyl or 1-methyl-tetrahydropyrrolyl; X is halo, C 1-4 alkyl, hydroxy, C 1-4 alkoxy, halo-substituted C 1-4 alkoxy, amino, mono- or di- (C 1-4 alkyl) amino, NHSO.sub.2 R 3, nitro, halo-substituted C 1-4 alkyl, CN or C02H; and R3 is C1-4alkyl or haloalkyl substituted C1-4alkyl. Further preferred compounds of this invention are those of the formula (I) wherein L is oxygen; And it's a direct link or methylene; Q is (b) C3.7 cycloalkyl optionally substituted with C? Alkyl? • 10 4 or C 1-4 alkoxy, (c) phenyl or naphthyl, said phenyl or naphthyl optionally substituted with up to three substituents independently selected from (c-1) halo, C 1-4 alkyl, halo-substituted C 1-4 alkyl, hydroxy, C 1 alkoxy, halo substituted C.sub.4 alkoxy, amino, mono- or di (alkyl d4) amine, CN, CO2H, and-SR3, • (d) a monocyclic aromatic group having 5 atoms, said aromatic group having a heteroatom selected from O, S and N and optionally containing an N atom in addition to said heteroatom, and said aromatic group substituted with up to three substituents independently selected from (d-1) halo, C 1-4 alkyl, halo-substituted C 1-4 alkyl, hydroxy, C 1-4 alkoxy, halo-substituted C 1-4 alkoxy, amino, mono- or di- ( C 1-4 alkyl) amino and C 1 alkyl (e) a monocyclic aromatic group of 6 atoms, said aromatic group having a heteroatom which is N and optionally containing • N atom other than said heteroatom, and said aromatic group being substituted with up to three substituents independently selected from the above group (d-1); R1 is hydrogen or C? _ Alkyl; R2 is (a) hydrogen, (c) C (O) R5, where R5 is selected from • 10 (c-1) C? -8 alkyl or C2-8 alkenyl > said alkyl or alkenyl being optionally substituted with up to three substituents independently selected from (c-1-1) halo, hydroxy, OR 3, SOR 3, nitro, amino, mono- or di- (C 1 .4) alkyl amino, NHSO 2 R 3, CO 2 H , CO2 (C 1-4 alkyl), CONH 2, CONH (C 1-4 alkyl), CON (C? 4 alkyl) 2, OC (O) R 3, (c-2) C? _8 alkyl or C2_8 alkenyl, said alkyl or alkenyl optionally substituted with five to seventeen halogen atoms, • (c-3) -Y-cycloalkyl C3.7 or -Y- C3.7 cycloalkenyl, said cycloalkyl or cycloalkenyl being optionally substituted with a substituent independently selected from C alquilo _ alkyl, hydroxy and OR3, 20 (c-4) phenyl optionally substituted with up to three substituents independently selected from halo, C 1 and hydroxy, (c-5) heteroaryl selected from pyridyl, quinolyl, thienyl, thiazolyl pyrimidyl and indolyl, said heteroaryl being optionally substituted with up to two substituents independently selected from halo, C 1-4 alkyl, hydroxy, C 1-4 alkoxy and CF 3, (c-6) tetrahydrofuryl or tetrahydrothienyl; X is halo, C 1-4 alkyl, hydroxy, C 1-4 alkoxy, amino, nitro or CN; and R3 is C3_3 or CF3 alkyl. Other preferred compounds of this invention are those of formula (I) wherein Y is a direct bond; Q is phenyl, cyclohexyl optionally substituted with methyl, ethyl or methoxy, or a monocyclic aromatic group selected from pyridyl, • pyrazinyl, thienyl, furyl, thiazolyl, imidazolyl and pyrrolyl, said phenyl or aromatic group being optionally substituted with up to two substituents independently selected from halo, methyl, methoxy, amino and hydoxymethyl, R 1 is hydrogen or methyl; R2 is (a) hydrogen. (c) C (O) R5, where R5 is selected from • (c-1) C6_6 alkyl optionally substituted with up to two substituents independently selected from hydroxy, OR3, SOR3, nitro, amino, mono- or di- (alkyl) C? -4) amino, NHSO2R3, CO2H, CO2 (C1.4 alkyl), CONH2, CONH (C1-4 alkyl), CON (C14 alkyl) 2, OC (O) R3 and phenyl, (c-2) trifluoromethyl or trichloromethyl, (c-3) cyclopropyl or cyclohexyl, (c-4) phenyl or halophenyl, (c-5) thienyl, (c-6) tetrahydrofuryl; X is chlorine, fluoro or cyano; and R3 is methyl, ethyl, propyl or CF3.

• Other preferred compounds of this invention are those of the formula (I) wherein Y is a direct bond; Q is phenyl, 3-methoxyphenyl, 3-methylphenyl, 2-chlorophenyl, 3-chlorophenyl, 3-bromophenyl, 2-pyridyl, 4-chloro-2-pyridyl, 4-methyl-2-pyridyl, 4-methoxy-2- pyridyl, 2-pyrazinyl, cyclohexyl, 3-methyl-cyclohexyl, 3-NH2-phenyl, 3-methylcyclohexyl, 3-hydroxymethyl-2-furyl or 3-fluorophenyl; R1 is hydrogen or methyl; R2 is hydrogen, CH3-C (O) -, (CH3) 2-C (O) -, phenyl-C (O) -, C2H5-C (O) -, C3H7-C (O) -, cyclohexyl-C (O) -, (CH3) 2-CH-CH2-C (O) -, cyclopropyl-C (O) -, CH3-O-CH2-C (O) -, 2-chlorophenyl-C (O) -, C2H5-OC (O) -CH2-C (O) -, (CH3) 2-CH- C (O) -, 2-tetrahydrofuryl-C (O) -, (CH3O) (CH3) CC (O) -, CF3-CH2-C (O) -, 15-cyclopropyl-CH2-C (O) -, CH3S-CH2-C (O) -, (CH3) 2 N-CH2-C (O) - or (CH3) 2C ( OH) - C (O) -; • X is 6-chloro, 6-fluoro, 6-cyano or 6-nitro; and n is 1. The individual preferred compounds of this invention are: 3-amino-2-benzoyl-6-chloroindole; 3-acetylamino-2-benzoyl-6-chloroindole; 2-benzoyl-6-chloro-3- (isobutyrylamino) indole; 3- (benzamido) -2-benzoyl-6-chloroindole; 2-benzoyl-6-chloro-3- (propionylamino) indole; 2-benzoyl-3- (butyrylamino) -6-chloroindole; 2-benzoyl-6-chloro-3- (cyclohexylcarboxamido) -indole; 2- benzoyl-6-chloro-3- (isovalerylamino) indole; 2-benzoyl-6-chloro-3- (cyclopropylcarboxamido) indole; 2-benzoyl-6-chloro-3- (methoxyacetylamino) indole; 3- amino-6-chloro-2- (3-methoxybenzoyl) indole; 3-acetylamino-6-chloro-2- (3-methoxybenzoyl) indole; 3-amino-6-chloro-2- (3-methylbenzoyl) indole; 3-acetylamino-6-chloro-2- (3-methylbenzoyl) indole; 6-chloro-2- (3-methylbenzoyl) -3- 5 (propionylamino) indole; 6-chloro-3- (methoxyacetylamino) -2- (3-methylbenzoyl) indole; 3- amino-6-chloro-2- (3-chlorobenzoyl) indole; 3-acetylamino-6-chloro-2- (3-chlorobenzoyl) indole; 6-chloro-2- (3-chlorobenzoyl) -3- (propionylamino) indole; 3- (butyrylamino) -6-chloro-2- (3-chlorobenzoyl) indole; 6-chloro-2- (3-chlorobenzoyl) -3- (isovalerylamino) indo; 6-chloro-2- (3-chlorobenzoyl) -3- (methoxyacetylamino) indole; 3-acetylamino-6- 10 chloro-2- (3-fluorobenzoyl) indole; 3-amino-2- (3-bromobenzoyl) -6-chloroindole; 3- acetylamino-2- (3-bromobenzoyl) -6-chloroindole; 2-benzoyl-6-chloro-3- (2-chlorobenzamido) indole; 2-benzoyl-6-chloro-3 - [(3-ethoxycarbonyl) propionylamino] indole; (s) - (+) -2-benzoyl-6-chloro-3 - [(2-hydroxypropionyl) amino] indole; 3-amino-6-chloro-2- (4-chloropyridine-2-carbonyl) indole, 3-acetylamino-6-chloro-2- (4- 15 chloropyridine-2-carbonyl) indole; 3-amino-6-chloro-2- (4-methylpyridine-2-carbonyl) indole; 3-acetylamino-6-chloro-2- (4-methylpyridine-2-carbonyl) indole; 3-amino-6-chloro-2- (4-methoxypyridine-2-carbonyl) indole; 3-acetylamino-6-chloro-2- (4-methoxypyridine-2-carbonyl) indole; 6-chloro-3-isovalerylamino-2- (4-methoxypyridine-2-carbonyl) indole; 3-acetylamino-6-chloro-2- (pyrzine-2-carbonyl) ddol; 3-acetylamino-6-chloro-2- (cyclohexanecarbonyl) indole; 3-acetylamino-2-benzoyl-6-fluoroindole; 3- acetylamino-2-benzoyl-6-cyanoindole; 2-benzoyl-6-chloro-3 - [(2-tetrahydrofuryl) carboxamido) indole; 2-benzoyl-6-chloro-3 - [(2-methoxypropionyl) amino] indole; 2- benzoyl-6-chloro-3- (3,3,3-trifluoropropionylamino) indole; 2-benzoyl-6-chloro-3- (cyclopropanoacetylamino) ddol; 2-benzoyl-6-chloro-3- (methylthioacetylamino) indole; 2-benzoyl-6-chloro-3 - [(N, N-dimethylaminoacetyl) amino] indole; 3-amino-6-chloro-2- (pyridine-2-carbonyl) indole; 3-acetylamino-6-chloro-2- (pyridine-2-carbonyl) indole; • 3-Acetylamino-2- (3-aminobenzoyl) -6-hydrochloride of 3-acetylamino-5- 2- (3-aminobenzoyl) -6-chloroindole; 3-Acetylamino-6-chloro-2- (3-methylcyclohexylcarboyl) ddol; 3- (N-acetyl-n-methylamino) -6-chloro-2- (3-chlorobenzoyl) indole 2-benzoyl-6-chloro-3- (N, N-dimethylamino) indole; 3-acetylamino-2-benzoyl-6-nitroindole; 3-acetylamino-6-chloro-2- (3-hydroxymethyl-2-furoyl) indole, 6-chloro-2- (4-chloropyridine-2-carbonyl) -3- (propionylamino) indole; 6-chloro-2- (4-chloropyridine-2- • 10-carbonyl) -3- (2-hydroxyisobutyrylamino) indole; 3-acetylamino-6-chloro-2- [2- (5-methylthiazolyl)] indole; 3- (2-Acetoxyisobutyrylamino) -6-chloro-2- (4-chloropyridine-2-carbonyl) indole; 6-chloro-2- (4-chloropyridine-2-carbonyl) -3- (isovalerylamino) indole; 6-chloro-2- (4-chloropyridine-2-carbonyl) -3 - [[(S) -2-hydroxypropionyl] amino] indole; 3- (N-Acetyl-N-methylamino) -6-chloro-2- (4-chloropyridine-2-carbonyl) indole; Y 2- (4-aminopyridine-2-carbonyl) -6-chloro-3- (propionylamino) indole hydrochloride. The most preferred individual compounds are: P 3-acetylamino-2-benzoyl-6-chloroindole; 2-benzoyl-6-chloro-3- (isovalerylamino) indole; 3-Acetylamino-6-chloro-2- (3-methylbenzoyl) indole; 3-Acetylamino-6-chloro-2- (3-chlorobenzoyl) ddol; 6-chloro-2- (3-chlorobenzoyl) -3- (propionylamino) indole; 3- 20-acetylamino-6-chloro-2- (4-chloropyridine-2-carbonyl) indole; 3-acetylamino-6-chloro-2- (4-methylpyridine-2-carbonyl) indole; 2-benzoyl-6-chloro-3- (methylthioacetylamino) indole; 6-chloro-2- (4-chloropyridine-2-carbonyl) -3- (propionlamino) indole; 3-acetylamino-6-chloro-2- (3-hydroxymethyl-2-furoyl) indole; and 6.chloro-2- (4-chloropyridine-2-carbonyl) -3- (2-hydroxyisobutyrylamino) indole; 3-Acetylamino-6-chloro-2- [2- (5-methylthiazole)] indole. The most preferred individual compounds are: 3-acetylamino-2-benzoyl-6-chloroindole; 2-benzoyl-6-chloro-3- (isovalerylamino) indole; 3-Acetylamino-6-chloro-2- (3-methylbenzoyl) idol; 3-Acetylamino-6-chloro-2- (3-chlorobenzoyl) indole; 6-chloro-2- (3-chlorobenzoyl) -3- (propionylamino) indole; 3- acetylamino-6-chloro-2- (4-methylpyridine-2-carbonyl) indole; 2-benzoyl-6-chloro-3- (methylthioacetylamino) indole; 6-chloro-2- (4-chloropyridine-2-carbonyl) -3- (propionylamino) indole; and 6-chloro-2- (4-chloropyridine-2-carbonyl) -3- (2- (hydroxyisobutyrylamino) indole. General Synthesis A compound of the general formula (I) can be prepared by any synthetic procedure applicable to the compounds related in structure known to those skilled in the art.

Representative examples, as described hereinafter, are illustrative of the invention in which, unless otherwise indicated, L, Q, X, Y, R1, R2 ,. R3, R4, R5, Z, m, n, p, q, and n are as defined above.

SCHEME 1 20 In one embodiment, a compound of the formula (III) is prepared according to the reaction steps indicated in scheme 1. The compounds of the formula (III) correspond to those of the formula (I) in which Jí¡ »1-; «* R2 is -C (O) -R5 PROCEDURE A? (II) (I ") O A s (2) R1-D 15 (3) Hydrolysis [R1 is not H] • PROCEDURE B SCHEME 1 In the formula (II), B is hydrogen or a suitable protecting group, for example, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl (Boc), - - * _ ^ - $ - ^ and ^^^^ - '^ benzyloxycarbonyl, phenylsulfonyl, p-toluenesulfonyl or the like. For example, in step 1 of Process A or Process B, a compound of formula (II) is reacted with a compound of formula A1-C (O) -OC (O) -A2 or R5C (O) -A , wherein A1 and A2 are, independently, C C4 alkyl or A1 and A2 together form C? _4 alkylene or C2_ al alkenylene, and A is defined such that the compound of R 5 C (O) -A is, for example , a carboxylic acid halide (e.g., chloride and bromouro), acyl halide, carboxylic acid, carboxylic acid ester (e.g., R5C (O) -O-C C alkyl and R5C (O) -O-aryl) [An example of the aryl is phenyl, naphtyl, furyl * 10 and thienyl], a carboxylic acid anhydride or the like In the present example, when a compound of the formula R5C (O) -A is, for example, a »Carboxylic acid halide (for example, chloride or bromide) or a carboxylic acid anhydride, the reactants can be heated in the absence or in the presence of a solvent inert to the reaction. Preferred reaction inert solvents include, but are not limited to, benzene, toluene, xylene, o-dichlorobenzene, nitrobenzene, 1,2-dichloroethane or the like. Preferably, the reaction is carried out in the presence of a base. A preferred base is selected from, for example, but without limitation, an alkali metal hydroxide, alkoxide, carbonate or hydride or Alkaline earth, such as sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium carbonate, potassium carbonate, sodium hydride or potassium hydride, or an amine such as triethylamine, tributylamine, diisopropylethylamine, pyridine or dimethylaminopyridine, in presence or absence of a solvent inert to the reaction. Preferred reaction inert solvents include, but are not limited to, benzene, toluene, xylene, o-dichlorobenzene, nitrobenzene, pyridine, dichloromethane, 1,2-dichloroethane, tetrahydrofuran or mixtures thereof. The reaction temperatures are generally in the range of -100 to 250 ° C, preferably in the range of 0 to 150 ° C, but, if necessary, lower or higher temperatures may be employed. The reaction times are, in general, from several minutes to a day, preferably from 20 minutes to 5 hours, however, if necessary, shorter or longer reaction times may be employed. Alternatively, when a compound of formula R5C (O) -A is, for example, a carboxylic acid, the intermediate amide obtained in step 1 in Process A or in Procedure B can be easily prepared by treatment of the required carboxylic acid with a compound of formula (II) in the presence of a coupling reagent such as, but not limited to, 1- (dimethylaminopropyl) -3-ethylcarbodiimide (WSC), N, N'-dicyclohexylcarbodiimidazole (DCC), carbonyldiimidazole, diethyl ester of cyanophosphonic acid or the like. Preferred reaction inert solvents include, but are not limited to, acetone, acetonitrile, dichloromethane, 1,2-dichloroethane, N.N-dimethylformamide, N, N-dimethylacetamide, dimethisulfoxide, dioxane, tetrahydrofuran or pyridine. Or, for example, under reaction conditions of the Mitsunobu type. A suitable condensation reagent in the Mitsunobu reaction is di-alkyl azodicarboxylate (C1.4) in the presence of a triarylphosphine, for example, diethyl azodicarboxylate in the presence of triphenylphosphine. Solvents inert to the reaction of choice include tetrahydrofuran, dichloromethane, dimethylformamide, benzene, toluene or the like. The reaction temperature is preferably in the range of 0 ° C to the reflux temperature of the solvent, for example, from 0 to 100 ° C, but, if necessary, lower or higher temperatures can be adopted. The reaction times are, in general, from several minutes to a day, preferably from 20 minutes to 5 hours, however, if necessary, shorter or longer reaction times may be employed. In stage 2 of Procedure B, the intermediate amide (the group B is a suitable protecting group as defined hereinabove) is reacted with a compound of formula R1-D, where D is selected from a suitable displaceable group, for example, a halo or sulphonyloxy group, eg, fluoro , chlorine, bromine, iodine, trifluoromethanesulfonyloxy, methanesulfonyloxy, benzenesulfonyloxy or p-toluenesulfonyloxy. Preferably, the present reaction is carried out in the presence of a suitable base, for example, an alkali metal or alkaline earth metal alkoxide, carbonate or hydride, such as, but not limited to, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium carbonate, potassium carbonate, sodium hydride or potassium hydride. Preferred reaction inert solvents include, but are not limited to, acetone, acetonitrile, N, N-dimethylformamide, N, N-dimethylacetamide, dimethisulfoxide, dioxane, tetrahydrofuran or pyridine. Preferably, the reaction temperatures f ^^^? f? ^ and? ^ -; they are in the range of -100 to 250 ° C, usually in the range of 0 ° C to the reflux temperature of the solvent, but, if necessary, lower or higher temperatures may be employed. The reaction time, in general, is • several minutes to one day, preferably, 30 minutes to 5 hours, however, if necessary, shorter or longer reaction times may be used. In step 2 of Process A or in step 3 of Process B (group B is a suitable protecting group as defined above in this document) group B can be removed by • Various conventional procedures known to those skilled in the art (for example, see "Protection of the Amino Group" in Protective Groups in Organic Synthesis, 2nd Edition, TW Greene and PGM Wuts, Ed., John Wiley and Sons, Inc. 1991, pp. 309-405).

SCHEME 2 • A compound of formula (III) can also be prepared according to the reaction indicated in Scheme 2.

SCHEME 2 In Scheme 2, X, Y, Q, R1, R5 and n are as defined above. The compound of formula (IV) (amide) is used only for illustrative purposes and is not intended to limit the scope of the present invention. Thus, for example, a compound of formula (IV) is treated with a compound of formula M-Y-Q in a solvent inert to the reaction. In a compound of formula M-Y-Q, M is defined so that a compound of formula M-Y-Q is, for example, the corresponding Grignard or alkali metal reagent, • For example, M can be magnesium chloride (QY-MgCI), magnesium bromide (QY-MgBr) or magnesium iodide (QY-Mgl), lithium (QY-Li), potassium (QYK) or sodium (QY- Na) Suitable alkali metal or Grignard reagents can be prepared easily, in situ, before use from the appropriate starting materials by conventional methods known per se. specialists in the art. Preferred reaction inert solvents include, but are not limited to, diethyl ether, tetrahydrofuran, dimethoxyethane, • dioxane, benzene, toluene, hexane, cyclohexane or mixtures thereof. The reaction temperatures are preferably in the range of -100 to 150 ° C, usually in the range of -70 ° C to the reflux temperature of the The solvent, preferably, of -40 ° C at room temperature, but if necessary, lower or higher temperatures may be employed. The reaction time in general is from several minutes to a day, preferably from 30 minutes to 5 hours, however, if necessary, shorter or longer reaction times may be employed. The compound of formula (IV) can be easily obtained by conventional synthetic methods known to those skilled in the art. • technique and, which, are suitably described within the accompanying non-limiting examples.

SCHEME 3 In another embodiment, the compounds of formula (I), wherein X, • Y, Q and n are as defined above, B is a suitable protecting group as defined above and both R 1 and R 2 are C 1-4 alkyl, are prepared according to the reaction steps indicated in Scheme 3. fifteen For example, a compound of formula (II) is reacted with a suitable carbaldehyde (such as formaldehyde, acetaldehyde and propionaldehyde) in the presence of a suitable reducing agent such as, but not limited to, sodium cyanoborohydride, sodium triacetoxyborohydride, 9-borabicyclo [3.3.1] nonanyl triethylborohydride (9-BBN) and lithium or the like (P.

C. Unangst, D. T. Connor and S. Russell Stabler, J. Heterocyclic Chem., 24, 817 (1987); R.F. Borch and A. I. Hassid, J. Org. Chem., 37, 1673 (1972)). Preferred reaction inert solvents include, but are not limited to, acid • acetic, N, N-dimethylformamide, N, N-dimethylacetamide, dimethisulfoxide, dioxane or tetrahydrofuran. The reaction temperatures are preferably in the range of -40 to 200 ° C, usually in the range of 0 ° C to the reflux temperature of the solvent, but, if necessary, higher or lower temperatures may be employed. The reaction time is, in general, from several minutes to a day, preferably from 30 minutes to 5 hours, • 10 however, if necessary, shorter or longer reaction times may be employed.

SCHEME 4 A compound of formula (II) can be prepared by various synthetic methods known to those skilled in the art. The following representative examples as described hereinafter, are illustrative and are not intended to limit the scope of the invention in any way.

(V) (ll) For example, a compound of formula (II), wherein B, X, Y, Q and n are as defined above, can be easily obtained from the appropriate 2-aminobenzonitrile (V) as it is illustrated in Scheme 4 (for example, see EE García, LE Benjamín and R. lan Fryer, J. 5 Hetererocycl, Chem., 10, 51 (1973)). Thus, the required 2-aminobenzonitrile (V) is reacted with a compound of formula (VI), wherein Y and Q are as defined above and E is halogen, preferably, iodine, bromine or chlorine, presence of an adequate base. A suitable base is, for example, an alkali metal alkoxide, carbonate or hydride W 10 or alkaline earth, such as, but not limited to, sodium tert-butoxide, potassium tert-butoxide, sodium carbonate, potassium carbonate, sodium hydride or potassium hydride. Preferred reaction inert solvents include, but are not limited to acetonitrile, N, N-dimethylformamide, N, N-dimethylacetamide, dimethisulfoxide, dioxane or tetrahydrofuran. Reaction temperatures are preferably in the range of -40 to 250 ° C, usually in the range of 0 ° C to the reflux temperature of the solvent, but, if necessary, lower or higher temperatures may be employed. The reaction time, in general, is from several minutes to a day, preferably from 30 minutes to 5 hours, however, if necessary, times may be used. reaction times shorter or longer.

SCHEME S Alternatively, a compound of formula (II), wherein X, Y, Q and n are as defined above and B is hydrogen, can be prepared according to the reaction steps depicted in Scheme 5.

• (IX) SCHEME S 20 For example, the compound of formula (II) can be prepared from the required nitro compound of formula (VIII), by reduction in the presence of a suitable reducing agent by procedures ß ^ f .. _ - _-? ¿_-í .. conventional ones known to those skilled in the art. For example, tin (II) chloride in ethanol (FD Bellamy and K. Ou, Tetrahedron Lett., 25, 839 (1984)), iron chloride ammonium in aqueous ethanol (K. Ramadas and N. f Srinivasan, Synth. Commun., 22, 3189 (1992)) or zinc or iron powder in acetic acid (E. Werteim, Org Synth, Coll. Vol. 2., 160 (1943)), or by catalytic hydrogenolysis. Preferred catalysts are, for example, palladium on carbon or Raney Nickel (C. F. H. Alien and J. Vanallan, Org. Synth., Coll. Vol. 3., 63 (1955)). The nitro compound of formula (VIII) can be easily obtained by conventional synthetic procedures known to • 10 specialists in the art and, which, are suitably described within the attached non-limiting examples. The starting material of formulas II, IV, V, VI, VII and IX in the general syntheses mentioned above can be obtained by conventional methods known to those skilled in the art.

The preparation of such starting materials is described within the attached non-limiting examples which are provided for the purpose of illustration only. Alternatively, the necessary starting materials can be obtained by procedures analogous to those described below, or by modifications thereof. The products that are discussed in the general syntheses mentioned above and illustrated in the experimental examples described herein below, can be isolated by conventional methods and the purification can be achieved by conventional means known to those skilled in the art., such as distillation, crystallization or chromatographic techniques. The compounds of the present invention which contain one or more double bonds and / or asymmetric centers may exist in various stereoisomeric forms. All such individual forms and mixtures thereof are included within the scope of the invention. The various isomers can be obtained by conventional methods. For example, cis / trans mixtures can be separated into the individual stereoisomers by stereoselective synthesis or by separation of the mixtures by fractional or chromatrographic crystallization techniques. Various compounds of the present invention can form addition salts with inorganic and organic acids. The salts of pharmaceutically acceptable acids of the compounds of the present invention are those which form non-toxic addition salts, such as, but not limited to, hydrochloride, hydrobromide, hydroiodide, nitrate, sulfate or acetate, fumarate, tartrate, succinate, maleate, gluconate, saccharate, benzoate, methanesulfonate, benzenesulfonate, p-toluenesulfonate and pamoate (ie, 1, 1 '-methylene- »/' s- (2-hydroxy-3-naphthoate)). The compounds of the invention that also have groups Acids are capable of forming base salts with various pharmaceutically acceptable cations. Examples of such salts include the alkali metal or alkaline earth metal salts and, particularly, the sodium or potassium salts. All these salts are prepared by techniques SP51 conventional. For example, these salts can be easily prepared by treating the aforementioned compounds with an aqueous solution containing the desired pharmaceutically acceptable cation and then evaporating the resulting solution to dryness, preferably under reduced pressure. Alternatively, it can also be prepared by mixing together with a lower alkoxide and then evaporating the resulting solution to dryness in the same manner as indicated above. In any case, stoichiometric amounts of reagents are preferably employed to ensure that the reaction is complete and that maximum yields of the desired final product are obtained. Bioprecursors (also called pro-drugs) of the compounds of the formula (I) are also included within the scope of this invention. A bioprecursor of a compound of the formula (I) is a chemical derivative thereof which is easily converted to the parent compound of the formula (I) in biological systems. In particular, a biprecursor of a compound of the formula (I) is converted to the parent compound of the formula (I) after the bioprecursor has been administered and absorbed by a mammalian subject, for example, a human. When the compounds of the formula (I) of this invention can form solvates such as hydrates, such solvates are included within the scope of this invention. The compounds of the formula (I) of this invention can be administered to mammals orally, parenterally or topically. In general, these compounds are administered, most desirably, to humans in doses ranging from 0.01 mg to 100 mg per kg of body weight per day, although variations will necessarily occur depending on the • Weight, sex and condition of the subject to be treated, the state of the disease being treated and the particular route of administration chosen. However, for the treatment of the aforementioned diseases in humans, a dosage level that is in the range of 0.1 mg to 10 mg per kg of body weight per day, in a single dose, is most desirably used. dose or in divided doses. The compounds of the present invention can be administered alone or in combination with pharmaceutically acceptable carriers or diluents, by any of the routes indicated above, and such administration can be carried out in a single dose or in multiple doses. More particularly, the novel therapeutic agents of the invention can may be administered in a wide variety of different dosage forms, i.e. may be combined with various inert pharmaceutically acceptable carriers in the form of tablets, capsules, troches, hard candies, powders, sprays, creams, ointments, suppositories, jellies, gels pastes, lotions, ointments, water suspensions, injectable solutions, elixirs, syrups and the like. Such vehicles include solid diluents or fillers, sterile aqueous media, various non-toxic organic solvents, etc. In addition, oral pharmaceutical compositions can be conveniently sweetened and / or flavored. In general, the therapeutically effective compounds of this invention are present in such dosage forms at concentration levels ranging between 5% and 70% by weight, preferably between 10% and 50% by weight. For oral administration, tablets containing various such as microcrystalline cellulose, sodium citrate may be employed, calcium carbonate, dipotassium phosphate and glycine, together with various disintegrants such as starch and, preferably, corn starch, potato or tapioca, alginic acid and certain complex silicates, together with granulation binders such as polyvinylpyrrolidone, sucrose, gelatin and gum arabic . In addition, lubricating agents such as magnesium stearate, sodium lauryl sulfate and talc are often very useful for forming tablets. Solid compositions of a similar type can also be used as filling gelatin capsules; Preferred materials in this regard also include lactose or milk sugar, as well as high molecular weight polyethylene glycols. When aqueous suspensions and / or elixirs are desired for oral administration, the active ingredient may be combined with various sweetening or flavoring agents, coloring materials or dyes and, if desired, emulsifying and / or suspending agents, as well as, together with diluents such as water, ethanol, propylene glycol, glycerin and various combinations thereof. For parenteral administration, solutions of a compound of the present invention in sesame or peanut oil or in an aqueous propylene glycol can be employed. The aqueous solutions should be buffered conveniently (preferably at pH> 8) if necessary and the liquid diluent must first be made isotonic. These aqueous solutions are suitable for intravenous injection purposes. Oily solutions are suitable for intra-articular, intra-muscular and subcutaneous injection purposes. The preparation of all these solutions under sterile condns is easily accomplished by conventional pharmaceutical techniques well known to those skilled in the art. In addn, it is also possible to administer the compounds of the present invention topically when treating inflammatory condns of the skin, and this can be accomplished preferably by means of creams, jellies, gels, pastes, ointments and the like, in accordance with conventional pharmaceutical practice. The compounds of the present invention can also be used in partial or complete co-administration, with other conventional anti-inflammatories, such as, steroids, conventional NSAIDs, inhibitors of 5-lipo-oxygenase, LTD4 agonists, LTB antagonists and inhibitors of LTA4 hydrolase. Suitable conventional anti-inflammatories include, but are not limited to, for example, indomethacin, diclofenac, piroxicam, nimesulide, tenidap, ebselen, masoprocol, zileuton, pranlukast, zafiriukast, montelukast, tepoxalin, rilopirox, flezelastine hydrochloride, phosphate enazadrem and bunaprolast. faith ._3SK_á .: BIOLOGICAL EVALUATION The activity of the compounds of the formula (I) of the present invention is demonstrated by the following tests. Endothelial cells were acquired from the human umbilical vein (HUVEC), which were characterized by positive staining with Willibrand factor and by an acetylated low density lipoprotein uptake, from Morinaga Bioscience Lab., Yokohama, Japan. The HUVEC were maintained in E-GM UV (from Kurashikibouseki Co., Neyagawa, Japan) in 5% C02 / 95% air at 37 ° C. PGE2, TXB2 and 6-keto-PGF1a were from Cayman Chemical Co. (Ann Arbor, USA): Human recombinant interleukin-1β (hIL-1β) was from R &D Systems (Minneapolis, USA). The RIA equipment for PGE2, TXB and 6-keto-PGF1a came from Amersham (Tokyo, Japan). Nodomethacin and other reagents were from Sigma Chemical Co. (St. Louis, USA). Dexamethosone (decadron [trademark]) was from Banyu Pharmaceutical Co. (Tokyo, Japan). The Vacutainer [Trade Mark] came from Becton Dickinson (Bedford, USA). Male Sprague-Dawley rats were purchased from Charles River (Hino, Japan).

CQX-1 Assay Based on Human Cells Human peripheral blood obtained from healthy volunteers was diluted to 1/10 volume with 3.8% sodium citrate solution. The platelet-rich plasma obtained immediately was washed with 0.14 M sodium chloride containing 12 mM Tris-HCl (pH 7.4) and 1.2 mM EDTA. The platelets were then washed with platelet buffer (Hanks buffer (without Ca) containing 0.2% BSA and 20 mM Hepes). Finally, human platelets • Washes (HWP) were suspended in platelet buffer at a concentration of 2.85 x 10 7 cells / ml and stored at room temperature until use. The suspension of HWP (aliquots of 70 μl, final concentration 2.0 x 10 7 cells / ml) was placed in a 96-well U-bottom plate and aliquots of 10 μl of 12.6 mM CaCl 2 were added. The platelets were incubated with A23187 (final concentration 10 μM, Sigma), with the test compound (0.1-100 μM) • 10 dissolved in DMSO (final concentration, less than 0.01%) at 37 ° C, for 15 minutes. The reaction was stopped by the addition of EDTA (7.7 mM final concentration) and the TxB2 was quantified in the supernatant using radioimmunoassay equipment (Amersham) according to the manufacturer's procedure. 15 COX-2 assay basing on human cells • Inhibition of COX-2 activity after induction of COX-2 by hlL-1 ß 20 In COX-2 assay based on human cells was performed as previously described (Moore et al, 1996). Confluent human umbilical vein endothelial cells (HUVEC Morinaga) were washed in a 96-well U-shaped bottom plate with 100 μl of RPMl 1640 containing 2% FCS and incubated with IL-1β (concentration final, 300 U / ml R &D Systems) at 37 ° C for 24 hours. After washing, the activated HUVEC were stimulated with A23187 (final concentration 30 μM) in • Hanks buffer containing 0.2% BSA, 20 mM Hepes and test compound (0.1 mM - 100 μM) dissolved in DMSO (final concentration, less than 0.01%) at 37 ° C, for 15 minutes. The 6-keto-PGFIa, a stable metabolite of PG12, was quantified in the supernatant, after adequate dilution, by the use of radioimmunoassay equipment (Amersham) according to the manufacturer's procedure. • 10 Inhibition of COX-2 during the induction phase Confluent human umbilical vein endothelial cells (HUVEC Morinaga) were washed in a 96-well U-shaped bottom plate with 100 μl of RPMl 1640 containing FCS at room temperature. 2% and composed of assay (0.1 nM- 100 μM) dissolved in DMSO (final concentration, less than 0.01%) and incubated with hIL-1β (final concentration, 300 U / ml R & D • Systems) at 37 ° C for 24 hours. After washing, the activated HUVEC were stimulated with A23187 (final concentration 30 μM) in Hanks buffer containing 0.2% BSA and 20 mM Hepes at 37 ° C, for 15 minutes. HE quantified 6-keto-PGF1a, a stable metabolite of PGI2, in the supernatant, after adequate dilution, by using a radioimmunoassay equipment (Amersham) according to the manufacturer's procedure.

Paw edema induced by carrageenan in rats < Male Sprague-Dawley rats (5 weeks old, Charles River Japan) were fasted overnight. Using a marker, it • drew a line above the ankle of the right hind leg and measured the volume of the leg (VO) by water displacement using a plethysmometer (Muromachi). The animals received orally vehicle (0.1% hypromellose or 5% Tween 80) or a test compound (2.5 ml per 100 g of body weight). One hour later, the animals were injected intradermally -carrageenan (0.1 ml of a 1% w / v suspension in saline solution, Zushikagaku) in the right hind paw (Winter et al, 1962; Lombardino et al, 1975) and three hours later, the paw volume (V3) was measured and the increase in volume was calculated (V3-V0 ). Since the maximum inhibition that can be obtained with classical NSAIDs is 60-70%, the DE30 values were calculated. 15 Gastric ulceration in rats Gastric ulcerogenicity of the test compound was evaluated by a modification of the conventional procedure (Ezer et al, 1976, Cashin et al, 1977). Spregue male Dawley rats (5 weeks old, Charles River Japan) that had been fasted for one night, received orally (0.1% hypromellose or 5% Tween 80) or a test compound (1 ml per 100 g of body weight). Six hours later, the animals were sacrificed by cervical dislocation. The stomachs were removed and inflated with a 1% formalin solution (10 ml). The stomachs were cut open along the greater curvature. From the number of rats that showed at least one gastric ulcer or erosion ^ hemorrhagic (including echirnosis), the incidence of ulceration was calculated. The animals did not have access to food or water during the experiment.

Data analysis Statistical program packages, SYSTAT 10 (SYSTAT, INC.) And StatView (Abacus Cencepts, Inc.) for Macintosh were used. The differences between the group treated with test compounds and the control group were tested using A | MOVA. The Cl50 (DE30) values were calculated from the equation for the logarithmic linear regression line of concentration (dose) versus the percentage of inhibition. Most of the compounds prepared in the working examples, as described in this document below, were tested by these procedures, and showed Cl u values of 0.0001 μM to 15 μM with respect to the inhibition of COX-2. The selectivity of COX-2 can be determined by the ratio, in terms of the Cl50 value, db the inhibition of COX-1 with respect to the inhibition of COX-2. In general, it can be said that a compound showing a COX-2 / COX-1 inhibition ratio of more than 2 has a good selectivity for COX-2.

Some compounds prepared in the examples showed COX-2 / COX-1 inhibition ratios greater than 10. The following examples contain detailed descriptions of the • processes for the preparation of the compounds of formula (I). These detailed descriptions are within the scope and serve to exemplify the general synthesis procedures described above that are part of the invention. These detailed descriptions are presented for illustrative purposes only and should not be considered a restriction on the scope of the invention. • 10 EXAMPLES The invention is illustrated in the following non-limiting examples, in which, unless otherwise indicated: all operations are performed at room temperature, that is, in the range of 18-25 ° C; the evaporation of the solvent was carried out using a rotary evaporator under reduced pressure with a bath up to 60 ° C; the reactions were monitored by thin layer chromatography (tic) and the reaction times are only given for illustrative purposes; the melting points (p.f) given are without correct (the polymorphism can produce different fusion points); the structure and purity of all the isolated compounds was ensured by at least one of the following techniques: tic (plates pre-coated F-254 with silica gel 60 of Merck), mass spectrometry, nuclear magnetic resonance - * "ss * ter- _" »- (Rl ff) or microanalysis. The returns are provided for illustrative purposes only. Merck chromatography silica 60), mass spectrometry, nuclear magnetic resonance (NMR) or microanalysis. The returns are provided for illustrative purposes only. Flash column chromatography was performed using Merck silica gel 60 (ASTM, 230-400 mesh). Optical rotations were measured using a JASCO DIP-370 digital polarimeter (Japan Spectroscopic Co. Ltd). The NMR data were determined at 270 MHz (JEOL GX 270 spectrometer) using chloroform (99.8% D) or dimethylsulfoxide (99.9% D) deuterated as solvent, unless otherwise indicated, with respect to tetramethylsilane (TMS) as the standard internal in parts per million (ppm); the conventional abbreviations used were s = singlet, de = doublet, t = triplet, q = quadruplet, m = multiplet, a = width, Ex. = EXAMPLE, etc.

EXAMPLE 3-Amino-2-benzoyl-6-chloroindole Stage 1. 4-chloro-2- (ethoxycarbonyl) benzonitrile Procedure A: To a solution of 2-amino-4-chlorobenzonitrile (10.0 g 65.5 mmol) in DMF (30 ml) cooled to 0 ° C, sodium hydride (60% dispersion w / w in mineral oil, 2.75 g) was added. , 68.7 mmoles) in portions, over 10 hours. The mixture was stirred for 1 h at 0 ° C and then ethyl chloroformate (6.6 ml, 68J mmoles) was slowly added. After stirring for an additional hour at this temperature, the mixture was poured into water (300 ml) and extracted with diethyl ether (250 ml x 2). The combined organic extracts were washed consecutively with water (500 ml) and brine (500 ml) and then dried (MgSO4). Removal of the solvent gave 15.85 g (quant.) Of the title compound as yellow solids. As an alternative, Method B: To a suspension of 2-amino-4-chlorobenzonitrile (50 g, 0.33 mol) in a mixture of pyridine (40 ml, 0.50 mol) and dichloromethane (500 ml) cooled to 0 ° C, chloroformate was carefully added ethyl (35 ml, 0.37 moles). The mixture was allowed to warm to room temperature and stirred overnight. The mixture was poured into 2N aqueous HCl (300 ml) and extracted with dichloromethane (300 ml x 2). Removal of the solvent gave 75 g of crude product as a pale yellow solid. The solid was washed with a minimum amount of hexane to yield 64 g (86%) of the title compound as white solids. 1 H-NMR (CDCl 3) d: 8.35 (1 H, d, J = 1.8 Hz), 7.47 (H, d, J = 8.4 Hz), 7.17 (1 H, s a), 7.09 (1 H, dd, J = 8.4, 1.8 Hz), 4.28 (2H, q, J = 7.0 Hz), 1.35 (3H, t J = 7.0 Hz).

Step 2: 3-Amino-2-benzoyl-6 ^ oyoro-1- (ethoxycarboniQindol To a solution of 4-chloro-2- (ethoxycarbonyllamine) -benzonitrile (10.8 g) in DMF (50 ml) cooled to 0 ° C, sodium hydride (60% w / w dispersion in mineral oil, 2.0 g, 50 mmol) was added.The mixture was stirred for 5 30 minutes at 0 ° C and then 2-bromoacetophenone (9.9 g) was carefully added. 50 mmoles) After stirring for a further 15 h at 0 ° C, the mixture was poured into water (500 ml) and extracted with diethyl ether (500 ml x 2), after drying (MgSO 4) and after drying. Remove the solvent, the crude product was purified by flash chromatography eluting with ethyl acetate / hexane (1: 5) to • produce 11.8 g (72%) of the title compound as a brown amorphous solid. 1 H-NMR (CDCl 3) d: 8.26 (1 H, d, J = 1.8 Hz), 7.78-7.70 (2 H, m) 7.54 (1 H, d, J = 8.4 Hz), 7.50-7.39 (3H, m) , 7.31 (1 H, dd, J = 1.8, 8.4 Hz), 5J8 (2H, sa), 3.73 (2H, q J = 7.0 Hz), 0.84 (3H, t, J = 7.0 Hz). Step 3: 3-Amino-2-benzoyl-6-chloroindole The product of step 2 (4.5 g, 13 mmol) and K2CO3 (18 g, 130 mmol) were heated at reflux for 5 h in 50% aqueous ethanol. . The mixture was cooled and concentrated and the residue was partitioned between water (50 ml) and dichloromethane (100 ml). The organic extract was dried (MgSO 4) and the solvent was removed. The residual solid was recrystallized from hexane / ethyl acetate to yield 3.2 g (91%) of the title compound. P.f .: 128-130 ° C. 1 H-NMR (CDCl 3) 6: 7.85-7.76 (2H, m), 7.64 (1 H, s a), 7.59-7.49 (4H, m), 7.22 (1 H, d, J = ilfti * '? * - ^: 1.8? ®, 7.02 (1 H, dd, J = 1.8, 8% Hz), 5.60 (2H, s a). h EXAMPLE 2: 3-Acetylamino-2-benzoyl-6-chloroindole Procedure A: Step 1. 3-Acetylamino-2-benzoyl-6-chloro-1- (ethoxycarbonyl) indole To a solution of 3-amino-2-benzoyl-6-chloro-1- (ethoxycarbonyl) indole (300 mg, 0.88 mmoles, example 1, step 2) in a mixture of dichloromethane (10 ml) and pyridine (0.88 ml, 0.96 mmole), acetyl chloride (0.07 ml, 0.96 mmole) was added. After stirring for 4 h, the mixture was partitioned between 10% aqueous citric acid (50 ml) and diethyl ether (100 ml). The organic extract was washed consecutively with water (50 ml), saturated sodium bicarbonate (50 ml), water (50 ml) and brine (50 ml). After drying (MgSO 4) and removing the solvent, the crude product was purified by flash chromatography eluting with ethyl acetate / hexane (1: 1) to yield 183 mg (54%) of the title compound as a yellow oil. . 1 H-NMR (CDCl 3) d: 9.13 (1 H, s a), 8.15 (1 H, a), 7.90-7.70 (2H, m), 7. 65-7.40 (4H, m), 7.30-7.20 (1 H, m), 3.94 (2H, q, J = 7.0 Hz), 2.22 (3H, s), 0.96 (3H, t, J = 7.0 Hz).

Step 2. 3-Acetylamino-2-benzoyl-6-chloroindole To a solution of 3-acetylamino-2-benzoyl-6-chloro-1- (ethoxycarbonyl) indole (556 mg, 1.4 mmol) in ethanol. water (3: 1, 20 ml), • added KOH (85% granules, 480 mg, 7.2 mmol) and the mixture was heated to reflux temperature for 1 h. The mixture was cooled and concentrated and the residue was partitioned between water (50 ml) and diethyl ether (100 ml). The organic extract was washed with water (100 ml) and then with brine (100 ml). After drying (MgSO 4) and removing the solvent, the crude product was recrystallized from dichloromethane / hexane to yield 180 mg (41%) of the • 10 title compound in the form of a yellow powder. P.f .: 212-213 ° C. 1 H-NMR (CDCl 3) d: 9.90 (1 H, sa), 8.29-8.15 (2 H, m), 7.84-7.75 (2 H, m), 7.70-7.52 (3 H, m), 7.32-7.27 (1 H, m), 7.12 (1 H, dd, J = 1.83, 9.16 Hz), 2.26 (3H, s). IR (KBr) v: 3400, 1680, 1520, 1320 cm "1.

Procedure B: To a 0.2 M solution of pyridine in 1,2-dichloromethane (DCE, 62 μL, 12.5 μmol), a 0.1 M solution of 3-amine-2-benzoyl-6-chloroindole (Example 1) was added. in DCE (50 μl, 5.0 moles) and then a 0.1 M solution of acetyl chloride in DCE (90 μ \, 9.0 moles). The homogeneous mixture The resulting mixture was stirred for 4 h and then allowed to stand overnight. After adding ethyl acetate (90 // I), the resulting mixture was filtered through a column of aminopropylated silica gel (Bond Elut®, NH2, 100 mg / 1.0 ml), 5010-1140) which had been treated with ethyl acetate (150 μl) aitolófefeS use. The reaction vessel was washed with ethyl acetate (150 μ x 4) and each wash was filtered through the column of aminopropylated silica gel. The combined filtrate was concentrated in vacuo to give the • composed of the title in a quantitative yield (1.62 mg).

EXAMPLE. 3-EXAMPLE. 16 The compounds described below were prepared from 3-amino-2-benzoyl-6-chloro-1- (ethoxycarbonyl) indole (example 1, step 2) and the • Acid chloride or the acid anhydride required and available on the market, according to the procedure described in process A of example 2.

EXAMPLE 3 2-Benzoyl-6-chloro-3- (isobutyrylamino) indole 15 p.f .; 197-198 ° C (ethyl acetate / hexane) .1 H-NMR (CDCl 3) d: 10.16 (1 H, sa), 8.31 (1 H, d, J = 8.8 Hz), 8.23 (1 H, sa) , 7.83-7.72 (2H, m) 7.69-7.50 (3H, m), 7.27 (1 H, d, J = 1.8 Hz), 7.08 (1 H, dd, J = 1.8, 8.8 Hz), 2.78-2.60 ( 1H, m), 1.32 (6H, d, J = 7.0 Hz). 20 IR (KBr) v: 3300, 1670, 1620, 1580, 1520, 1320, 1230, 980, 740 cm "1 EXAMPLE 4: 3- (Benzamido) -2-benzoyl-6-chloroindole p.f .; 149-151 ° C (ethyl acetate / hexane). 1 H-NMR (CDCl 3) d: 11.25 (1 H, s), 8.52 (1 H, d, J = 8.8 Hz), 8.26 (1 H, s), 8.11-8.04 (2H, m) 7.87-7.79 (2H, m), 7.68-7.48 (6H, m), 7.31 (1 H, d, J = 1.8 Hz), 7.14 (1 H, dd, J = 1.8, 8.8 Hz). IR (KBr) v: 1660, 1600, 1580, 1540, 1460, 1345, 1250, 1050, 920, 705 cm "1 EXAMPLE 5 2-benzoyl-6-chloro-3- (propionylamino) indole p.f .; 175-177 ° C (ethyl acetate / hexane) .1 H-NMR (CDCl 3) d: 10.02 (1 H, sa), 8.31 (1 H, d, J = 8.8 Hz), 8.18 (1 H, sa) , 7.83-7.76 (2H, m) 7.70-7.52 (3H, m), 7.30 (1 H, d, J = 1.8 Hz), 7.11 (1 H, dd, J = 1.8, 8.8 Hz), 2.52 (2H, q, J = 7.3 Hz), 1.30 (3H, t, J = 7.3 Hz). IR (KBr) v: 1660, 1620, 1570, 1540, 1320, 1240, 720 cm "1 EXAMPLE 6 3- (Acryloylamino) -2-benzoyl-6-chloroindole p.f .; 135-140 ° C (ethyl acetate / hexane) .1 H-NMR (CDCl 3) d: 10.29 (1 H, m), 8.69 (1 H, s), 8.35-8.25 (1 H, m), 7.81- 7.73 (2H, m), 7.65-7.49 (3H, m), 7.25 (1 H, d, J = 1.8 Hz), 7.05 (1H, dd, J = 1.8, 8.8 Hz), 6.50-6.30 (2H, m ), 5.81 (1 H, dd, J = 1.8, 9.5 Hz). IR (KBr) v: 1660, 1620, 1570, 1540, 1320, 1240, 990, 720 cm "1 EXAMPLE 7 2-benzoyl-3- (butyrylamino) -6-chloroindole p.f .; 158-161 ° C (ethyl acetate / hexane) .1 H-NMR (CDCl 3) d: 10.00 (1H, sa), 8.40-8.20 (2H, m), 7.88-7.75 (2H, m), 7.69- 7.50 (3H, m) 7.28 (1 H, s), 7.08 (1 H, d, J = 8.8 Hz), 2.44 (2H, t, J = 7.3 Hz), 1.90-1.70 (2H, m), 1.03 ( 3H, t, J = 7.3 Hz). IR (KBr) v: 1660, 1620, 1580, 1450, 1320, 1240, 1060, 920 cm "1 EXAMPLE 8 2-Benzoyl-6-chloro-3- (cyclohexylcarboxamido.indol) p.f .; 171-174 ° C (ethyl acetate / hexane) .1 H-NMR (CDCl 3) d: 10.18 (1 H, br s), 8.32 (1 H, d, J = 8.8 Hz), 8.23 (1 H, sa) , 7.85-7.76 (2H, m) 7.69-7.52 (3H, m), 7.26 (1 H, s), 7.07 (1 H, dd, J = 1.8, 8.8 Hz), 2.52-1.20 (11 H, m) . IR (KBr) v: 1660, 1620, 1580, 1540, 1320, 1250, 1230 cm "1 • p.f .; 189-192 ° C (ethyl acetate / hexane). 1 H-NMR (CDCl 3) d: 10.49 (1 H, sa), 8.35 (1 H, d, J = 8.8 Hz), 8.21 (1 H, sa), 7.85-7.74 (2H, m) 7.68- 7.52 (3H, m), 7.27 (1H, d, J = 1.8 Hz), 7.08 (1H, dd, J = 1.8, 8.8 Hz), 1.40 (9H, s). IR (KBr) v: 1655, 1600, 1580, 1490, 1480, 1350, 1250, 1200, 1010, 920 cm "1 • 10 EXAMPLE 10 2-Benzoyl-6-chloro-3- (isovalerylamino) indole p.f .; 187-190 ° C (ethyl acetate / hexane) .1 H-NMR (CDCl 3) d: 10.01 (1 H, br), 8.28 (1 H, d, J = 8.8 Hz), 8.25 (1 H, sa) , 7.86-7.76 (2H, m) 7.70- 15 7.52 (3H, m), 7.28 (1 H, d, J = 1.8 Hz), 7.09 (1 H, dd, J = 1.8, 8.8 Hz), 2.40-2.20 (3H, m), 1.05 (6H, d, J = 6.6 Hz). • IR (KBr) v: 1660, 1620, 1570, 1540, 1320, 1250 cm "1 EXAMPLE 11 20 2-Benzoyl-6-chloro-3- (cyclopropylcarboxamido) indole p.f .; 206-208 ° C (ethyl acetate / hexane) .1 H-NMR (CDCl 3) d: 10.25 (1 H, br), 8.29 (1 H, br), 8.24 (1 H, d, J = 9.2 Hz) , 7.84-7.76 (2H, m) 7.68- 7.52 (3H, m), 7.25 (1 H, d, J = 1.8 Hz), 7.05 (1H, dd, J = 1.8, 9.2 Hz), 1.80-1.62 (1 H, m), 1.20-1.09 (2H, m) 1.00-0.88 (2H, m). IR (KBr) v: 1660, 1620, 1580, 1450, 1320, 1240, 920 cm "1 EXAMPLE 12 2-Benzoyl-6-chloro-3- (valerylamino) indole p.f .; 140-143 ° C (ethyl acetate / hexane). 1 H-NMR (CDCl 3) d: 10.00 (1H, sa), 8.40-8.20 (2H, m), 7.87-7.75 (2H, m), 7.68-7.50 (3H, m) 7.27 10 (1 H, d, J = 1.8 Hz), 7.07 (1 H, dd, J = 1.8, 8.8 Hz), 2.53-2.42 (2H, m), 1.83 -1.70 (2H, m ), 1.54-1.37 (2H, m), 0.98 (3H, t, J = 7.4 Hz). IR (KBr) v: 1670, 1620, 1570, 1450, 1320, 1230, 740 cm "1 EXAMPLE 13 15 2-Benzoyl-6-chloro-3-r.thiophen-2-yl) carboxamido-indole p.f .; 222-225 ° C (ethyl acetate / hexane) .1 H-NMR (CDCl 3) d: 11.29 (1 H, s), 8.61-8.46 (1 H, m), 8.22 (1 H, s), 7.98- 7.78 (3H, m) 7.76-7.50 (3H, m), 7.42-7.08 (4H, m). 20 IR (KBr) v: 1640, 1580, 1540, 1465, 1250, 720 cm "1 ri * ^ - ^ EXAMPLE 14 2-Benzoyl-6-chloro-3- (3rfe (oropionylamino) indole • p.f .; 185-186 ° C (ethyl acetate / hexane) .1 H-NMR (CDCl 3) d: 9.89 (1 H, d), 8.26 (1 H, sa), 8.20 (1 H, d, J = 8.8 Hz) , 7.82-7.73 (2H, m) 7.68-7.51 (3H, m), 7.34-7.16 (6H, m), 7.09 (1 H, dd, J = 1.8, 8.8 Hz), 3.09 (2H, t, J = 7.3 Hz), 2.77 (2H, t, J = 7.3 Hz). IR (KBr) v: 1660, 1630, 1580, 1450, 1320, 1240, cm "1 EXAMPLE 15 2-Benzoyl-6-chloro-3- (trifluoroacetylamino) indole p.f .; 165-168 ° C (ethyl acetate / hexane) .1 H-NMR (CDCl 3) d: 11.17 (1 H, br), 8.47 (1 H, br), 8.32 (1 H, d, J = 8.8 Hz) , 7.88-7.79 (2H, m) 7.73- 15 7.56 (3H, m), 7.36 (1 H, d, J = 1.8 Hz), 7.18 (1 H, dd, J = 1.8, 8.8 Hz). IR (KBr) v: 1630, 1560, 1450, 1320, 1250, 1230 cm "1 EXAMPLE 16 2-Benzoyl-6-chloro- (methoxyacetylamino) indole 20 p.f .; 65-70 ° C. 1 H-NMR (CDCl 3) d: 10.42 (1 H, sa), 8.55 (1 H, sa), 8.23 (1 H, d, J = 8.8 Hz), 7.86-7.78 (2H, m) 7.68-7.50 (3H , m), 7.31 (1 H, d, J = 1.8 Hz), 7.11 (1H, dd, J = 1.8, 8.8 Hz), 4.08 (2H, s), 3.54 (3H, s).

IR ^ Br) v: 1680, 1660, 1580, 1540, 1340, 1320, 1250, 1110, 1020, 920 cm "EXAMPLE 17: 3-Acetylamino-6-chloro-2- (4-methoxybenzoyl) indole Step 1: 3-Amino-6-chloro-1-ethoxycarbonyl-2- (4-methoxybenzoic acid) The title compound was prepared according to the procedure described in step 2 of Example 1, starting from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2-bromo-4'- • 10-methoxyacetophenone 1H-NMR (CDCL3) d 8.23 (1 H, d, J = 1.5 Hz ), 7.73 (2H, d, J = 9.2 Hz), 7.54 (1 H, d J = 8.4 Hz), 7.25 (1 H, dd, J = 1.8, 8.4 Hz), 6.92 (2H, d, J = 9.2 Hz), 5.79 (2H, s), 3.84 (3H, s), 3.82 (2H, q, J = 7.0 Hz), 0.88 (3H, t, J = 7.0 Hz).

Step 2. 3-Acetylamino-6-chloro-1-ethoxycarboni-2- (4-methoxybenzoyl) indole • The title compound was prepared from 3-amino-6-chloro-1-ethoxycarbonyl-2- (4 -methoxybenzoyl) indole (step 1) according to the procedure described in step 1 of example 2 (Method A). 1 H-NMR (CDCl 3) d: 8.96 (1 H, sa), 8.13 (1 H, s), 7.80-7.71 (3H, m), 7.24 (1 H, dd, J = 1.8, 8.4 Hz), 6.93 (2H, d, J = 8.8 Hz), 4.04 (2H, q, J = 7.0 Hz), 3.86 (3H, s), 2.20 (3H, s), 1.02 (3H, t, J = 7.0 Hz).

Step 3. 3-Acetylamino-6-c ro-2- (4-methoxybenzoyl) indole The title compound was prepared according to the procedure described in step 2 of example 2 (method A), from 3 -acetylamino-6-chloro-1-ethoxycarbonyl-2- (4-methoxybenzoyl) idol (step 2). mp: 137-139 ° C (ethanol / hexane). 1 H-NMR (CDCl 3) d: 9.84 (1 H, sa), 8.28 (1 H, sa), 8.18 (1 H, d J = 8.8 Hz), 7.82 (2 H, d = 8.8 Hz), 7.30 (1 H , d, J = 1.8 Hz), 7.11 (1 H, dd, J = 1.8, 8.8 Hz), 7.05 (2H, d, J = 8.8 Hz), 3.91 (3H, s), 2.25 (3H, s). IR (KBr) v: 3450, 1650, 1620, 1600, 1570, 1540, 1320, 1260, 1250, 1170, 1020, 770 cm "1.

EXAMPLE 18 3-Amino-6-chloro-2- (3-methoxybenzoyl, ndol Step 1. 3-Amino-6-chloro-1-ethoxycarbonyl-2- (3-methoxybenzoyl) indole The title compound was prepared according to the procedure described in step 2 of example 1, starting from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2-bromo-3'-methoxyacetophenone. 1 H-NMR (CDCl 3) d: 8.25 (1 H, d, J = 1.5 Hz), 7.53 (1 H, d, J = 8.4 Hz), 7.36-7.26 (4 H, m), 7.05-7.01 (1 H, m), 5.78 (2H, s), 3.84 (3H, s), 3.78 (2H, q, J = 7.0 Hz), 0.89 (3H, t, J = 7.0 Hz).

Step 2. 3-Amino-6-chloro-2- (3-methoxybenzoyl) Tdol * ar A mixture of 3-amino-6-chloro-1-ethoxycarbonyl-2- (3-methoxybenzoyl) indole ( step 1, 998 mg, 2.68 mmol) and K2C03 (3J0 g, 26.8 mmol) in 70% aqueous ethanol (45 ml), was heated to reflux for 6.5 h then cooled to room temperature. The mixture was concentrated to approximately 20 ml, diluted with ethyl acetate (150 ml), the organic layer was washed with water (50 ml x 2) and dried (MgSO). After removing the solvent, the residue was purified by flash chromatography eluting with ethyl acetate / hexane (1: 4) to yield 549 mg (68%) of the title compound as a syrup. 1 H-NMR (CDCL 3) d: 7.62 (1 H, sa), 7.55-7.30 (5H, m), 7.23 (1 H, d, J = 1.5 Hz), 7.10 (1 H, ddd, J = 1.1, 2.6 and 8.1 Hz), 5.60 (2H, sa), 3.88 (3H, s).

EXAMPLE 19 3-Acetylamino-6-chloro-2- (3-methoxybenzoyl) indole To a solution of 3-amino-6-chloro-2- (3-methoxybenzoyl) indole (Example 18, 413 mg, 1.37 mmol) in dichloromethane (20 ml), pyridine (0.33 ml, 4.12 mmol) and acetyl chloride (0.14 ml, 2.06 mmol) were added. After stirring for 0.5 h, water (1 ml) and diethyl ether (100 ml) were added and the mixture was washed consecutively with 1N aqueous HCl (50 ml x 2) and saturated aqueous sodium bicarbonate (50 ml x 2). The organic layer was dried (MgSO4) and the solvent was removed. The resulting residue was purified by flash chromatography eluting with ethyl acetate / hexane (1: 2) to give the title compound as an oil. Crystallization of ethanol / hexane gave 260 mg (55%) of the title compound. P.f .: 161-162 ° C. 1 H-NMR (CDCl 3) d: 9.92 (1 H, sa), 8.32 (1 H, sa), 8.22 (1 H, d, J = 9.2 Hz), 7.47 (1 H, dd, J = 7.7 and 8.1 Hz ), 7.37-7.26 (3H, m), 7.18-7.08 (1 H, m), 7.10 (1 H, dd, J = 1.6 and 9.0 Hz), 3.88 (3H, s) and 2.25 (3H, s).

EXAMPLE 20 3-Acetylamino-6-chloro-2- (2-methylbenzoyl) indole • 10 Step 1. 3-Acetylamino-6-chloro-1-ethoxycarbonyl-2- (2-methylbenzoiDindol The title compound is prepared according to the procedure described in step 2 of example 1 and step 1 of example 2 (method A), from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2-bromo-2'-methylacetophenone (Baker et al., J. Chem.

• Soc, 1938, 445). 1 H-NMR (CDCl 3) d: 9.32 (1 H, sa), 8.14 (1 H, d, J = 1.8 Hz), 7.98 (1 H, d, J = 8.8 Hz), 7.42-7.10 (5H, m) , 3.93 (2H, q, J = 7.3 Hz), 2.58 (3H, s), 2.25 (3H, s), 1.03 (3H, t, J = 7.3 Hz). Step 2. 3-Acetylamino-6-chloro-2- (2-methylbenzoyl) idol The title compound was prepared according to the procedure described in step 2 of example 2 (Procedure A), starting from 3-Acetylamino-6-chloro-1-ethoxycarbonyl-2- (2-methylbenzoyl) indol. p.f .: 140- 142 ° C. 1 H-NMR (CDCL 3) d: 9.59 (1 H, sa), 8.29 (1 H, a), 8.21 (1 H, d, J = 8.8 Hz), 7.50-7.35 (4 H, m), 7.23 (1 H , d, J = 1.5 Hz), 7.07 (1 H, dd, J = 1.8, 8.8 Hz), 2.37 (3H, s), 2.19 (3H, s). IR (KBr) v: 1675, 1620, 1580, 1540, 1490 cm "1.

EXAMPLE 21 3-Amino-6-chloro- (3-methylbenzoyl) indole • Step 1. 3-Amino-6-chloro-2- (3-methylbenzoyl) -1- (ethoxycarbonyl) nol The title compound was prepared according to the procedure described in step 2 of the example 1, from 4-chloro-2- (ethoxycarbonylamino) benzonthiol (example 1, step 1) and 2-bromo-3'-methylacetophenoma (R. Yveline, G. Gerard and M. Geroges, Chem. Pharm. Bull., 1992, 40, 1170). Tick: Rf = 0.5 (25% ethyl acetate in hexanes).

• Step 2. 3-Amino-6-chloro-2- (3-methylbenzoyl) indole The title compound was prepared according to the procedure described in step 3 of example 1, starting from 3-amino-6-20. chloro-1-ethoxycarbonyl-2- (4-methylbenzoyl) idol (step 1). p.f .: 80-88 ° C. 1 H-NMR (CDCL3) d: 7.63 (1 H, sa), 7.60-7.38 (5H, m), 7.23 (1 H, d, J = 1.8 Hz), 7.02 (1 H, dd, J = 1.8, 8.8 Hz), 5.56 (2H, sa), 2.45 (3H, s).

EXAMPLE 22 3-Acetylamino-6-chloro-2- (3-methylbenzoyl) indole Step 1. 3-Acylamino-6-chloro-1-ethoxycarbonyl-2- (3-methylbenzoylDindole) The title compound was prepared according to the procedure described in step 1 of example 2 (method A), starting from 3-amino-6-chloro-2- (3-methylbenzoyl) -1- (ethoxycarbonyl) indole (example 21, step 1 ). 1 H-NMR (CDCL 3) d: 9.06 (1 H, sa), 8.20 (1 H, d, J = 1.5 Hz), 7.62-7.49 (2H, m), 7.40-7.24 (4H, m), 3.94 (2H , q, J = 7.0 Hz), 2.39 (3H, s), 2.22 (3H, s), 0.96 (3H, t, J = 7.0 Hz).

Step 2. 3-Acetylamlan-6-chloro-2- (3-methylbenzoyl) indole The title compound was prepared according to the procedure described in step 2 of example 2 (method A), starting from 3-Acetylamino-6-chloro-1-ethoxycarbonyl-2- (3-methylbenzoyl) indole (step 1). p.f .: 96-100 ° C. 1 H-NMR (CDCL 3) d: 9.86 (1 H, sa), 8.44 (1 H, sa), 8.18 (1 H, d, J = 9.2 Hz), 7.65-7.50 (2H, m), 7.50-7.35 ( 2H, m,), 7.27 (1 H d, J = 1.5 Hz), 7.07 (1 H, dd, J = 1.8, 8.8 Hz), 2.45 (3H, s), 2.22 (3H, s). IR (KBr) v: 1670, 1620, 1580, 1540, 1320 cm "1.

• The title compound was prepared according to the procedure described in example 19, using 3-amino-6-chloro-2- (3-methylbenzoyl) indole (example 21) and propionyl chloride. p.f .: 152-155 ° C. 1 H-NMR (CDCl 3) d: 10.02 (1 H, sa), 8.36-8.20 (2H, m), 7.63-7.51 (2H, m), 7.48-73.8 (2H, m), 7.28 (1H, d, J = 1.8 Hz), 7.08 (1 H, dd, J = 1.8, 9.2 Hz), 2.50 (2H, q, J = 7.7 Hz), 2.46 (3H, s), 1.29 (3H, t, J = 7.7 Hz ). • 10 EXAMPLE 24 3- (Butyrylamino) -6-Chloro-2- (3-methylbenzoyl.indol) The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (3-methylbenzoyl) indole (example 21) and butyryl chloride. p.f .: 127-130 ° C. 1 H-NMR (CDCl 3) d: 10.03 (1 H, sa), 8.35-8.20 (2 H, m), 7.62-7.54 (2 H, m), 7.48-7.40 (2 H, m), 7.28 (1 H, d, J = 1.8 Hz), 7.08 (1 H, dd, J = 1.8, 9.2 Hz), 2.55-2.35 (5H, m), 1.90-1.72 (2H, m), 1.04 (3H, t, J = 7.3 Hz) .

The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (3-methylbenzoyl) indole (example 21) and valeryl chloride. p.f .: 124-126 ° C. 1 H-NMR (CDCl 3) d: 10.02 (1 H, sa), 8.40-8.18 (2 H, m), 7.62-7.54 (2 H, m), 7.47-7.42 (2 H, m), 7.28 (1 H, s) , 7.09 (1 H, d, J = 8.8 Hz), 2.55-2.45 (5H, m), 1.82-1.68 (2H, m), 1.52-1.38 (2H, m), 0.98 (3H, t, J = 7.0 Hz).

EXAMPLE 26 6-Chloro-2- (3-methylbenzoiO-3- (isovalerylamino) indole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (3-methylbenzoyl) indole (example 21) and isovaleryl chloride. p.f .: 182-185 ° C. 1 H-NMR (CDCL 3) d: 10.05 (1 H, sa), 8.42-8.17 (2H, m), 7.62-7.53 (2H, m), 7.48-7.40 (2H, m), 7.30-7.25 (1H, m), 7.12-7.03 (1 H, m), 2.45 (3H, s), 2.39-2.17 (3H, m), 1.04 (6H, dd, J = 6.6 Hz).

EXAMPLE 27 6-Chloro-3- (methoxyacetylamino) -2- (3-methylbenzoyl) indole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-c! Gold-2- (3-methylbenzoyl) indol (Example 21) and methoxyacetyl chloride. p.f .: 155-157 ° C. 1 H-NMR (CDCl 3) d: 10.44 (1 H, sa), 8.47 (1 H, sa), 8.25 (1 H, d, J = 8.8 Hz), 7.63-7.53 (2 H, m), 7.49-7.38 ( 2H, m), 7.31 (1 H, d, J = 1.8 Hz), 7.10 (1 H, dd, J = 1.8, 8.8 Hz), 4.05 (2H, s), 3.52 (3H, s), 2.44 (3H , s).

EXAMPLE 28 3-Acetylamino-6-chloro-2- (4-methylbenzoyl) indole Step 1. 3-Acetylamino-6-chloro-1-ethoxycarbonyl-2- (4-methylbenzoicindinol) The title compound was prepared according to the procedure described in step 2 of example 1 and step 1 of example 2 ( procedure A), from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2-bromo-4'-methylacetophenone.1H-NMR (CDCL3) d: 8.98 (1H, s ), 8.23 (1 H, d, J = 1.8 Hz), 7.91 (1 H, d, J = 8.8 Hz), 7.67 (2 H, d, J = 8.1 Hz), 7.30 (1 H, dd, 1.8, 8.8 Hz), 7.26 (2H, d, J = 8.1 Hz), 3.93 (2H, q, J = 7.3 Hz), 2.42 (3H, s), 2.22 (3H, s), 0.96 (3H, t, J = 7.3 Hz).

Step 2. 3-Acetylamino-6-oloro-2- (4-methylbenzoyl) nol The title compound was prepared according to the procedure described in step 2 of example 2 (procedure A), starting from of 3-acetylamino-6-chloro-1-ethoxycarbonyl-2- (4-methylbenzoyl) indol (step 1). p.f .: 140-143 ° C. 1 H-NMR (CDCL 3) d: 9.91 (1 H, sa), 8.41 (1 H sa), 8.18 (1 H, d, J = 8.8 Hz), 7.71 (2 H, d, J = 8.1 Hz), 7.35 (2 H , d, J = 8.7 Hz), 7.27 (1 H, d, J = 2.2 Hz), 7.08 (1 H, dd, J = 1.8, 9.2 Hz), 2.46 (3 H, s), 2.23 (3 H, s) . IR (KBr) v: 1670, 1780, 1535, 1320 cm'1. • 10 EXAMPLE 29 3-Acetylamino-6-chloro-2- (2-chlorobenzoyl) indole Step 1, 3-Acetylamino-6-chloro-2- (2-chlorobenzoiD-1- (ethoxycarboniPindol) The title compound was prepared according to the procedure described in step 2 of example 1 and step 1 of the example 2 • (procedure A), starting from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, stage 1) and 2-bromo-2'-chloroacetophenone (A. Andreani, M. Rambaldi and A. Locatelli, Collect, Czech, Chem. Commun., 1991, 56, 2430-2435). 20 1 H-NMR (CDCL 3) d: 9.55 (1 H, sa), 8.17 (1 H, d, J = 1.5 Hz), 8.08 (1 H, d, J = 8.4 Hz), 7.52-7.27 (5H, m ), 4.00 (2H, q, J = 7.0 Hz), 2.27 (3H, s), 1.10 (3H, t, J = 7.0 Hz).

The phase compound was prepared according to the procedure described in Example 2, which was prepared in accordance with the procedure described in Example 3, 3-acetylamino-6-pho-2- (2-chlorobenzo-pindole). Stage 2 of Example 2 (procedure A), starting • of 3-acetylamino-6-chloro-2- (2-chlorobenzoyl) indole (step 1). 1 H-NMR (CDCl 3) d: 9.58 (1H, sa), 8.51 (1H, sa), 8.19 (1H, d, J = 8.8 Hz), 7.52-7.03 (6H, m), 2.18 (3H, s) .IR (KBr) v: 3300, 1680, 1620, 1580, 1540, 1340, 1320, 1240, 1060, 1020, 920, 760, 740 cm "1.

EXAMPLE 30 • 10 3-Amino-6-chloro-2- (3-chlorobenzoyl) indole Step 1. 3-Amino-6-chloro-2- (3-chlorobenzoyl) -1- (ethoxycarbonyl) d-ol The title compound was prepared according to the procedure described in step 2 of example 1, starting from 4 -chloro-2- 15 (ethoxycarbonylamine) benzonitrile (example 1, step 1) and 2-bromo-3'-chloroacetophenone (M.kihara, M. Hashimoto and Y. Kobayashi, Tetrahedron, 1992, f 48, 67- 78). 1 H-NMR (CDCL 3) d: 8.25 (1 H, d, J = 1.5 Hz), 7.74 (1 H, dd, J = 1.5, 2.2 Hz), 7.58 (1 H, dt, J = 1.5, 7.7 Hz) , 7.53 (1 H, d, J = 8.4 Hz), 7.47-7.43 (1 H, m), 7.37 (1 H, d, 20 J = 7.3 Hz), 7.32 (1 H, dd, J = 1.8, 8.4 Hz), 5.86 (2H, sa), 3.84 (2H, q, J = 7.0 Hz), 0.93 (3H, t, J = 7.0 Hz). s- «a: r **, t * Step 2. 3-amino-6-chloro-2- (3-chlorobenzoyl) indole The title compound was prepared according to the procedure described in step 3 of example 1, from 3-amino-6-chloro-2- (3-chlorobenzoyl) -1- (ethoxycarbonyl) indole (step 1). p.f .: 99-102 ° C. 1 H-NMR (CDCL 3) d: 7.78 (1 H, t, J = 1.5 Hz), 7.68 (1 H, ddd, J = 1.5, 1.8, 7.3 Hz), 7.55-7.44 (4H, m), 7.25 (1 H, d, J = 1.8 Hz), 7.04 (1 H, dd, J = 1.8, 8.8 Hz), 5.68 (2H, sa).

EXAMPLE 31 • 10 3-Acetylamino-6-chloro-2- (3-chlorobenzoyl) indole Step 1. 3-Acetylamine-6-chloro-2 (3-chlorobenzoit) -1- (ethoxycarbonyl) indole The title compound was prepared according to The procedure described in step 1 of example 2 (method A), starting from 3-amino-6-chloro-2- (3-chlorobenzoyl) -1- (ethoxycarbonyl) indol (example 30, step • 1) - 1H-NMR (CDCL3) d: 9.10 (1 H s a), 8.12-7.23 (7H, m), 4.05 (2H, q, J = 7.0 Hz9, 2. 23 (3H, s), 1.06 (3H, t, J = 7.0 Hz). Step 2. 3-Acetylamlan-6-chloro-2- (3-chlorobenzoyl) d-ol The title compound was prepared according to the procedure described in step 2 of example 2 (method A), from 3-acetylamino-6-chloro-2- (3-chlorobenzyl) (ethoxycarbonyl) idol (step 1), mp 152-154 ° C. (dichloromethane / hexane). CDCL3) d: 9.72 (1 H, sa), 8.90 (1 H, sa), 8.02 (1 H, d, J = 8.8 Hz), 7.73- • 7.00 (6H, m), 2.17 (3H, s). IR (KBr) v: ggjß, 1680, 1620, 1580, 1540, 1490, 1340, 1320, 1240, 1060, 1040, 920, 800, 730 cm "1.

EXAMPLE 32 6-Chloro-2- (3-chlorobenzoyl) -3- (propionylamino) indole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (3-chlorobenzoyl) indole (example 30) and propionyl chloride. mp: 129-130 ° C.1H-NMR (CDCL3) d: 9.95 (1 H, sa), 8.30 (1 H, d, J = 9.2 Hz), 8.17 (1 H, sa), 7.78- 7.59 (3H , m), 7.51 (1 H, t, J = 7.7 Hz), 7.32 (1 H, d, J = 1.1 Hz), 7.11 (1 H, dd, J = 1.8, 8.8 Hz), 4.48 (2H, q, J = 7.6 Hz), 1.30 (3H, t, J = 7.6 Hz).

EXAMPLE 33 3- (Butyrylamino) -6-chloro-2- (3-chlorobenzoyl) indole The title compound was prepared according to the procedure described in Example 19, using 3-amino-6-chloro-2- (3-chlorobenzoyl) indole (example 30) and butyryl chloride. mp: 157-158 ° C.1H-NMR (CDCL3) d: 9.96 (1 H, sa), 8.29 (1 H, d, J = 8.8 Hz), 8.17 (1 H, sa), 7.78 (1 H, dd, J = 1.5, 1.8 Hz), 7.70-7.59 Hz), 7.31 (1 H, d, J = 1.1 Hz), 7.11 (1 H, dd, J = 1.8, Hz), 1.88-1.75 (2H, m ), 1.05 (3H, t, J = 7.5 Hz). • EXAMPLE 34 6-Chloro-2- (3-chlorobenzoyl) -3- (valerylammon) indole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro- (3-chlorobenzoyl) indol (example 30) and valeryl chloride. mp: 159-160 ° C.1 H-NMR (CDCL3) d: 9.94 (1 H, sa), 8.28 (1 H, d, J = 9.2 Hz), 8.19 (1 H, sa), 7.77 (1 H , t, J = 1.8 Hz), 7.70-7.58 (2H, m), 7.51 (1 H, t, J = 7.7 Hz), 7.31 (1 H, d, J = 1.8 Hz), 7.11 (1 H, dd , J = 1.8, 8.8 Hz), 2.49 (2H, t, J = 7.3 Hz), 1.81-1.70 (2H, m), 1.51- 1.37 (2H, m), 0.97 (3H, t, J = 7.3 Hz) . EXAMPLE 35 6-Chloro-2- (3-chlorobenzoyl) -3- (isovalerylamino) indole The title compound was prepared in accordance with The procedure described in Example 19, employing 3-amino-6-chloro-2- (3-chlorobenzoyl) indole (example 30) and isovaleryl chloride. p.f .: 185-186 ° C. H- NMR (CDCL3) d: 9.94 (1 H, s a) 8.28 (1 H, d, J = 8.8 Hz), 8.19 (1 H, s a), 7.78 (1 H, t, J = 1.8 Hz), 7.68 (1 H, dt, J = 1.5, 1.5, 7.3 Hz), 7.61 (1 H, ddd, J = 1.5, 1.8, 8.1 Hz), 7.51 (1 H , t, J = 7.7 Hz), 7.31 (1 H, d, J = 1.5 Hz), 7.11 (1 H, dd, J = 1.8, 8.8 Hz), 2.37-2.20 (3H, m), 1.06 (6H, d, J = 6.2 Hz). f EXAMPLE 36 6-Chloro-2- (3-chlorobenzoyl) -3- (methoxyacetylamino) indole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (3-chlorobenzoyl) indole (example 30) and methoxyacetyl chloride. mp: 154-155 ° C.1H- f 10 NMR (CDCL3) d: 10.22 (1 H, sa), 8.41 (1 H, sa), 8.21 (1 H, d, J = 9.2 Hz), 7.77 (1 H, dd, J = 1.5, 2.2 Hz), 7.68 (1 H, ddd, J = 1.1, 1.5, 7.7 Hz), 7.59 (1 H, ddd, J = 1.1, 1.8, 7.7 Hz), 7.49 (1 H , dd, J = 7.7, 8.1 Hz), 7.34 (1 H, d, J = 1.8 Hz), 7.13 (1 H, dd, J = 1.8, 8.8 Hz), 4.05 (2H, s), 3.53 (3H, s).

EXAMPLE 37 3-Acetylamino-6-chloro-2- 4-chlorobenzoyl) indole • Step 1. 3-Acetylamino-6-chloro-1-ethoxycarbonyl-2- (4-chlorobenzoylindol) The title compound was prepared according to the procedure described in step 2 of example 1 and step 1 of example 2 ( procedure A), starting from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2-bromo-4'-chloroacetophenone. --sa_tt- ± _ - .... to 1 H-NMR (CDCL3) d: 9.06 (1 H, sa), 8.11 (1 H, sa), 7.82-7.69 (3H, m), 7.45-7.42 ( 2H, m), 7.27-7.24 (1H, m), 4.05 (2H, q, J = 7.0 Hz), 2.22 (3H, s), 1.07 (3H, t, J = 7.0 Hz).

Step 2. 3-Acetylamlan-6-chloro-2- (4-chlorobenzoyl) indole The title compound was prepared according to the procedure described in step 2 of example 2 (method A), starting from 3-Acetylamino-6-chloro-2- (4-chlorobenzoyl) -1- (ethoxycarbonyl) indole (step 1). p.f .: 175-176 ° C. (ethyl acetate / hexane). • 10 1 H-NMR (CDCL 3) d: 9.83 (1 H, sa), 8.22 (1 H, sa), 8.17 (1 H, sa), 7.77 (2 H, d, J = 8.4 Hz), 7.55 (2 H, d, J = 8.4 Hz), 7.30-7.26 (1 H, m), 7.13 (1 H, d, J = 8.8 Hz), 2.27 (3 H, s) .IR (KBr) v: 3450, 1660, 1620, 1590, 1540, 1320, 1250, 1090, 850, 760 cm "1.

EXAMPLE 38 3-Acetylamino-6-chloro-2- (3-fluorobenzoyl) indole • Step 1. 3-Acetylamino-6-chloro-1-ethoxycarbonyl-2- (3-fluorobenzoiPindol 20 The title compound was pre-prepared according to the procedure described in step 2 of example 1 and step 1 of example 2 (process A), starting from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2-bromo-3'-fluoroacetophenone (T. Rosen, AA Nagel, J. ^ * * ¡¡- «*" * * "^ ** a ^ íl * P. Rízzi, J. L. Ivés, J. B. Daffeh, et al., J. Med Chem., 1990, 33, 2715-2720). 1 H-NMR (CDCL 3) d: 9.05 (1 H, s a), 8.18 (1 H, d, J = 1.5 Hz), 7.88 (1 H, d, J = 8.4 Hz), 7.55-7.23 (5H, m), 4.01 (2H, q, J = 7.0 Hz), 2.24 (3H, s), 1.03 (3H, t, J = 7.0 • Hz). Step 2. 3-Acetylamino-6-chloro-2- (3-fluorobenzoyl) indole The title compound was prepared according to the procedure described in step 2 of example 2 (process A), starting from 3-acetylamino no-6-chloro-2- (3-fluorobenzoyl) -1- (ethoxycarbonyl) indole (step 1). p.f .: 201 -202 ° C. (ethanol). 10 1 H-NMR (CDCL 3) d: 9.89 (1 H, sa), 8.27-8.18 (2 H, m), 7.61-7.26 (5 H, m), 7.12 (1 H, dd, J = 1.8, 8.8 Hz), 2.27 (3H, s). IR (KBr) v: 3450, 1680, 1640, 1510, 1320, 1260, 1250, 860, 820, 520.cm "1.

EXAMPLE 39 15 3-Acetylamino-6-chloro-2- (4-chlorobenzoyl) indole Step 1. 3-Acetylamino-6-chloro-1-ethoxycarbonyl-2- (4-fluorobenzoiDindol The title compound was prepared in accordance with The procedure described in step 2 of example 1 and step 1 of example 2 (procedure A), from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2-bromo-4'-fluoroacetophenone. p.f.:196-198°C. 1H-NMR (CDCL3) d: 8.98 (1 H, sa), 8.17 (1 H, d, J = 1.5 Hz), 7.86-7.78 (3H, m), 7.28 (1 H, dd, J = 1.8, 8.8 Hz), 7.18-7.11 (2H, m), 4.02 (2H, q, J = 7.0 Hz), 2.23 (3H, s), 1.03 (3H, t, J = 7.0 Hz).

Step 2. 3-Acetylamino-6-chloro-2- (4-fluorobenzoyl!) Nol The title compound was prepared according to the procedure described in step 2 of example 2 (method A), starting from acetylamino-6-chloro-1-ethoxycarbonyl-2- (4-fluorobenzoyl) idol (step 1). p.f. : 205-207 ° C (ethanol / hexane) 1 H-NMR (CDCl 3) d: 9J 9 (1 H, s a), 8.24 (1 H, s a), 8.19 (1 H, d, J = • 10 9.2 Hz), 7.87-7.83 (2H, m), 7.30-7.22 (3H, m), 7.11 (1 H, dd, J = 1.8, 8.8 Hz), 2.25 (3H, s). IR (KBr) v: 3450, 1680, 1640, 1600, 1500, 1320, 1240, 840, 820, 600, 510 cm "1.

EXAMPLE 40 3-Amino-6-chloro-2- (4-methylthiobenzoyl) indole Step 3-Amino-6-chloro-1-ethoxycarbonyl-2- (4-methylthiobenzoiDindol) The title compound is prepared according to the procedure described in step 2 of example 1, from 4-chloro-2- (ethoxycarbonylamino) benzontril (example 1, step 1) and 2-bromo-4'-methylthioacetophenone (Cutler et al. , J. Am. Chem Soc, 1952, 74, 5475). 1H-d, 51 (3H, s), 0.89 (3H, t, J = 7.0 Hz).

Step 2. 3-Amino-6-chloro-l-p-methylthiobenzoyl) ndol The title compound was prepared according to the procedure described in step 3 of Example 1, starting from 3-amino-6-chloro- 1-Ethoxycarbonyl-2- (4-methyltiobenzoyl) indole (step 1). p.f .: 172-173 ° C. 1 H-NMR (CDCl 3) d: 7.11-712 (2H, m), 7.59 (1 H, sa), 7.53 (1 H, d, J = 8.8 Hz), 7.38-7.33 (2H, m), 7.23 (1 H, d, J = 1.5 Hz), 7.04 (1 H, dd, J = 1.8, 8.4 Hz), 5.57 (2H, sa), 2.55 (3H, s).

EXAMPLE 41 3-Acetylamino-6-chloro-2- (4-methylthiobenzyl) indole The title compound was prepared according to the procedure described in Example 19, starting from 3-amino-6-chloro-2- (4-methylthiobenzyl) indole (example 40). p.f .: 187-188 ° C. 1 H-NMR (CDCl 3) d: 9.87 (1 H, sa), 8.24 (1 H, sa), 8.20 (1 H, d, J = 8.4 Hz), 7.76-7.73 (2 H, m), 7.39-7.35 ( 2H, m), 7.29 (1 H, d, J = 1.5 Hz), 7.11 (1 H, dd, J = 1.8, 8.8 Hz), 2.56 (3H, s), 2.26 (3H, s).

EXAMPLE 42 3-Amino-2- (3-brom benzoyl) -6-chloroindole Step 1. 3-Amino-2- (3-bromobenzoyl) -6-chloro-1- (ethoxycarbonidindol) The title compound was prepared according to the procedure described in step 2 of example 1, starting with 4-chloro- 2- (Ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2-bromo-3'-bromoacetophenone 1 H-NMR (CDCl 3) d: 8.25 (1 H, d, J = 1.5 Hz), 7.90 (1 H, t, J = 1.8 Hz), 7.64-7.59 (2H, m), 7.54 (1H, d, J = 8.4 Hz), 7.34-7.26 (2H, m), 5.87 (2H, sa), 3.84 (2H , q, J = 7.0 Hz), 0.89 (3H, t, J = 7.0 Hz).

Step 2. 3-Amino-2- (3-bromobenzoyl) -6-chloro-inol The title compound was prepared according to the procedure described in step 3 of example 1, starting from 3-amino-2 - (3-bromobenzoyl) -6-chloro-1- (ethoxycarbonyl) indole (step 1). mp: 142-143 ° C 1 H-NMR (CDCl 3) d: 7.93 (1 H, dd, J = 1.5, 1.8 Hz), 7.74-7.66 (2 H, m), 7.53 (1 H, d J = 8.4 Hz) , 7.52 (1 H, sa), 7.41 (1 H, dd, J = 7.7, 8.1 Hz), 7.26 (1 H, d, J = 2.6 Hz), 7.04 (1 H, dd, J = 1.7, 8.4 Hz) 5.69 (2H, sa).

EXAMPLE 43 3-Acetylamino-2- (3-bromobenzoyl) -6-chloroindole • The title compound was prepared according to the procedure described in Example 19, starting from 3-amino-2- (3-bromobenzoyl) -6-chloroindole (example 42). 1 H-NMR (CDCl 3) d: 9.78 (1 H, sa), 8.22 (1 H, d, J = 8.8 Hz), 8.21 (1 H, sa), 7.93 (1 H, t, J = 1.8 Hz), 7.78 -7.70 (2H, m), 7.44 (1 H, t, J = 7.9 Hz), 7.32 (1 H, d, J = 1.5 Hz), 7.12 (1 H, dd, J = 1.8, 9.2 Hz) , 2.26 (3H, s). 10 EXAMPLE 44 3-Acetylamino-2- (3-benzyloxybenzoyl) -6-chloroindole Step 1. 3-Amino-2- (3-benzyloxybenzoyl) -6-chloro-1- 15 (ethoxycarboniPindol) The title compound was prepared according to • procedure described in step 2 of example 1, starting with 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2-bromo-3'- (benzyloxy) acetophenone (T. Fujií, M. Ohba, M. Tsuchida, K. Saito, Y. Hirano and J.

Sakaguchí, Chem. Pharm. Bull., 1986, 34, 496-507). 1 H-NMR (CDCl 3) d: 8.25 (1 H, d, J = 1.5 Hz), 7.60-7.23 (10 H, m), 7.18-7.06 (1 H, m), 5.76 (2 H, s), 5.11 (2 H , s), 3.74 (2H, q, J = 7.3 Hz), 0.85 (3H, t, J = 7.3 Hz).

Step 3-Acetylamine-2- (3-benzyloxybenzoyl) -6-chloro-1- (ethoxycarbonyl) indole The title compound was prepared according to the procedure described in step 1 of example 2 (procedure A), from 3-amino-2- (3-benzyloxybenzoyl) -6-chloro-1- (ethoxycarbonyl) indole (step 1) 1 H-NMR (CDCl 3) d: 9.02 (1 H, sa), 8.20 (1 H, s), 7.90 (1 H, J = 8.4 Hz), 7.48-7.16 (10H, m), 5.29 (2H, s), 3.91 (2H, q, J = 7.0 Hz), 2.22 (3H , s), 0.95 (3H, t, J = 7.0 Hz).

Step 3. 3-Acetylamino-2- (3-benzyloxybenzoyl) -6-chloro-inol The title compound was prepared according to the procedure described in step 2 of example 2 (procedure A), starting from of 3-acetylamino-2- (3-benzylloxybenzoyl) -6-chloro-1- (ethoxycarbonyl) indole (step 2). p.f .: 159-161 ° C. 1 H-NMR (CDCl 3) d: 9.88 (1 H, sa), 8.25 (1 H, sa), 8.21 (1 H, d, J = 9.2 Hz), 7.50-7.21 (10 H, m), 7.08 (1 H , dd, J = 8.8, 1.8 Hz), 5.14 (2H, s), 2.24 (3H, s).

EXAMPLE 45 3-Acetylamino-6-chloro-2- (3-hydroxybenzoyl) indole Hydrogenolysis was 3-acetylamine-2- (3-benzyloxybenzoyl) -6-chloroindole (example 44, 0.42 g, 1.0 mmol) in the presence of palladium on t - activated carbon (10%, ethyl (10 ml) and ethanol (1.0 ml) under pressure The mixture was filtered and the filtrate was concentrated in vacuo. • residual was recrystallized from ethyl acetate / hexane to yield 0.13 g (40%) of the title compound as a pale yellow solid, mp: 130-145 ° C. 1 H-NMR (CDCl 3) d: 11.73 (1 H, sa), 9.80-9.65 (2 H, m), 7.62 (1 H, d, J = 8.4 Hz), 7.50-6.98 (5 H, m), 1.76 (3 H , s). The signal due to OH H was not observed.

EXAMPLE 46 10 3-Acetylamino-6-chloro-2- (3,4-dichlorobenzoyl) indole Step L 3-Acetylamino-6-chloro-2- (3,4-dichlorobenzoyl) -1- (ethoxycarbonyl) indole The title compound was prepared according to the procedure described in step 2 of example 1 and the step 1 of example 2 (process A), starting from 4-chloro-2- (ethoxycarbonylamino) benzonitrile f (example 1, step 1) and 2-bromo-3'-4'-dichloroacetophenone. 1 H-NMR (CDCl 3) d: 9.11 (1 H, sa), 7.99 (1 H, d, J = 1.8 Hz), 7.92 (1 H, d, J = 1.8 Hz), 7.65 (1 H, d, J = 8.4 Hz), 7.57 (1 H, dd, J = 2.0, 8.2 Hz), 20 7.51 (1 H, d, J = 8.4 Hz), 7.20 (1 H, dd, J = 1.8, 8.8 Hz), 4.15 (2 H, q, J = 7.0 Hz), 2.21 (3H, s), 1.17 (3H, t, J = 7.0 Hz). f? ^^ h ^ ÉS¡¡ ^^ ii¡ ^ b¿ ^? ¿¿akiu ^^^ iMs¡? i? s.

Step 2: 3-Acetylamino-6-chloro-2-.3,4-dichlorobenzoyl) ddol The title compound was prepared according to the procedure described in step 2 of example 2 (procedure A), starting from of 3-acetylamino-6-chloro-2- (3,4-dichlorobenzoyl) -1- (ethoxycarbonyl) indole (step 1). p.f.:169-171 ° C. 1 H-NMR (CDCl 3) d: 9.74 (1 H, sa), 8.25 (1 H, sa), 8.19 (1 H, d, J = 9.2 Hz), 7.90 (1 H, t, J = 1.1 Hz), 7.64 (2H, sa), 7.31 (1 H, d, J = 1.5 Hz), 7.11 (1 H, dd, J = 1.8, 9.2 Hz), 2.26 (3H, s). IR (KBr) v: 3300, 1660, 1620, 1580, 1540, 1320, 1230, 1030, 800, 760 cm "1.

EXAMPLE 47 3-Amino-6-chloro-2- (3,5-difluorobenzoyl) indole Step 1. 3-Amino-6-chloro-2- (3,5-difluorobenzoyl) -1- (ethoxycarbonyl) indole The title compound was prepared according to the procedure described in step 3 of example 1, starting from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2-bromo-3 ', 5'-difluoroacetophenone (prepared according to the procedure of S. Kajigaeshi et al., Bull. Soc. Jpn., 1987 60, 1159-1160). 1 H-NMR (CDCl 3) d: 8.24 (1 H, d, J = 1.8 Hz), 7.54 (1 H, d, J = 8.4 Hz), 7.33 (1 H, dd, J = 1.8, 8.4 Hz), 7.29 -7.22 (2H, m), 6.97-6.88 (1H, m), 5.90 (2H, sa), 3.94 (2H, q, J = 7.0 Hz), 1.00 (3H, t, J = 7.0 Hz).

Step 2. 3-Amino-6-chloro-2- (3,5-difluorobenzoyl) indole The title compound was prepared according to the procedure described in step 2 of example 1, starting from 3-amino 6-chloro-2- (3,5-difluorobenzoyl) -1- (ethoxycarbonyl) indole (step 1). mp: 149-151 ° C 1 H-NMR (CDCl 3) d: 7.54 (1 H, d, J = 8.4 Hz), 7.45 (1 H, sa), 7.39-7.26 (3H, m), 7.06 (1 H, dd, J = 1.8, 8.4 Hz), 7.02-6.96 (1 H, m), 5.79 (2H, sa).

EXAMPLE 48 3-Acetylamino-6-chloro-2- (3,5-difluorobenzoyl) indole The title compound was prepared according to the procedure described in Example 19, starting from 3-amino-6-chloro-2- (3,5-difluorobenzoyl) indol (example 47). p.f .: 232-233 ° C. 1 H-NMR (CDCl 3) d: 9.87 (1 H, sa), 8.25 (1 H, d, J = 8.8 Hz), 8.18 (1 H, sa), 7.38-7.32 (3 H, m), 7.12 (1 H , dd, J = 1.8, 8.8 Hz), 7.09-7.04 (1 H, m), 2.28 (3H, s).

EXAMPLE 49 3-Amino-6-chloro-2- (3-trifluoromethylbenzoyl) nol Step 1, 3-Amino-6-chloro-1-ethoxycarbonyl-2- (3-trifluoromethylbenzoiDindol) The title compound was prepared according to the procedure described in step 2 of example 1, starting from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2-bromo-3'-trifluoromethylacetophenone (M. Kihara, M. Kashimoto and Y. Kobayashi, Tetrahedron, 1992, 48, 67-68). NMR (CDCl 3) d: 8.25 (1 H, d, J = 1.8 Hz), 8.03 (1 H, sa), 7.89 (1 H, da, J = 7.7 Hz), 7.74 (1 H, da, J = 8.1 Hz), 7.59-7.54 (2H, m), 7.33 (1 H, dd, J = 1.8, 8.4 Hz), 5.93 (2H, sa), 3.80 (2H, q, J = 7.0 Hz), 0.88 (3H, t, J = 7.0 Hz).

Step 2. 3-Amino-6-chloro-2- (3-trifluoromethylbenzoyl) indole The title compound was prepared according to the procedure described in step 3 of Example 1, starting with 3- amino- 6-chloro-1- (ethoxycarbonyl) -2- (3-trifluoromethylbenzoyl) indole (step 1). p.f .: 84-87 ° C. 1 H-NMR (CDCl 3) d: 8.07 (1 H, sa), 7.99 (1 H, da, J = 8.1 Hz), 7.82 (1 H, da, J = 7.7 H), 7.67 (1 H, t, J = 7.7 Hz), 7.55 (1 H, d, J = 8.8 Hz), 7.46 (1 H, sa), 7.26 (1 H, d, J = 2.2 Hz), 7.06 (1 H, dd, J = 1.8, 8.8 Hz), 5.72 (2H, sa). xrZfxVrizee? "" "« .S • The title compound was prepared in accordance with the The procedure described in Example 19, employing 3-amino-6-chloro-2- (3-trifluoromethylbenzoyl) indole (example 49) and isovaleryl chloride. p.f .: 179-180 ° C. 1 H-NMR (CDCl 3) d: 9.87 (1 H, s a), 8.27 (1 H, d, J = 8.8 Hz), 8.18 (1 H, s a), 8.07 (1H, s a), 8.00 (1 H, d, J = 8.1 Hz), 7.89 (1 H, d, J = 7.7 Hz), 7.71 (1 H, t, J = 7.7 Hz), 7.31 (1 H, d, J = 1.8 Hz), 7.13 (1 H, dd, J = 1.8, 8.8 Hz), • 10 2.37-2.20 (3H, m), 1.05 (6H, d, J = 6.2 Hz).

EXAMPLE 51 3-Amino-6-chloro-2- (4-trifluoromethoxybenzoyl) indole Step 3-Amino-6-chloro-ethoxycarbonyl-2- (4-trifluoromethoxybenzoiPindol) The title compound was prepared according to the procedure described in step 2 of Example 1, starting from 4-chloro-2- ( ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2-bromo-4'- 20 trifluoromethoxyacetophenone. 1 H-NMR (CDCl 3) d: 8.25 (1 H, d, J = 1.8 Hz), 7.82-7.77 (2H, m) , 7.54 (1 H, d, J = 8.4 Hz), 7.33-7.26 (3H, m), 5.88 (2H, s), 3.82 (2H, q, J = 7.2 Hz), 0.87 (3H, t, J = 7.2 Hz).

Step 2. 3-Amino-6-chloro-2- (4-fluoro-methoxy-benzoyl) -ol: The title compound was prepared according to the procedure described in step 3 of example 1, starting with 3-amino- 6- chloro-1- (ethoxycarbonyl) -2- (4-trifluoromethoxybenzoyl) idol (step 1). H-NMR (CDCl 3) d: 7.89-7.83 (2H, m), 7.54 (1 H, d, J = 8.8 Hz), 7.52 (1 H, sa), 7.37 (2H, da, J = 8.8 Hz), 7.24 (1 H, d, J = 1.5 Hz), 7.05 (1 H, dd, J = 1.6, 8.8 Hz, 5.70 (2H, sa). IR (KBr) v: 3350, 1620, 1610, 1490, 1260, 1210, 1170 cm "1. • 10 EXAMPLE 52 3-Acetylamino-6-chloro-2- (4-trifluoromethoxybenzoyl) indole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (4-15-trifluoromethoxy-benzoyl) indole (Example 51). mp: 213-214 ° C, 1 H-NMR (CDCl 3) d: 9.75 (1 H, sa), 8.23 (1 H, sa), 8.19 (1 H, d, J = 8.8 Hz), 7.89-7.85 (2H , m), 7.41 • (2H, d, J = 8.1 Hz), 7.31 (1 H, d, J = 1.8 Hz), 7.12 (1 H, dd, J = 1.8, 8.8 Hz), 2.25 (3H, s). IR (KBr) v: 3250, 1680, 1640, 1620, 1580, 1560, 1500, 1300, 1280, 1260, 1230, 1210, 1160, 920 cm "1.

EXAMPLE 53 3-Amino-6-chloro-2- (4-chloro-3-methylbenzoyl) indole Step 1. 3-Amino-6-chloro-2- (4-chloro-3-methylbenzoyl) -1- (ethoxycarbonyl) indole The title compound was prepared according to the procedure described in step 2 of example 1 , from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2-bromo-4'-chloro-3'-methylacetophenone. • 10 1-NMR (CDCl 3) d: 8.24 (1 H, d, J = 1.8 Hz), 7.63 (1 H, d, J = 2.2 Hz), 7.53 (1 H, d, J = 8.4 Hz), 7.50 -7.46 (1 H, m), 7.39 (1 H, d, J = 8.4 Hz), 7.31 (1 H, dd, J = 1.8, 8.4 Hz), 5.78 (2H, sa), 3.85 (2H, q, J = 7.0 Hz), 2.42 (3H, s), 0.92 (3H, t, J = 7.0 Hz).

Step 2. 3-Amino-6-chloro-2- (4-chloro-3-methylbenzoyl) indole The title compound was prepared according to the B procedure described in step 3 of example 1, starting from 3- amino-6-chloro-1- (ethoxycarbonyl) -2- (4-chloro-3-methylbenzoyl) indole (step 1). p.f .: 142-143 ° C. 20 1 H-NMR (CDCl 3) d: 7.68-7.40 (5H, m), 7.24 (1 H, d, J = 1.8 Hz), 7. 04 (1 H, dd, J = 1.5, 8.4 Hz), 5.60 (2H, s a), 2.47 (3H, s).

EXAMPLE 54 6-Chloro-2- (4-chloro-3-methylbe? Zoyl) -3- (sovalerylamino) -indole • The title compound was prepared according to the procedure described in example 19, using 3-amino-6-chloro-2- (4-chloro-3-methylbenzoyl) indole (example 53). p.f .: 202-203 ° C. 1 H-NMR (CDCl 3) d: 9.97 (1 H, sa), 8.27 (1 H, d, J = 9.2 Hz), 8.19 (1 H, sa), 7.71-7.51 (3H, m), 7.29 (1 H, d, J = 1.8 Hz), 7.10 (1 H, dd, J = 1.8, 9.2 Hz), 2.48 (3H, s), 2.36-2.23 (3H, m), 1.05 (6H, d, J = 6.2 Hz). • 10 EXAMPLE 55 2-Benzoyl-6-chloro-3- (2-chlorobenzamido) indole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-2-benzoyl-6-chloroindole (Example 1) and chlorobenzoyl chloride. p.f .: 229-234 ° C (dichloromethane / hexane). 1 H-NMR (DMSO-de) d: 11.98 (1 H, sa), 10.35 (1 H, s), 7.86-7.38 (9H, m), 7.34-7.24 (1 H, m), 7.18 (1 H, dd, J = 1.8, 8.8 Hz), 6.68 (1 H, d, J = 7.3 20 Hz).

The title compound was prepared according to the procedure described in Example 19, employing 3-amino-2-benzoyl-6-chloroindole (Example 1) and ethyl succinyl chloride. p.f .: 156-163 ° C. 1 H-NMR (CDCl 3) d: 9.96 (1 H, sa), 8.39 (1 H, sa), 8.20-8.12 (1 H, m), 7.95-7.77 (2 H, d J = 7.3 Hz), 7.68-7.52 (3H, m), 7.27 (1 H, s), 7.10-7.02 (1 H, m), 4.15 (2H, q, J = 7.0 Hz), 2.74 (4H, s), 1.23 (3H, t, J = 7.0 Hz). • 10 EXAMPLE 57 2-Benzoyl-6-chloro-3- (succinamoylamino) indole A solution of 2-benzoyl-6-chloro-3 - [(3-ethoxycarbonyl) propionamelamino] dol (Example 56, 600 mg, 1.5 mmol) in ammonia solution (10% in ethanol, 15 ml) was added. stirred for 16 hours. The • Resulting solids were collected by filtration and recrystallized from methanol to yield 150 mg (27%) of the title compound as a yellow solid. 20 p.f .: 258-263 ° C. 1 H-NMR (CDCl 3) d: 11.82 (1H, sa), 9.72 (1H, sa), 7.78-7.68 (2H, m), 7.67-7.58 (2H, m), 7.57-7.46 (2H, m), 7.45. (1H, d, J = 7.3 Hz), 7.24 (1 H, sa), 7.10 (1 H, dd, J = 1.8, 8.8 Hz), 6.73 (1 H, sa), 2.20-2.07 (4H, m) . • -t? ^ EXAMPLE 58 (S) - (-) -3- (2-Acehoxypropionyl) amino-2-benzoyl-6-chloroindole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-2-benzoyl-6-chloroindole (Example 1) and (S) - (-) - 2-acetoxypropionyl chloride. p.f .: 80-85 ° C. 1 H-NMR (CDCl 3) d: 10.81 (1 H, sa), 8.37 (1 H, d, J = 8.8 Hz), 8.31 (1 H, sa), 7.82-7.77 (2 H, m), 7.70-7.53 ( 3H, m), 7.29 (1 H, d, J = 1.5 Hz), 7.12 (1 H, dd, J = 1.5, 8.8 Hz), 5.44 (1 H, q, J = 7.0 Hz), 2.33 (3H, s), 1.61 (3H, d, J = 7.0 Hz). [a] 23D- 42.30 (MeOH, c = 0.87) EXAMPLE 59 (S) - (+) - 2-Benzoyl-6-chloro-3-r (2-hydroxypropionyl.amino1indole A solution of (S) - (-) - 3- (2-acetoxipropionylamino) -2-benzoyl-6-chloroindole (example 58, 580 mg, 1.5 mmol) and potassium carbonate (2.0 g, 14 mmol) in ethanol (30 g. ml) and water (10 ml), was stirred for 2 h. The mixture was concentrated and extracted with ethyl acetate (50 ml x 2). The organic extracts were dried (MgSO) and concentrated to give a yellow amorphous solid. Recrystallization from ethyl acetate / hexane gave 420 mg (81%) of the title compound as a yellow solid. p.f .: 185-190 ° C. 1 H-NMR (CDCl 3) d: 11.72 (1 H, sa), 10.40, (1 H, sa), 7.96 (1 H, d, J = 8.8 Hz), 7.83-7.75 (2 H, m), 7.70-7.52 (3H, m), 7.45 (1 H, d, J = 1.8 Hz), 7.10 (1 H, dd, J = 1.8, 8.8 Hz), 5.89 (1 H, sa), 4.14-4.00 (1 H, m ), 1.12 (3H, d, J = 7.0 Hz). [a] 23D + 17.53 (MeOH, c = 0.73). • EXAMPLE 60 3- 2-Acetoxyisobutyrylamino) -2-benzoyl-6-chloroindole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-2-benzoyl-6- • 10-chloroindole (Example 1) and 2-acetoxybutyryl chloride. p.f.:162-165°C. 1 H-NMR (CDCl 3) d: 10.78 (1 H, sa), 8.36 (1 H, d, J = 9.2 Hz), 8.28 (1 H, sa), 7.85-7.76 (2 H, m), 7.68-7.53 ( 3H, m), 7.26 (1 H, d, J = 1.8 Hz), 7.08 (1 H, dd, J = 1.8, 9.2 Hz), 2.21 (3H, s), 1.75 (61-1, s).

EXAMPLE 61 2-Benzoyl-6-chloro-3-, 2-hydroxyisobutyrylamino) indole • The title compound was prepared according to the procedure described in Example 59, starting with 3- (2-20). acetoxyisobutyrylamino) -2-benzoyl-6-chloroindole (example 60). mp: 234-238 ° C 1 H-NMR (DMSO-de) d: 11.66 (1 H, sa), 10.44 (1 H, sa), 7.97 (1 H, d, J = 8.8 Hz), 7.83-7.76 ( 2H, m), 7.70-7.50 (3H, m), 7.45 (1 H, d, J = 1.5 Hz), 5.71 (1 H, s), 7.08 (1 H, dd, J = 1.5, 8.8 Hz), 1.20 (6H, s).

EXEMP Qffi * S phythe S- 3-Acetylamino-6-chloro-2- (thiophene-2-carbonyl) indole Step 1. 3-Amino-6-chloro-1- (ethoxycarbonyl) -2- (thiophene-2-carboniDindol) The title compound was prepared according to the procedure described in step 2 of example 1, from 4- chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2- (bromoacetyl) thiophene (Steinkopt, Justus Liebig Ann. Chem., 1923, 430, 103). 1 H-NMR (CDCl 3) d. 8.27 (1 H, d, J = 1.8 Hz), 7.62-7.40 (3H, m), 7.30 (1 H, dd, J = 1.8, 8.4 Hz), 7.15-7.05 (1 H, m), 5.70 (2H , s), 3.97 (2H, q, J = 7.3 Hz), 0.94 (3H, t, J = 7.3 Hz).

Step 2. 3-Acetylamino-6-chloro-1- (ethoxycarbonyl) -2- (thiophene-2-carboniPindo! The title compound was prepared according to the procedure described in step 1 of example 2 (procedure A ), from 3-amino-6-chloro-1- (ethoxycarbonyl) -2- (thiophene-2-carbonyl) indole (step 1). 1H-NMR (CDCl 3) d: 8.94 (1H, sa ), 8.24 (1 H, d, J = 1.5 Hz), 7.90 (1 H, d, J = 8.4 Hz), 7.69 (1 H, dd, J = 1.1, 5.1 Hz), 7.55 (1 H, J = 1.1, 4.0 Hz), 7.31 (1 H, dd, J = 1.8, 8.8 Hz), 7.13 (1 H, d, J = 4.8, 5.1 Hz), 4.10 (2 H, q, J = 7.3 Hz), 2.24 ( 3H, s), 1.03 (3H, t, J = 7.3 Hz).

The titol compound was prepared according to the procedure described in step 2 of example 2 (method A), starting from 3-acetylamino-6-chloro-1- (ethoxycarbonyl) -2- (thiophene-2-) carbonyl) indole (stage 2). p.f .: 228-231 ° C. 1 H-NMR (CDCl 3) d: 10.10 (1 H, sa), 8.40 (1 H, sa), 8.25 (1 H, d, J = 9.2 Hz), 7.86 (1 H, dd, J = 1.1, 3.7 Hz ), 7.77 (1 H, dd, J = 1.1, 5.1 Hz), 7.34 (1 H, d, J = 1.8 Hz), 7.27 (1 H, dd, 3.7, 5.1 Hz), 7.12 (1 H, dd, J = 1.8, 8.8 Hz), 2.29 (3H, m). IR (KBr) v: 1660, 1560, 1440, 1325, 1250 cm "1 EXAMPLE 63 3-Acetylamino-6-chloro-2- (2-furoyl) indole Step 1. 3-Amino-6-chloro-1- (ethoxycarbonyl-2- (2-fluoride) The title compound was prepared according to the procedure described in step 2 of example 1, from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2-bromoacetylfuran (prepared according to the procedure of S. Kajigaeshi et al., Bull, Chem. Soc. Jpn., 1987 , 60, 1159-1160), tic: Rf = 0.4 (33% ethyl acetate in hexanes) Step 2. 3-Acetylamino-6-chloro-1 - (ethoxycarbonyl) -2- (2-furoyl) indole The title compound was prepared according to the procedure described in step 1 of example 2 (procedure A) , from 3-amino-6-chloro-1- (ethoxycarbonyl) -2- (2-furoyl) indole (step 1). 1 H-NMR (CDCl 3) d: 9.21 (1 H, sa), 8.26 (1 H, d, J = 1.8 Hz), 7.97 (1 H, d, J = 8.8 Hz), 7.60 (1 H, dd, J = OJ, 1.8 Hz), 7.31-7.26 (2H, m), 6.59 (1 H, dd, J = 1.5, 3.7 • Hz), 4.13 (2H, q, j = 7.2 Hz), 2.26 (3H, s), 1.07 (3H, t, J = 7.2 Hz).

Step 3. 3-Acetylamino-6-chloro-2- (2-furoyl) indole The title compound was prepared according to the procedure described in step 2 of example 2 (procedure A), starting from 3-acetylamino- 6-chloro-1- (ethoxycarbonyl) -2- (2-furoyl) indole (step 2) mp: 227- • 10-228 ° C. 1 H-NMR (CDCl 3) d: 10.72 (1 H, sa), 9.42 (1 H, sa), 8.42 (1 H, J = 9.2 Hz), 7J8 (1 H, dd, J = 0J, 1.8 Hz), 7.47 (1 H, dd, J = 0J, 3J Hz), 7.37 (1 H, d, J = 1.5 Hz), 7.08 (1 H, dd, J = 1.8, 8.8 Hz), 6J1 (1 H, dd, J = 1.6, 3.5 Hz), 2.32 (3H, s). IR (KBr) v: 3450, 1690, 1620, 1600, 1580, 1570, 1480, 1460, 1340, 1260, 1200, 900, 770, 630 cm "1. EXAMPLE 64 3-Amino-6-chloro-2- (nicotinoil) indole Step 1. 3-Amino-6-chloro-1-ethoxycarbonyl-2- (nicotinol) indole The title compound was prepared according to the procedure described in step 2 of example 1, starting from 4 chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 3- (bromoacetyl) pyridine bromohydrate (H. McKennis et al., J. Org. Chem., 1963, 387). 1 H- NMR (CDCl 3) d: 8.95 (1 H, dd, J = OJ, 2i / 4z), 8J0 (1 H, dd, J = 1.8, 4.8 Hz), 8.23 (1 H, d, J = 1.5 Hz), 8.03-7.9§ (lfH, m), 7.57 (1 H, d, J = 8.4 Hz), 7.41-7.28 (2H, m), 6.08 (2H, sa), 3.87 (2H, q, J = 7.0 z) , 0.92 (3H, t, J = 7.0 Hz). * Step 2. 3-Amino-6-chloro-2- (nicotinoyl) in: dol The title compound was prepared according to the procedure described in step 3 of example 1, starting from 3-amino-6- chloro-2- (nicotinoyl) -1- (ethoxycarbonyl) indole (step 1). p.f .: 188-189 ° C. 1 H-NMR (CDCl 3) d: 9.09 (1 H, dd, J = 0 J, 2.2 Hz), 8 J 2 (1 H, dd, J = 1.8, 5.1 Hz), 8.12 (1 H, ddd, J = 1.8, 2.2 , 7.7 Hz), 8.01 (1 H, sa), 7.55 (1 H, d, J = 8.4 Hz), 7.47 (1 H, ddd, J = 0J, 4.8, 7.7 Hz), 7.24 (1H, d, J = 1.1 Hz), 7.05 (1 H, dd, J = 1.8, 8.8 Hz), 5.80 (2H, sa).

EXAMPLE 65 3-Acetylamino-6-chloro-2- (nicotinoyl) indole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (nichotinoyl) indole (Example 64). p.f .: 213-214 ° C. 1 H-NMR (DMS06) d: 11.90 (1 H, sa), 9.83 (1 H, sa), 8.82 (1 H, d, J = 2.2 Hz), 8.76 (1 H, dd, J = 1.7, 4.9 Hz ), 8.09-8.01 (1 H, m), 7.64 (1 H, d, J = 8.8 Hz), 7.54 (1 H, dd, J = 4.9, 7.9 Hz), 7.47 (1 H, d, J = 1.5 Hz), 7.13 (1 H, dd, J = 1.8, 8.8 Hz), 1.64 (3H, s), IR (KBr) v: 3300, 1730, 1680, 1590, 1580, 1540, 1440, 1310, 1250, 1230 , 920, 750 cm "1.

AXIS P c 6 3-Amino-6-chloro-2- (isonicotyl) nol Step 1. 3-Amino-6-chloro-1- (ethoxycarbonyl) -2- (isonicotinoyl) nol The title compound was prepared according to the procedure described in step 2 of the example 1, from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 4- (bromoacetyl) pyridine hydrobromide (A. Taurinis and A. Blage, J. Heterocycl. Chem., 1970, 7 , 1137-141). 1 H NMR (CDCl 3) d: 8 J 5 - 8 J 3 (2 H, m), 8.24 (1 H, d, J = 1.5 Hz), 7.57-7.54 (3 H, m), 7.33 (1 H, dd, J = 1.8, 8.4 Hz), 6.04 (2H, sa), 3.82 (2H, q, J = 7.0 Hz), 0.93 (3H, t, J = 7.0 Hz).

Step 2. 3-Amino-6-chloro-2- (sonicotinoyl) indole The title compound was prepared according to the procedure described in step 3 of example 1, starting with 3-amino-6 -chloro-1- (ethoxycarbonyl) -2- (sonicotinoyl) indole (step 1). p.f .: 266-267 ° C. 1 H-NMR (CDCl 3) d: 8.96-8.82 (2H, m), 7.64-7.62 (2H, m), 7.55. (1 H, d, J = 8.4 Hz), 7.44 (1 H, s a), 7.24 (1 H, d, J = 1.5 Hz), 7.06 (1 H, dd, J = 1. 8, 8.8 Hz), 5.80 (2H, s a).

EXAMPLE 67 3-Acetylamino-6-chloro-2- (isonicotinoyl) indole The title compound was prepared according to the procedure described in example 19, using 3-amino-6-chloro-2- (sonicotinoyl) indol (example 66). p.f .: 262-264 ° C. 1 H-NMR (DMSO-d 6): 11.90 (1 H, sa), 9.79 (1 H, sa), 8.77-8.74 (2 H, m), 7.66 (1 H, d, J = 8.8 Hz), 7.58-7.55 (2H, m), 7.46 (1 H, d, J = 1.8 Hz), 7.13 (1 H, dd, J = 1.8, 8.8 Hz), 1.64 (3H, s).

EXAMPLE 68 3-Amino-6-chloro-2- (4-chloropyridine-2-carbonyl) nol Step 1. 3-Amino-6-chloro-2- (4-chloropyridine-2-carbonyl) -1- (ethoxycarbonyl) indole The title compound was prepared according to the procedure described in step 2 of Example 1, starting with 4-chloro-2- (ethoxycarbonylamino) benzonyl ether (example 1, step 1) and 2- (bromoacetyl) -4-chloropyridine hydrobromide *. 1 H-NMR (CDCl 3) d: 8.50 (1 H, d, J = 5.5 Hz), 8.20 (1 H, d, J = 1.8 Hz), 8.06 (1 H, d, J = 2.6 Hz), 7.52 (1 H, d, J = 8.4 Hz), 7.38 (1 H, dd, J = 1.8, 5.1 Hz), 7.25 (1 H, dd, J = 1.8, 8.4 Hz), 6.06 (2H, sa), 3.86 (2H , q, J = 7.0 Hz), 0.96 (3H, t, J = 7.0 Hz). * 2- (Bromoacetyl) -4-chloropyridine hydrobromide was prepared »? * > i3® as indicated below; 4-Chloro-2-pyridinecarbonylide: To a mixture of 4-chloropyridine N-oxide (5.00 g, 38.6 mmol) and trimethylsilyl cyanide (4.84 g, 46.3 mmol) in dichloromethane (60 ml), cooled to 0 °. C, N, N-dimethylcarbamoyl chloride (3.8 ml, 40.5 mmol) was added dropwise. The mixture was allowed to warm to room temperature and was stirred for 16 h. The mixture was cooled to 0 ° C and a 30% aqueous solution of K2C03 (100 mL) was added. The crude product was extracted with dichloromethane (100 ml x 2), the organic extracts were dried (MgSO 4) and evaporated to give 4-chloro-2-10 pyridinecarbonitrile (5.35 g, 100%). 1 H-NMR (CDCl 3) d: 8.63 (1 H, d, J = 4.8 Hz), 7 J 2 (1 H, d, J = 2.6 Hz), 7.55 (1 H, dd, J = 1.8, 5.1 Hz). 2-Acetyl-4-chloropyridine: To a solution of 4-chloro-2-pyridinecarbonitrile (5.35 g, 38.6 mmol) in benzene (50 ml) and ether (50 ml), cooled to 0 ° C, was added drop drop for 20 minutes a 2M solution of MeMgl in ether (23 ml, 46.3 mmol). After 0.5 h, the mixture was allowed to warm to room temperature and stirring was continued for 3 hours. The mixture was cooled to 0 ° C and 2M aqueous HCl (100 ml) was added. The mixture was made basic with saturated aqueous sodium bicarbonate (-80 ml) and the organic layer was separated and dried (MgSO). After removing the solvent, the The residue was purified by flash chromatography eluting with ethyl acetate / hexane (15) to yield 3.60 g (60%) of 2-acetyl-4'-chloropyridine. 1 H NMR (DMSO-de) d: 8.59 (1 H, d, J = 5.1 Hz), 8.04 (1 H, d, J = 1.8 Hz), 7.47 (1 H, dd, J = 1.8, 5.1 Hz), 2J2 (3H, s). á2í2áfe = 5sái: í. _-S-_. "2- (Bromoacetyl) -4-chloropyridine hydrobromide: 2- (Bromoacetyl) -4-chloropyridine hydrobromide was prepared from 2-acetyl-4'-chloropyridine according to the procedure of H. Mckennis, Jr., LB Turnbull, ER Bowman and E. Tamaki (in J. Org. Chem., 1963, 28, 383-387). 1H, NMR (DMSO-de) d: 8.74 (1H, d, J = 5.5 Hz), 8.05 (1 H, d, J = 1.8 Hz), 7.88 (1 H, dd, J = 2.2 and 5.5 Hz), 5.02 (2H, s).

Step 2. 3-Amino-6-chloro-2- (4-chloropyridine-2-carbonyl) indole The title compound was prepared in accordance with The procedure described in step 3 of Example 1, starting from 3-amino-6-chloro-2- (4-chloropyridine-2-carbonyl) -1- (ethoxycarbonyl) indol (step 1) ). p.f .: 234-235 ° C. 1 H NMR (DMSO-d 6) d: 10.94 (1 H, sa), 8.78 (1 H, d, J = 5.5 Hz), 8.14 (1 H, d, J = 2.2 Hz), 7.92 (1 H, d, J = 8.4 Hz), 7.80 (1 H, dd, J = 1.5, 5.1 Hz), 7.51 (1 H, d, J = 1.8 Hz), 6.93 (1 H, dd, J = 1.8, 8.8 Hz). 15 The signal due to NH2 was not observed.

EXAMPLE 69 3-Acetylamino-6-chloro-2- (4-chloropyridine-2-carbonyl) indole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (4-chloropyridine-2-carbonyl) indole (Example 68). p.f .: 201-202 ° C. 1 H NMR (DMSOde): 11.97 (1 H, sa), 10.22 (1 H, sa), 8.75 (1 H, d, J = 5.1 Hz), 8.04 (1 H, d, J = 1.5 Hz), 7.86- 7.79 (2H, m), 7.59 (1 H, d, J = 1.8 Hz), 7.09 (1 H, dd, J = 1.8, 8.8 Hz), 1.96 (3H, s).

EXAMPLE 70 3-Amino-6-chloro-2- (4-methylpyridine-2-carbonyl) indole Step 1. 3-Amino-6-chloro-1- (ethoxycarbonyl) -2- (4-methylpyridine-2-carbonyndiol) The title compound was prepared in accordance with The procedure described in step 2 of example 1, starting with 4-chloro-2- (ethoxycarbonylamino) benzonitrile (Example 1. step 1) and 2- (bromoacetyl) -4-methylpyridine hydrochloride (FH Case et al. , J. Am. Chem. Soc, 1956, 78, 5842). 1 H NMR (CDCl 3) d: 8.46 (1 H, d, J = 4.8 Hz), 8.22 (1 H, d, J = 1.8 Hz), 7.89 (1 H, s), 7.51 (1 H, d, J = 8.4 Hz), 7.24 (1 H, dd, J = 1.8, 8.4 Hz), 7.20 (1 H, d, J = 4.8 Hz), 5.97 (2 H, s a), 3.80 (2 H, q, J = 7.0 Hz) 2.46 (3 H, s), 0.90 (3 H, t, J = 7.0 Hz).

• Step 2. 3-Amino-6-chloro-2- (4-methy1-pyridine-2-carbonyl) indole The title compound was prepared in accordance with The procedure described in step 3 of Example 1, starting from 3-amino-6-chloro-1- (ethoxycarbonyl) -2- (4-methylpyridine-2-carbonyl) indole (step 1). p.f .: 195- 196 ° C. 1 H NMR (DMSO-d 6) d: 11.11 (1H, s a), 8.59 (1H, d, J = 5.1 Hz), 8.17 (1 H, s), 7.52 (1 H, d, J = 8.8 Hz), 7.33 (1 H, d, J = 1.5 Hz), 7.29 (1 H, d, J = 4.8 Hz), 6.96 (1 H , dd, J = 1.8, 8.4 Hz), 6.03 (2Ht s a), 2.48 (3H, s).

EXAMPLE 71 • 3-Acetylamino-6-chloro-2- (4-methylpyridine-2-carbonyl) nol The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (4-methylpyridine-2-carbonyl) dol (Example 70). p.f .: 187-188 ° C. 1 H NMR (DMSOde) d: 12.05 (1 H, s a), 10.48 (1 H, s a), 8.68 (1 H, d, J = 4.8 Hz), 7.94 (1 H, s), • 10 7.85 (1 H, d, J = 8.8 Hz), 7.63 (1 H, d, J = 1.5 Hz), 7.56 (1 H, dd, J = 0.9, 5.0 Hz), 7.07 (1 H, dd, J = 1.8, 8.8 Hz), 2.47 (3H, s), 2.04 (3H, s).

EXAMPLE 72 3-Amino-6-chloro-2- (4-methoxypyridine-2-carbonyl) indole Step 1. 3-Amino-6-chloro-1- (ethoxycarbonyl) -2- (4-methoxypyridine) -2- • carboniDindol The title compound was prepared according to the procedure described in step 2 of example 1, starting with 4-chloro-2- (ethoxycarbonylamino) benzonitrile (Example 1, step 1) and hydrobromide 2. - (bromoacetyl) -4-methoxypyridine *.? NMR (DMSO-de) d: 8.42 (1 H, d, J = 5.9 Hz), 8.22 (1 H, d, J = 1.8 Hz), 7.61 (1 H, d, J = 2.9 Hz), 7.51 (1 H, d, J = 8.4 Hz), 7.27-7.23 (1 H, m), & i, i * l 6.89 (1 H, dd, J = 2.6, 5.9 Hz), 5.96 (2H, sa) ', 3.95 (3H, s), 3.84 (2H, q, J = 7.0 Hz), 0.95 (3H, t, J = 7.0 Hz). * The 2- (bromoacetyl) -4-methoxypyridine bromide was prepared as follows; 4-methoxy-2-pyridinecarbonitrile: To a mixture of 4-methoxypyridine N-oxide (5.00 g, 38.6 mmol) and trimethylsilyl cyanide (4.84 g, 46.3 mmol) in diethylmethane (60 ml) cooled to 0 ° C, N, N-dimethylcarbamoyl chloride (3.8 ml, 40.5 mmol) was added dropwise. The mixture was allowed to warm to room temperature and was stirred for 16 hours. The The mixture was cooled to 0 ° C and a 30% aqueous solution of K2C03 (100 ml) was added. The crude product was extracted with dichloromethane (100 ml x 2 ml), the organic extracts were dried (MgSO) and evaporated to give 4-methoxy-2-pyridinecarbonitrile (5.35 g, 100%). ? NMR (CDCl 3) d: 8.51 (1 H, d, J = 5.9 Hz) 7.22 (1 H, d, J = 2.6 Hz), 7.01 (1 H, dd, J = 2.6, 5.9 Hz), 3.91 (3 H, s). 15 2-Acetyl-4-methoxypyridine: To a solution of 4-methoxy-2-pyridinecarbonitrile (5.35 g, 38.6 mmol) in benzene (50 ml) and ether (50 ml) • cooled to 0 ° C, a 2M solution of MeMgl in ether (23 ml, 46.3 mmol) was added dropwise over 20 minutes. After 0.5 h, the mixture was allowed to warm to room temperature and stirring was continued for 2 hours. hours. The mixture was cooled to 0 ° C and 2M aqueous HCl (100 ml) was added. The mixture was made basic with saturated aqueous sodium bicarbonate (-80 ml) and the organic layer was separated and dried (MgSO 4) After removing the solvent, the residue was purified by flash chromatography eluting with EXAMPLE 73 3-Acetylamino-6- chloro-2- (4-methoxypyridine-2-carbonyl) indole The title compound was prepared according to the procedure described in Example 19, using 3-amino-6-chloro-2- (4-methoxypyridine-2-carbonyl) dol (Example 72). p.f .: 207-208 ° C (ethyl acetate)? NMR (DMSO-de) d: 12.09 (1 H, sa), 10.54 (1 H, sa), 8.66 (1 H, d, J = 5.5 Hz), 7.87 (1 H, d, J = 8.8 Hz), 7.64 (1 H, d, J = 1.8 Hz), 7.62 (1 H, d, J = 2.6 Hz), 7.31 (1 H, dd, J = 2.6, 5.9 Hz), 7.06 (1 H, dd, J = 1.8, 8.8 Hz), 3.96 • 10 (3H, s), 2.07 (3H, s).

EXAMPLE 74 6-Chloro-3-isovalerylamino-2- (4-methoxypyridine-2-carbonyl) indole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (4-methoxy-pyridine-2-carbonyl) indole (Example 72) and sodium chloride. isovaleryl mp .: 162-163 ° C (ethyl acetate / hexane). ? NMR (DMSO-de) d: 12.08 (1 H, sa), 10.54 (1 H, sa), 8.66 (1 H, 20 d, J = 5.5 Hz), 7.88 (1 H, d, J = 8.8 Hz) , 7.64 (1 H, d, J = 1.5 Hz), 7.63 (1 H, d, J = 2.6 Hz), 7.31 (1 H, dd, J = 2.6, 5.5 Hz), 7.07 (1 H, dd, J = 1.8, 8.8 Hz), 3.95 (3H, s), 2.24 (2H, s, J = 7.3 Hz), 2.09-2.00 (1 H, m), 0.93 (6H, d, J = 6.6 Hz), EXAMPLE 75 3-Amino-6-chloro-2- (2-tiazolyl) indole Step 1. 3-Amino-6-chloro-1- (ethoxycarbonyl) -2- (2-tiazolidol) The title compound was prepared according to the procedure described in step 2 of example 1 , from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (Example 1, step 1) and 2- (bromoacetyl) thiazole hydrobromide (A. Dondoni, A. Marra and P. Merino, J. Am. Chem. Soc. , 1994, 116, 3324-3336).? NMR (CDCI3) d: 8.22 (1 H, d, J = 1.8 Hz), 7.99 (1 H, • 10 d, J = 3.3 Hz), 7.60 (1 H, d, J = 3.3 Hz), 7.52 (1 H, d, J = 8.4 Hz), 7.23 (1 H, dd, J = 1.8, 8.4 Hz) , 6.21 (2H, s), 4.00 (2H, q, J = 7.1 Hz), 0.94 (3H, t, J = 7.1 Hz).

Step 2. 3-Amino-6-chloro-2- (2-thiazolyl) indole The title compound was prepared according to the procedure described in step 3 of example 1, starting from 3-amino-6-chloro -1- (ethoxycarbonyl) -2- (2-thiazolyl) idol (step 1). p.f .: 233-234 ° C.

•? NMR (CDCl 3) d: 10.64 (1 H, sa), 8.22 (/ 1 H, d, J = 3.3 Hz), 8.16 (1 H, d, J = 3.0 Hz), 7.93 (1 H, d, J = 8.4 Hz), 7.60-7.35 (3H, sa), 6.94 (1 H, dd, J = 1.8, 8.8 Hz) EXAMPLE 76 3-Acetylamino-6-chloro-2- (2-thiazolyl) indole • The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (2-thiazolyl) indole (Example 75). p.f .: 220-221 ° C? NMR (DMSO-d6): 11.87 (1 H, s), 10.60 (1 H, s), 8.34-8.31 (2H, m), 7.91 (1 H, d, J = 8.8 Hz), 7.71 (1 H, d, J = 1.8 Hz), 7.08 (1 H, dd, J = 1.8, 8.8 Hz), 2.15 (3H, s). • 10 EXAMPLE 77 3-Amino-6-chloro-2-r2- (5-methylfuroyl? Lindol Step 1. 3-amino-6-chloro-1- (ethoxycarbonyl) -2-r2- (5-methylphuropanediol) The title compound was prepared according to the procedure described in step 2 of Example 1, starting from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (Example 1, step 1) and 2- (bromoacetyl) -5- # methylfuran (KY Novitskyi et al., J. Org. Chem. USSR, 1965, 1, 377-379).

NMR (CDCl 3) d: 8.25 (1 H, d, J = 1.5 Hz), 7.52 (1 H, d, J = 8.4 Hz), 7.24 (1 H, dd, J = 1.8, 8.4 Hz), 7.11 (1 H, d, J = 3.3 Hz), 6.15 (1 H, dd, J = 0.9, 3.3 Hz), 5.82 (2H, sa), 4.05 (2H, q, = 7.0 Hz), 2.36 (3H, s), 1.03 (3H, t, J = 7.0 Hz).

Step 2. 3-Amino-6-chloro-2-r2- (5-roethyl-furoyl.1indol) The title compound was prepared according to the procedure described in step 3 of example 1, starting from 3-amino-6- chloro-1- (ethoxycarbonyl) -2- [2- (5-methyl-furoyl)] indole (step 1), mp: 140-141 ° C. 1 H NMR (CDCl 3) d: 8.69 (1 H, s), 7.50. 1 H, d, J = 8.4 Hz), 7.31 (1 H, d, J = 1.1 Hz), 7.26 (1 H, d, J = 2.9 Hz), 6.97 (1 H, dd, J = 1.5, 8.4 Hz ), 6.22 (1 H, dd, J = 1.1, 3.7 Hz), 5.91 (2H, sa), 2.50 (3H, s).

EXAMPLE 78 10 3-Acetylamino-6-chloro-2-r 2 - (5-methylfuroyl) 1indole The title compound was prepared according to the procedure described in Example 19, using 3-amino-6-chloro-2- "2- (5-methyl-furoyl) indole (Example 77) and acetyl chloride. 209 ° C. 1H NMR (CDCl 3) d: 10.73 (1H, sa), 9.30 (1 H, sa), 8.42 (1 H, d, J = 9.2 Hz), 7.39 (2H, d, J = 1.8 Hz), 7.09 (1 H , dd, J = 1.8, 9.2 Hz), 6.33 (1 H, d, J = 3.3 Hz), 2.57 (3 H, s), 2.31 (3 H, s). • EXAMPLE 79 3-Amino-6-chloro-2- (3-furoyl) indole • Step 1. 3-amino-6-chloro-1-ethoxycarbonyl-2- (3-furoyl) indole The title compound was prepared according to the procedure described in step 2 of example 1, starting from 4-chloro -2- (ethoxycarbonylamino) benzonitrile (Example 1, step 1) and 3-bromoacetylfuran (RA Massy-Westropp and GD Reynolds, Aust. J. Chem., 1966, 19, 891-892). 1 H NMR (CDCl 3) d: 8.24 (1 H, d, J = 1.8 Hz), 7.93 (1 H, s), 7.51. (1 H, d, J = 8.4 Hz), 7.45 (1 H, dd, J = 1.5, 1.8 Hz), 7.30 (1 H, dd, J = 1.8, 8.4 Hz), 6.78 (1 H, dd, J = 0.7, 1.1 Hz), 5.72 (2H, sa), 4.06 (2H, q, J = 7.3 Hz), 1.05 (3H, t, J = 7.3 Hz).

Step 2. 3-Amino-6-chloro-2- (3-furoidol) The title procedure was prepared according to the procedure described in step 3 of example 1, starting from 3-amino-6. - chloro-1-ethoxycarbonyl-2- (3-furoyl) indole (step 1) mp: 113-114 ° C (dichloromethane / hexane)? NMR (CDCl 3) d: 8.08 (1 H, dd, J = 0.7, 1.5 Hz), 7.70 (1 H, sa), 7.51 (1 H, d, J = 8.8 Hz), 7.51 (1 H, dd, J = 1.5, 1.8 Hz), 7.27 (1 H, d, J = 2.2 Jz), 7.03 (1 H, dd, J = 1.8, 8.8 Hz), 6.87 (1 H, dd, J = 1.8, 0.7 Hz), 5.70 (2H, s a).

EXAMPLE 80 3-Acetylamino-6-chloro-2- (3-furoyl) indole The title compound was prepared according to the procedure described in Example 19, starting from 3-amino-6-chloro-2- (3-furoyl) indole (Example 79) and acetyl chloride. mp .: 217-219 ° C (ethyl acetate / hexane). 1 H NMR (CDCl 3) d: 10.04 (1 H, sa), 8.25 (1 H, sa), 8.21 (1 H, sa), 8.12 (1 H, dd, J = 1.1, 1.5 Hz), 7.59 (1 H , dd, J = 1.5, 1.8 Hz), 7.32 (1 H, d, J = 1.8 Hz), 7.12 (1 H, dd, J = 1.8, 8.8 Hz), 6.89 (1 H, dd, J = 0.7, 1.8 Hz), 2.29 (3H, s).

EXAMPLE 81 3-Amino-6-chloro-2- (3-phenyl-5-isoxazoyl) indole Step 1. 3-Amino-6-chloro-1- (ethoxycarboniP-2- (3-phenyl] -5-issoxazole Pindol The title compound was prepared according to the procedure described in step 2 of example 1, starting from of 4-chloro-2- (ethoxycarbonylamino) benzonitrile (Example 1, step 1), and 5- (bromoacetyl) -3-phenyl isoxazole. 1 H NMR (CDCl 3) d: 8.27 (1 H, d, J = 1.8 Hz) , 7.89-7.84 (2H, m), 7.56 (5H, m), 7.30 (1 H, dd, J = 1.8, 8.4 Hz), 6.18 (2H, s), 4.13 (2H, q, J = 7.2 Hz) , 1.10 (3H, t, J = 7.2 Hz).

Step 2. 3-Amino-6-chloro-2-.3-phenlr-5-isoxazoPPndol The title compound was prepared according to the procedure described in step 3 of example 1, starting from 3-Amino-6-chloro-1- (ethoxycarbonyl) -2- (5-phenyl-3-isoxazoyl) indole (step 1). p.f .: 241-242 ° C. 1 H NMR (CDCl 3) d: 8.81 (1 H, s a), 7.91-7.86 (2H, m), 7.56-7.49 (4H, m), 7.38 (1 H, s), 7.32 (1 H, d, J = 1.5 Hz), 7.03 (1 H, dd, J = 1.5, 8.8 Hz), 6. 23 (2H, s a).

EXAMPLE 82 • 10 3-Acetylamino-6-chloro-2- (3-phenyl-5-isoxazoyl) indole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (3-phenyl-5-isoxazoyl) indole (Example 81). p.f .: 209-210 ° C. NMR (CDCI3) d: 10.65 (1 H, sa), 9.52 (1 H, sa), 8.49 (1 H, d, J = 9.2 Hz), 7.92-7.86 (2H, m), 7.56-7.52 (3H, m), 7.45 (1 H, s), 7.40 (1 H, d, J = 1.8 Hz), 7.11 (1 H, dd, J = 1.8, 9.2 Hz), • 2.36 (3H, s).

EXAMPLE 83 3-Amino-6-chloro-2- (phenylacetyl) indole Step 1. 3-Amino-6-chloro-1- (ethoxycarboniP-2- (phenollacetPindol) The title compound was prepared according to the procedure described in step 2 of example 1, starting from 4 -chloro-2- (ethoxycarbonylamino) benzonitrile (Example 1, step 1) and 2-chloro-2'-phenylacetone (J. Barluenga, M. Yus, JM Concellon, P. Bernad, J. Org. Chem., 1983, 48, 3116-3118). NMR (CDCl 3) d: 8.07 (1 H, d, J = 1.8 Hz), 7.41 (1 H, d, J = 8.4 Hz), 7.34 (1 H, d, J = 4.4 Hz), 7.31-7.16 (5H, m), 5.89 (2H, s, a), 4.43 (2H, q, J = 7.2 Hz), 4.02 (2H, s), 1.42 (3H, t, J = 7.2 Hz).

Step 2. 3-Amino-6-chloro-2- (phenylacetyl) nol The title compound was prepared according to the procedure described in step 3 of example 1, starting from 3-amino-6-chloro -1- (ethoxycarbnoyl) -2- (phenylacetyl) indole (step 1). p.f .: 204-205 ° C 1H NMR (CDCI3) d: 7.46 (1 H, d, J = 8.4 Hz), 7.40-7.26 (6H, m), 7.17 (1 H, sa), 6.99 (1 H, da, J = 8.4 Hz), 5.51 ( 2H, sa), 4.07 (2H, s).

EXAMPLE 84 3-Acetylamino-6-chloro-2- (phenylacetyl) nol The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (phenylacetyl) indole (Example 83). mp: 259-259 ° C NMR (DMSO-d6) d: 11.76 (1 H, sa), 9.98 (1 H, sa), 7.63 (1 H, d, J = 8.8 Hz), 7.43 (1 H, d , J = 1.5 Hz), 7.36-7.22 (5H, m), 7.09 (1 H, dd, J = 1.8, 8.8 Hz), 4.27 (2H, s), 2.16 (3H, s). • 10 EXAMPLE 85 2-Acetyl-3-amino-6-chloroindole Step 1. 2-Acetyl-3-amino-6-chloro-1- (ethoxycarboniPndol) The title compound was prepared in accordance with The procedure described in step 2 of Example 1, starting with 4-chloro-2- (ethoxycarbonylamino) benzonitrile (Example 1, step 1) and 2-bromoacetone. 1 HOUR • NMR (DMSO-de) d: 8.02 (1 H, d, J = 8.4 Hz), 7.98 (1 H, d, J = 1.8 Hz), 7.40 (1 H, dd, J = 1.8, 8.4 Hz), 7.22 (2H, s, a), 7.44 (2H, q, J = 7.3 Hz), 2.27 (3H, s), 1.40 (3H, t, J = 7.3 Hz). Step 2. 2-Acetyl-3-amino-6-chloroindole The title compound was prepared according to the procedure described in step 3 of Example 1, starting from 2-acetyl-3-amino-6-chloro- 1- (ethoxycarbonyl) indol (step 1). 1 H NMR (DMSO-de) d: 10.60 (1 H, sa), 7.83 (1 H, d, J = 8.4 Hz), 7.24 (1 H, d, J = 1.8 Hz), 6.92 (1 H, J, = 1.8 Hz), 6.44 (2H, sa), 2.40 (3H, s).

EXAMPLE 86 2-Acetyl-3-acetylamino-6-chloroindole The title compound was prepared according to the procedure described in Example 19, employing 2-acetyl-3-amino-6- • 10-chloroindole (Example 85). p.f .: 262-267 ° C. 1 H NMR (DMSO-d 6) d: 11.71 (1 H, sa), 9.90 (1 H, sa), 7.60 (1 H, d, J = 8.8 Hz), 7.41 (1 H, d, J = 1.8 Hz) , 7.09 (1 H, dd, J = 1.8, 8.8 Hz), 2.51 (3H, s), 2.16 (3H, s). EXAMPLE 87 • 3-Amino-6-chloro-2-propionylindole Step 1. 3-Amino-6-chloro-1- (ethoxycarbon-P-2-propionyl) -ol 20 The title compound was prepared according to the procedure described in step 2 of example 1, from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (Example 1, step 1) and 2-bromoethyl ethyl ketone:? NMR (CDCl3) d: 7.75-7.67 (2H, m), 7.35 (1H, dd, J = 8.4, 2.2 Hz), 4.45 (2H, sa), 4.30-4.10 (2H, m), 2.60-2.40 (2H, m), 1.35-1.1 (6H, m).

Step 2. 3-Amino-6-chloro-2-propionylindole • The title compound was prepared according to the procedure described in step 3 of example 1, starting from 3-amino-6-chloro-1- (ethoxycarbonyl) -2-propionylindole (step 1). p.f .: 144-146 ° C. 1 H NMR (DMSO-d 6) d: 9.15 (1 H, sa), 7.52 (1 H, d, J = 8.4 Hz), 7.27 (1 H, d, J = 1.8 Hz), 6.95 (1 H, dd, J = 1.8, 8.4 Hz), 5.53 (2H, sa), 2.80 (2H, q, J = 7.3 Hz), 1.25 (3H, t, J = 7.3 Hz). • 10 EXAMPLE 88 3-Acetylamino-6-chloro-2-propionylindole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2-propionylindole (Example 87) and acetyl chloride. p.f .: > 270 ° C. NMR (DMSO-d6) d: 11.72 (1 H, sa), 9.93 (1 H, sa), 7.59 (1 H, d, J = 8.4 Hz), 7.43 (1 H, s), 7.07 (1 H, d, J = 8.4 Hz), 2.94 (2H, q, J = 7.0 Hz), 2.15 (3H, s), 1.09 (3H, t, J = 7.0 Hz).

EXAMPLE 89 3-Amino-6-chloro-2-trimethylacetyindol Step 1. 3-Amino-6-chloro-1- (ethoxycarboniP-2-trimethylacetylindol) The title compound was prepared according to the procedure described in step 2 of example 1, starting with 4-chloro-2- (ethoxycarbonylamino) ) benzonitrile (Example 1, step 1) and 2-bromoethyl ferc-butyl ketone:? NMR (CDCI3) d: 7.60 (1 H, d, J = 8.8 Hz), 7.37 (1 H, dd, J = 1.8, 8.8 Hz), 7.28 (1H, d, J = 1.8 Hz), 4.59 (2H, sa), 4.28-4.10 (2H, m), 1.31-1.19 (12H, m).

Step 2. 3-Amino-6-chloro-2-trimethylacetylindole The title compound was prepared according to the procedure described in step 3 of example 1, starting from 3-amino-6-chloro-1- ( ethoxycarbonyl) -2-trimethylacetylindole (step 1). p.f .: 132-134 ° C. 1 H NMR (CDCl 3) d: 7.60 (1 H, sa), 7.47 (1 H, d, J = 8.4 Hz), 7.26 (1 H, d, J = 1.8 Hz), 7.00 (1 H, dd, J = 1.8, 8.4 Hz), 5.76 (2H, sa), 1.40 (9H, s).

EXAMPLE 90 3-Acetylamino-6-chloro-2-trimethylacetyindol The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2-trimethylacetylindole (Example 89) and acetyl chloride. p.f .: 190-193 ° C. 1 H NMR (CDCl 3) d: 10.46 (1H, sa), 8.40 (1 H, sa), 8.22 (1 H, d, J = 9.2 Hz), 7.29 (1 H, s), 7.05 (1 H, d, J = 9.2 Hz), 2.29 (3H, s), 1.42 (9H, s).

EXAMPLE 91 3-Acetylamino-6-chloro-2- (pyrazine-2-carbonyl) indole Step 1. 3-Amino-6-chloro-1- (ethoxycarbon-P-2- (pyrazine-2-carboniPindol) The title compound was prepared according to the procedure described in step 2 of example 1, starting from of 4-chloro-2- (ethoxycarbonylamino) benzonitrile (Example 1, step 1) and 2- (bromoacetyl) prazrazine (prepared according to the procedure of FH Case et al., J. Am. Chem. Soc, 1956, 78, 5842).? NMR (CDCI3) d: 9.26 (1 H, d, J = 1.5 Hz), 8.67 (1 H, d, J) 2.6 Hz), 8.56 (1 H, dd, J = 1.5, 2.6 Hz), 8.21 (1 H, d, J = 1.8 Hz), 7.55 (1 H, d, J = 8.4 Hz), 7.27 (1 H, dd , J = 1.5, 8.4 Hz), 6.18 (2H, sa), 3.87 (2H, q, J = 7.0 Hz), 0.93 (3H, t, J = 7.0 Hz).

Step 2. 3-Acetylamino-6-chloro-1- (ethoxycarboniP-2- (pyrazine-2-carboniPindol) The title compound was prepared according to the procedure described in step 1 of example 2 (method A), from n of 3-amino-6-chloro-1- (ethoxycarbonyl) -2- (pyrazine-2-carbonyl) idol (step 1). tic: Rf = 0.4 (50% acetone in hexanes).

Step 3. 3-Acetylamino-6-chloro-2- (pyrazine-2-carboniPndol) The title compound was prepared according to the procedure described in step 2 of example 2 (method A), starting from 3- acetylamino-6-chloro-1 - (ethoxycarbonyl) -2- (pyrazine-2-carbonyl) dol (step 2) mp: 269-271 ° C. NMR (DMSO-de) d: 11.92 (1H, sa ), 10.10 (1 H, sa), 9.10 (1 H, d, J = 1.5 Hz), 8.89 (1 H, d, J = 2.2 Hz), 8J9 (1 H, dd, J = 1.5, 2.2 Hz) , 7J7 (1 H, d, J = 8.8 Hz), 7.54 (1 H, d, J = 1.5 Hz), 7.11 (1 H, dd, J = 1.8, 8.8 Hz), 1.84 (3H, s).

EXAMPLE 92 3-Acetylamino-6-chloro-2- (2-naphthoyl) nol Step 1. 3-Amino-6-chloro-1- (ethoxycarbonyl) -2- (2-naphthoPindol) The title compound was prepared according to the procedure described in step 2 of example 1, a from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2-bromo-2'-acetonaphthone: Rf = 0.8 (50% ethyl acetate in hexanes).

Step 2. 3-Acetylammon-6-chloro-1- (ethoxycarboniP-2- (2-naphthoyl) indole The title compound was prepared according to the procedure described in step 1 of example 2 ( procedure A), from 3-amino-6-chloro-1- (ethoxycarbonyl) -2- (2-naphthoyl) indole (step 1). tic: Rf = 0.6 (50% ethyl acetate in hexanes).

Step 3. 3-Acetylamino-6-chloro-2- (2-naphthoiDindol) The title compound was prepared according to the procedure described in step 2 of example 2 (method A), starting from 3-acetylamino no-6-chloro-1- (ethoxycarbonyl) -2- (2-naphthoyl) indole (step 2) .pf: 167-169 ° C. 1H NMR (CDCl 3) d: 9.87 / 1 H, sa), 8.32 ( 2H, a), 8.24 (1 H, d, J = 8.8 Hz), 8.07-7.80 (4H, m), 7.70-7.56 (2H, m), 7.30 (1 H, a), 7.12 (1 H, dd , J = 1.8, 8.8 Hz), 2.23 (3H, s).

EXAMPLE 93 3-Amino-6-chloro-2- (cyclohexanecarbonyl) indole Step 1. 3-Amino-6-chloro-2- (cyclohexanecarbon-P-1- (ethoxycarboniPindol) The title compound was prepared according to the procedure described in step 2 of example 1, starting from 4-chloro-2. - (ethoxycarbonylamino) benzonitrile (Example 1, step 1) and 2- bromoacetylcyclohexane (Lotfield, Schaad, J. Am. Chem. Soc, 1954, 76, 35). ? NMR (CDCl 3) d: 8.14 (1 H, d, J = 1.8 Hz), 7.45 (1 H, d, J = 8.4 Hz), 7.26 (1 H, dd, J = 1.8, 8.4 Hz), 5.66 (2 H , a), 4.44 (2H, q, J = 7.0 Hz), 2.95-2J2 (1 H, m), 2.00-1.10 (13H, m).

Step 2. 3-Amino-6-chloro-2- (cyclohexanecarboniPindol) The title compound was prepared according to the procedure described in step 3 of example 1, starting from 3-amino-6-chloro-2-. (cyclohexanecarbonyl) -1- (ethoxycarbonyl) idol (step 1). 10 1 H NMR (CDCl 3) d: 7.66 (1 H, sa), 7.49 (1 H, d, J = 8.4 Hz), 7.26 (1 H, s), 7.02 (1 H, d, J = 8.4 Hz), 5.50 (2 H, s a), 2.88-2 J2 (1 H, m), 2.00-1.20 (10H, m).

EXAMPLE 94 15 3-Acetylamino-6-chloro-2- (cyclohexanecarbonyl) indole • The title compound was prepared according to the procedure described in Example 19, starting from 3-amino-6-chloro-2- (cyclohexanecarbonyl) indole (Example 93) and acetyl chloride. p.f .: 198 ° C. 1 HOUR NMR (CDCl 3) d: 9.96 (1 H, sa), 8.49 (1 H, a) 8.21 (1 H, d, J = 8.4 Hz), 7.28 (1 H, s), 7.06 (1 H, d, = 8.1 Hz), 3.05-2.85 (1 H, m), 2.29 (3H, s), 2.15-1.20 (10h, m). IR (KBr) v: 1655, 1630, 1570, 1540, 1440 cm "1. t-c-pís-jas *! * - .. --- fr * -_ 3 «*. f "t.

EXAMPLE 95 6-Chloro-2-cyclohexanecarbonyl-3- (isovalerylamine) indole The title compound was prepared according to the procedure described in Example 19, starting with 3-amino-6-chloro-2- (cyclohexanecarbonyl) indole (Example 93) and isovaleryl chloride. p.f .: 209-215 ° C. NMR (DMSO-de) d: 11.6 (1 H, sa), 9.86 (1 H, sa), 7.52 (1 H, d, J = 8.8 Hz) 7.42 (1 H, d, J = 1.8 Hz), 7.07 (1 H, dd, J = 1.8, 8.8 Hz), 3.40-3.19 (1 H, m), 2.32 (2 H, d, J = 7.0 Hz), 2.29-2.08 (1 H, m), 1.92-1.13 ( 10H, m), 1.01 (6H, d, J = 6.6 Hz).

EXAMPLE 96 3-Acetylamino-2-benzoyl-5-nitroindole Step 1. 2- (Ethoxycarbonylamino) -5-nitrobenzonitrile The title compound was prepared according to the procedure described in step 1 of example 1 (process A), starting from 2-amino-5-nitrobenzonitrile. tic: Rf = 0.4 (33% ethyl acetate in hexanes).

Step 2. 3-Amino-2-benzoyl-1- (ethoxycarbonyl) -5-nitroindole The title compound was prepared according to the procedure described in step 2 of example 1, starting from 2- ( ethoxycarbonyl amino) -5-nitrobenzonitrile (step 1). NMR (CDCl 3) d: 8.60 (1 H, d, J = 2.2 Hz), 8.42 (1 H, dd, J = 2.2, 9.2 Hz), 8.33 (1 H, d, J = 9.2 Hz), 7J-7.8 (2H, m), 7.4-7.5 (3H, m), 5.84 (2H, sa), 3J7 (2H, q, J = 7.0 Hz), 0.87 (3H, t, J = 7.0 Hz).

Step 3. 3-Acetylamino-2-benzoyl-1- (ethoxycarboniP-5-nitroindol) The title compound was prepared according to the procedure described in step 1 of example 2 (procedure A), starting from 3- amino-2-benzoyl-1- (ethoxycarbonyl) -5-nitroindole (step 2) tic: Rf = 0.2 (50% ethyl acetate in hexanes).

Step 4. 3-Acetylamino-2-benzoyl-5-nitroindol The title compound was prepared according to the procedure described in step 2 of example 2 (process A), starting from 3-acetylamino-2 -benzoyl-1- (ethoxycarbonyl) -5-nitroindole (step 3). p.f .: 210-212 ° C. ? -RMN (CDCI3 + CDOD3) d: 9.14 (1 H, d, J = 1.8 Hz), 8.19 (1 H, dd, j = 2.6, 9.2 Hz), 7.84 (1 H, d, J = 8.8 Hz) , 7.4-7.8 (5H, m), 2.20 (3H, s). IR (KBr) v: 1665, 1620, 1435, 1345, 1265, 1020, 915, 820 cm "1.

EXAMPLE 97 2- (3-Chlorobenzoyl) -3- (isovalerylamino) -5-n.troindole Step 1. 3-Amino-2- (3-chlorobenzoyl) -1- (ethoxycarboniP-5-nitroindol) The title compound was prepared according to the procedure described in step 2 of example 1, starting from 2- (ethoxycarbonyllamino) -5-nitrobenzonitrile (example 96, step 1) and 2-bromo-3'-chloroacetophenone. -RMN (CDCl 3) d: 9.19 (1 H, d, J = 2.2 Hz), 8.44 ( 1 H, dd, J = 2.2, 9.2 Hz), 8.21 (1 H, d, J = 9.2 Hz), 7.65-7.48 (6H, m), 3.81 (2H, q, J = 7.3 Hz), 0.86 (3H , t, J = 7.3 Hz).

Step 2. 3-amino-2- (3-chlorobenzoyl) -5-nitroindol The title compound was prepared according to the procedure described in step 3 of example 1, starting from 3-amino-2- ( 3-chlorobenzoyl) -1- (ethoxycarbonyl) -5-nitroindole (step 1). tic. Rf = 0.3 (33% ethyl acetate in hexanes).

Step 3. 2- (3-chlorobenzo-P-3- (isovalerylamino) -5-nitro-indole The title compound was prepared according to the procedure described in example 19, using 3-amino-2- (3- chlorobenzoyl) -5-nitroindole (stage 2) and sodium chloride, mp: 197-199 ° C, 1 H-NMR (CDCl 3) d: 9.91 (1 H, sa), 9.37 (1 H, d, J = 2.2 Hz), 8.73 (1 H, sa), 8.24 (1H, dd, J = 2.2, 9.2 Hz), 7.51-7.80 (4H, m). 7.38 (1 H, d, J = 9.2 Hz), 2.37 (2 H, s a), 2.24-2.29 (1 H, m), 1.07 (3 H, s), 1.05 (3 H, s).

EXAMPLE 98 3-Methoxyacetylamino-2- (3-methylbenzoyl) -5-nitroindole Step 1. 3-amino-1- (ethoxycarboniP-2- (3-methylbenzo-P-5-nitroindole) The title compound was prepared according to the procedure described in step 2 of example 1, starting from 2 - (ethoxycarbonylamino) -5-nitrobenzontrotyl (example 96, step 1) and 2-bromo-3'-methylacetophenone: Rf = 0.6 (33% ethyl acetate in hexanes).

Step 2. 1 - (EthoxycarboniP-3-methoxyacetylamine-2- (3-methylbenzoiP-5-nitroindol) The title compound was prepared according to the procedure described in step 1 of example 2 (procedure A ), from 3-amino-2- (3-chlorobenzoyl) -1- (ethoxycarbonyl) -5-nitroindol (step 1) and methoxyacetyl chloride. tlc: Rf = 0.6 (14% ethyl acetate in toluene) Step 3. 3-methoxyacetylamino-2- (3-methylbenzoiP-5-nitride) The title compound was prepared according to the procedure described in step 2 of example 2 (method A), starting from 1 - (Ethoxycarbonyl) -3-methoxyacetylamino-2- (3-methylbenzoyl) -5-nitroindole (step 2) .pf: 155-157 ° C.? -RMN (CDCl 3) d: 10.4 (1 H, sa, J = 1.8 Hz), 9.36 (1 H, d, J = 2.2 Hz), 8J7 (1 H, sa), 8.25 (1 H, dd, J = 2.2, 9.2Hz), 7.59-7.63 (2H, m). 7.46-7.48 (2H, m), 7.40 (1 H, d, J = 9.2 Hz), 4.09 (2H, s), 3.54 (3H, s), 2.47 (s, 3H).

EXAMPLE 99 3-Acetylamino-5-amino-2-benzoylindole Step 1. 3-Acetylamino-5-amino-2-benzoyl-1- (ethoxycarbonylPenol) 3-acetylamino-2-benzoyl-1- (ethoxycarbonyl) -5-nitroindole (Example 96, step 3, 200 mg, 0.51 mmol) in the presence of palladium on activated carbon (5%, 50 mg) in ethyl acetate (40 ml) at atmospheric pressure for 4 h. The catalyst was removed by filtration and the filtrate was concentrated to a produce the title compound.-NMR (CDCl 3) d: 8.99 (1 H, sa), 7.93 (1 H, d, J = 8.8 Hz), 7.76-7.69 (3H, m), 7.40-7.56 (3H, m ), 7.09 (1 H, sa), 4.77 (2H, sa), 3.91 (2H, q, J = 7.0 Hz), 1.64 (3H, s), 0.93 (3H, t, J = 7.0 Hz).

Step 2. 3-Acetylamino-5-amino-benzoylindole The title compound was prepared according to the procedure described in step 2 of example 2 (process A), starting from 3-acetylamino-5-a No-2-benzoyl-1- (ethoxycarbonyl) idol (step 1), in the form of a yellow solid, mp: 254-256 ° C.

-NRM (DMSO-de) d: 11.2 (1 H, s), 9.33 (1 H, s), 7.45-7.69 (5H, m), 7.16 (1 H, d, 8.4 Hz), 6.74 (1 H, dd, J = 2.2, 8.4 Hz), 7.16 (1 H, d, 8.4 Hz), 6J4 (1 H, dd, J = 2.2, 8.4 Hz), 6.58 (1 H, d, J = 2.2 Hz), 4.76 (2H, sa), 1.62 (3H, s).

EXAMPLE 100. 3-Acetylamino-2-benzoyl-5- (methanesulfonylamino) ndol To a solution of 3-acetylamino-5-amino-2-benzoyl-1-ethoxycarbonylindole (example 99, step 1: 100 mg, 0.27 mmol) in dichloromethane (5 ml) and pyridine (33 μl, 0.41 mmol), was added methanesulfonyl chloride (25 μl, 0.32 mmol) and the mixture was stirred for 1 h. The mixture was partitioned between 2N aqueous HCl (30 ml) and ethyl acetate (30 ml), the organic layer was separated and washed sequentially with brine (10 ml) and dried (MgSO 4). After removing the solvent, the residue was diluted with ethanol (10 ml) and water (5 ml) and potassium hydroxide (0.5 g) was added. The mixture was stirred for 4 h, poured into saturated aqueous ammonium chloride (30 ml) and extracted with ethyl acetate (50 ml x 2). The organic layer was washed with brine (50 ml), dried (MgSO) and the solvent was removed by evaporation. The residue was recrystallized from methanol / dichloromethane / hexane to give 66 mg of the title compound as a yellow solid, m.p .: 260-261 ° C. ? -NRM (DMSO-de) d: 11.7 (1 H, sa), 9.63 (1 H, s), 7.81-8.22 (2H, m), 7.40-7.64 (7H, m), 2.90 (3H, s) , 1.64 (3H, s). IR (KBr) v: 3640, 1665, 1610, 1545, 1325, 1270, 1140, 1010, 770 cm -1 EXAMPLE 101 3-Acetylamino-2-benzoyl-6-trifluoromethylindole Step 1. 2- (Ethoxycarbonylamino) -4-trifluoromethylbenzonitrile The title compound was prepared according to the procedure described in step 1 of example 1 (procedure B), from 2-amino-4-trifluoromethylbenzonitrile. (Y. Tomioka, K. Ohkubo and M. Yamazaki, Chem. Pharm. Bull., 1985, 33, 1360-1366). -NRM (CDCI3) d: 6.95-7.88 (3H, m), 4.65 (1 H, s a), 4.31 (2H, q, J = 7.3 Hz), 1. 28 (3H, t, J = 7.3 Hz).

Step 2. 3-amino-2-benzoyl-1 - (ethoxycarboniP-6-trifluoromethylindole) The title compound was prepared according to the procedure described in step 2 of example 1, starting with 2- (ethoxycarbonylamino) - 4-trifluoromethylbenzonitrile (step 1).? -NMR (CDCl 3) d: 8.54 (1 H, s), 7.77-7.72 (3H, m), 7.57-7.41 (4H, m), 5.79 (2H, sa), 3.77 (2H, q, J = 7.3 Hz), 0.86 (3H, t, J = 7.3 Hz).

Step 3-acetylamino-2-benzoyl-1- (ethoxycarboniD-6-trifluoromethylindole) The title compound was prepared according to the procedure described in step 1 of example 2 (method A), starting from 3-ami. no-2-benzoyl-1- (ethoxycarbonyl) -6-trifluoromethylnitride (step 2). tic: Rf = 0.6 (50% ethyl acetate in hexanes).

Step 4. 3-Acetylamino-2-benzoyl-6-trifluoromethylol The title compound was prepared in accordance with The procedure described in step 2 of example 2 (method A), starting from 3-acetylammonio-2-benzoyl-1- (ethoxycarbonyl) -6-trifluoromethylindole (step 3). p.f .: 177-179 ° C. ? -NRM (CDCI3) d: 9.88 (1 H, s), 9.45 (1 H, s), 7.99 (1 H, s), 7J2-7J0 (1 H, m), 7J0 (1 H, d, J = 8.8 Hz), 7.38-7.54 (4H, m), 7.08 (1 H, d, J = 8.8 Hz), 2.01 (3H, s).

EXAMPLE 102 3-Acetylamino-2-benzoyl-5-bromoindole • Step 1. 5-Bromo-2- (ethoxycarbonylamino) benzonitrile The title compound was prepared according to the procedure described in step 1 of example 1 (process B), starting from 2-amino-5 -benzonitrile (M. Hird, GW Gray and KJ Toyne, Mol.Cryst.Liq.Cryst, 1991, 206, 250-221). tic: Rf = OJ (33% ethyl acetate in hexanes) Step 2. 3-amino-2-benzoyl-5-bromo-1- (ethoxycarbonyl) indole The title compound was prepared according to the procedure described in step 2 of example 1, starting from Bromo-2- (ethoxycarbonylamino) benzonitrile (step 1). tic: Rf = 0.55 (33% ethyl acetate in hexanes) Step 3. 3-Acetylamino-2-benzoyl-5-bromo-1- (ethoxycarbonyl) d-ol The title compound was prepared according to the procedure described in step 1 of example 2 (method A) a from 3-amino-2-benzoyl-5-bromo-1- (ethoxycarbonyl) idol (step 2). tic: Rf = 0.3 (33% ethyl acetate in hexanes).

Step 4. 3-Acetylamino-2-benzoyl-5-bromoindole The title compound was prepared according to the procedure described in step 2 of example 2 (procedure A), starting from 3-acetylamine-2-benzo L-5-bromo-1- (ethoxycarbonyl) indole (step 3). p.f .: 192- 194 ° C. 1 H-NMR (DMSO-de) d: 11.8 (1 H, s a), 9.65 (1 H, s), 7.35-7J9 (8H, m), 1.69 (3H, s).

EXEMPL0103 3-Acetylamino-2-benzoyl-5-chloroindole Step 1. 3-Amino-2-benzoyl-5-chloro-1- (ethoxycarbonolindol) The title compound was prepared according to the procedure described in step 2 of example 1, starting with 5-chloro-2- (ethoxycarbonylamino) benzonitrile (KO Geolotte et al., J. Heterocyclic Chem., 1990, 27, 1549) and 2-bromoacetophenone. -RMN (CDCI3) d: 8.15 (1 H, d, J = 9 Hz), 7.74 (2 H, dd, J = 8.2 Hz), 7. 58 (1 H, d, J = 2 Hz), 7.52-7.43 (4H, m), 5.70 (2H, s a), 3.73 (2H, q, J = 7 Hz), 0. 84 (3H, t, J = 7Hz).

Step 2. 3-Acetylamlan-2-benzoyl-5-chloro-1- (ethoxycarboniPindol) The title compound was prepared according to the procedure described in step 1 of example 2 (procedure A), starting from 3-amino-2-benzoyl-5-chloro-1- (ethoxycarbonyl) indole (step 1) and acetyl chloride.? -RMN (CDCl 3) d: 8.84 (1 H, sa), 8.14 (1 H, d, J = 9 Hz), 7.96 (1 H, s) 7.76 (2H, d, J = 8 Hz), 7.57-7.44 (4H, m), 3.92 (2H, q, J = 7 Hz), 2.23 (3H, s), 0.93 (3H, t, J = 7Hz).

Step 3. 3-Acetylamino-2-benzoyl-5-chloro-inol The title compound was prepared according to the procedure described in step 2 of example 2 (procedure A), starting from 3-acetylamino -2-benzoyl-5-chloro-1- (ethoxycarbonyl) indole (step 2). p.f .: 200-201 ° C. (ethyl acetate) - NMR (CDCl 3) d: 9.70 (1 H, sa), 8.28 (1 H, sa), 8.25 (1 H, s), 7.80 (2H, dd, J = 8, 1.5 Hz) , 7.65-7.56 (3H, m) 7.33 (1 H, dd, J = 8, 1.5 Hz), 7.23 (1 H, d, J = 8 Hz), 2.24 (3H, s). IR (KBr) v: 3250, 1670, 1535, 1270, 800, 730 cm "1.

EXAMPLE 104 5-Chloro-2- (3-chlorobenzoyl) -3- (propionylamino) indole Stage 1. 3-Amino-5-chloro-2- (3-chlorobenzo-P-1- (ethoxycarboniPndol) The title compound was prepared according to the procedure described in step 2 of Example 1, starting from 5-chloro-2- (ethoxycarbonylamino) benzonitrile (K.O. Geolotte et al., J. Heterocyclic Chem., 1990, 27, 1549) and 2-bromo-3'-chloroacetophenone (M. Kihara et al., Tetrahedron, 1992, 48, 67-68). ? -RMN (CDCI3) d: 8.15 (1 H, dd, J = 10, 1 Hz), 7.75 (1 H, t, J = 1.5 Hz), 7.60-7.43 (4H, m), 7.36 (1 H, t, J = 8 Hz), 5.78 (2H, sa), 3.83 (2H, q, J = 7 Hz), 0.92 (3H, t, J = 7 Hz).

Step 2. 5-Chloro-2- (3-chlorobenzolP-3- (propionylamino) indole The title compound was prepared according to the procedure described in Example 2 (procedure A), starting from 3-amino- 5-chloro-2- (3-chlorobenzoyl) -1- (ethoxycarbonyl) indole (step 1) and propionyl chloride mp: 206.5-207.5 ° C (ethyl acetate).? -RMN (CDCl3) d: 9.78 ( 1 H, sa), 8.31 (1H, s), 8.28 (1 H, sa), 7J8 (1 H, s), 7J0-7.59 (2H, m), 7.51 (1 H, t, J = 8 Hz) , 7.34 (1 H, dd, J = 8, 1.5 Hz), 7.25 (1 H, d, J = 8 Hz), 2.51 (2 H, q, J = 7 Hz), 1.30 (3 H, t, J = 7 Hz). IR (KBr) v: 3300, 1680, 1580, 1540, 700 cm "1.

EXAMPLE 105 3-Acetylamino-2-benzoylindole Step 1. 3-acetylamino-2-benzoyl-1- (ethoxycarboniPindol) The title compound was prepared according to the procedure described in step 1 of example 2, (process A) from 3-amino-2-benzoyl- 1- (ethoxycarbonyl) indole (EE Garcia, LE Benjamin and R. lanFryer, J. Heterocyclic Chem., 1973, 10, 51-53) and acetyl chloride. 112-113 ° C (ethyl acetate / isopropyl ether). ? -RMN (CDCI3) d: 9.05 (1 H, sa), 8.21 (1 H, d, J = 8 Hz), 7.98 (1 H, d, J = 8 Hz), 7.79 (2 H, d, J = 8 Hz), 7.60-7.43 (4H, m), 7.34 (1 H, t, J = 8 Hz), 3.90 (2H, q, J = 7 Hz), 2.24 (3H, s), 0.94 (3H, t, J = 7 Hz).

Stage 2. 3-acetylamino-2-benzoyl? The title compound was prepared according to the procedure described in step 2 of example 2 (method A), starting from 3-acetylamino-2-benzoyl-1- (ethoxycarbonyl) indole (step 1). 1 H-NMR (CDCl 3) d: 9.78 (1 H, sa), 8.24 (1 H, d, J = 8 Hz), 8.22 (1 H, sa), 7.82 (2 H, d, J = 8 Hz), 7.64 - 7.52 (3H, m), 7.42-7.25 (2H, m), 7.16 (1 H, t, J = 8 Hz), 2.26 (3H, s). IR (KBr) v: 3360, 1670, 1620, 1540, 730 cm "1.

EXAMPLE 106 • 10 3-Acetylamino-2-benzoyl-4-chloroindole Step 1. 6-Chloro-2- (ethoxycarbonylamino) benzonitrile The title compound was prepared according to the procedure described in step 1 of example 1, (process B) from of 2-amino-6-chlorobenzonitrile. mp .: 144.5-145.1 ° C (ethyl acetate / hexane). ? -NRM (CDCI3) d: 8.21 (1 H, d, J = 8 Hz), 7.49 (1 H, t, J = 8 Hz), 7.16 (1 H, d, J = 8 • Hz), 7.17 (1 H, s a), 4.27 (2 H, q, J = 7 Hz), 1.35 (3 H, t, J = 7 Hz).

Step 2. 3-Amino-2-benzoyl-4-chloro-1- (ethoxycarbonyl) indole The title compound was prepared according to the procedure described in step 2 of example 1, starting from 6-chloro -2- (ethoxycarbonylamino) benzonitrile (step 1) and 2-bromoacetophenone. mp .: 118-119 ° C (isopropyl ether).

? -RMN (CDCI3) d: 8.15 (1 H, d, J = 8 Hz), 7J3 (2H, dd, J = 7.2 Hz), 7.46-7.40 (4H, m), 7.24 (1 H, d, J = 7 Hz), 6.54 (2H, sa), 3.69 (2H, q, J = 7 Hz), 0.83 (3H, t, J = 7 Hz).

Step 3. 3-Acetylamino-2-benzoyl-4-chloro-1- (ethoxycarbonolindol) The title compound was prepared according to the procedure described in step 1 of example 2 (method A), a from 3-amino-2-benzoyl-4-chloro-1- (ethoxycarbonyl) indole (step 2). 1 H-NMR (CDCl 3) d: 8.16 (1 H, d, J = 8 Hz), 7.85 (2H , d, J = 7 Hz), 7.63-7.25 (6H, m), 4.08 (2H, q, • 10 j = 7 Hz), 2.08 (3H, s), 0.99 (3H, t, J = 7 Hz).

Step 4. 3-Acetylamino-2-benzoyl-4-chloro-inol The title compound was prepared according to the procedure described in step 2 of example 2 (method A), starting from 3-acetylamino-2- Benzoyl-4-chloro-1- (ethoxycarbonyl) indole (step 3). mp .: 221-222 ° C (ethyl acetate / hexane). -NRM (CDCI3) d: 9.12 (1 H, s a), 7.82 (2H, • d, J = 7 Hz), 7.60-7.20 (6H, m), 7.12 (1 H, d, J = 7 Hz), 1.79 (3H, s). IR (KBr) v: 3400, 3150, 1670, 1630, 1507, 1270, 780, 730 cm "1.

EXAMPLE 107 3-Acetylamino-2-benzoyl-4-fluoroindole Step 1. 2- (Ethoxycarbonylamino) -6-fluorobenzonitrile The title compound was prepared according to the procedure described in step 1 of example 1, (process B) from 2-amino-6-fluorobenzonitri the. tic: Rf = 0.75 (33% ethyl acetate in hexanes).

Step 2. 3-amino-2-benzoyl-1- (ethoxycarboniP-4-fluoroindole) The title compound was prepared according to the procedure described in step 2 of example 1, starting from 2- ( ethoxycarbonylamino) -6-fluorobenzonitrile (stage 1) and 2-bromoacetophenone: Rf = 0.3 (33% ethyl acetate in hexanes) 15 Step 3. 3-Acetylamino-2-benzoyl-1 - (ethoxycarboniP-4-) fluoroindole The title compound was prepared according to the procedure described in step 1 of example 2, (method A) from 3-amino-2-benzoyl-1- (ethoxycarbonyl) -4-fluoroindole (step 2). -RMN 20 (CDCI3) d: 8.70 (1 H, s), 7.72 (2H, d, J = 8.4 Hz), 7.55-7.38 (5H, m), 7.20 (1 H, dd, J = 8.1, 13.6 Hz ), 6.78 (1 H, dd, J = 8.4, 9.9 Hz), 4.05 (2H, q, J = 7.3 Hz), 2.12 (3H, s), 0.99 (3H, t, J = 7.3 Hz).

Step 4. 3-acetylamino-2-benzoyl-4-fluoroindole The title compound was prepared according to the procedure described in step 2 of example 2, (process A) starting from 3-acetylamino-2-benzoyl- 1- (ethoxycarbonyl) -4-fluoroindole (step 3). p.f.:131- 133 ° C. ? -NRM (CDCI3) d: 8.92 (1 H, sa), 7.81 (1 H, d, J = 8.4 Hz), 7.80 (1 H, sa), 7.61-7.46 (3H, m), 7.29-7.15 ( 2H, m), 6.80 (1 H, dd, J = 7J, 10.7 Hz), 1.91 (3H, s).

EXAMPLE 108 3-Acetylamino-2-benzoyl-6-fluoroindole Step 1. 2- (Ethoxycarbonylamino) -4-fluorobenzonitrile The title compound was prepared according to the procedure described in step 1 of example 1, (process B) from 2-amino-4-fluorobenzonitrile. tic: Rf = 0.7 (25% ethyl acetate in hexanes).

Step 2. 3-amino-2-benzoyl-1- (ethoxycarbonyl) -6-fluoroindole The title compound was prepared according to the procedure described in step 2 of example 1, starting from 2 - (ethoxycarbonylamino) -4-fluorobenzonitrile (stage 1) and 2-bromoacetophenone, 1 H-NMR (CDCl 3) d: 7.94 (1 H, dd, J = 2.7, 10.3 Hz), 7.76-7.72 (2H, m) , 7.57 (1 H, dd, J = 5.5, 8.8 Hz), 7.51-7.39 (3H, m), 7.06 (1 H, ddd, J = 2.7, 8.8, 10.3 Hz), 5.87 (2H, sa), 3.74 (2H, q, J = 7.3 Hz), 0.84 (3H, t, J = 7.3 Hz).

Step 3. 3-Acetylamino-2-benzoyl-1 - (ethoxycarbonyl) -6-fluoro-inol The title compound was prepared according to the procedure described in step 1 of example 2, (process A) from 3 -amino-2-benzoyl-1- (ethoxycarbonyl) -6-fluoroindole (step 2). tic: Rf = 0.2 (33% ethyl acetate in hexanes).

Step 4. 3-acetylamino-2-benzoyl-6-fluoro-inol The title compound was prepared according to the procedure described in step 2 of example 2 (process A), starting from 3-acetylamino-2 -benzoyl-1- (ethoxycarbonyl) -6-fluoroindole (step 3). p.f .: 144-145 ° C. -RMN (CDCI3) d: 9.96 (1 H, sa), 8.44 (1 H, sa), 8.25 (1 H, dd, J = 5.5, 8.8 Hz), 7.80-7.71 (2H, m), 7.65-7.51 (3H, m), 6.94-6.85 (2H, m), 2.22 (3H, s).

EXAMPLE 109 3-Acetylamino-2-benzoyl-6-methylindole Step 1. 2- (Ethoxycarbonylamino) -4-methylbenzonitrile The title compound was prepared according to the procedure described in step 1 of example 1, (process B) from 2-amino -4-methylbenzon? Trílo. ? -RMN (CDCI3) d: 8.06 (1 H, s), 7.43 (1 H, d, J = 7.7 Hz), 7.10 (1 H, sa), 6.92 (1 H, d, J = 7.7 Hz), 4.25 ( 2H, q, J = 7.3 Hz), 2.40 (3H, s), 1.35 (3H, t, J = 7.3 Hz).

Step 2. 3-amino-2-benzoyl-1- (ethoxycarbonyl-P-6-methylindol) The title compound was prepared according to the procedure described in step 2 of example 1, starting with 2- (ethoxycarbonylamino) - 4-methylbenzonitrile (step 1) and 2-bromoacetophenone: tic: Rf = 0.6 (25% ethyl acetate in hexanes).

• Step 3. 3-Acetylamino-2-benzoyl-1- (ethoxycarboniP-6-methylindole) The title compound was prepared according to the procedure described in step 1 of example 2, (process A) from 3-amino-2-benzoyl-1- (ethoxycarbonyl) -6-methylindol (step 2). 1 H-NMR (CDCl 3) d: 9.29 (1 H, sa), 7.78-7.38 (5H, m), 7.84 ( 1 H, s), 7.77 (1 H, d, J = 8.4 Hz), 7.02 (1 H, d, J = 8.4Hz), 3.92 (2H, q, J = 7.3 Hz), 2.46 (3H, s), 2.18 (3H, s), 0.94 (3H, t, J = 7.3 Hz) .

Step 4. 3-Acetylamino-2-benzoyl-6-methylindole The title compound was prepared in accordance with The procedure described in step 2 of example 2 (method A), starting from 3-acetylamino-2-benzoyl-1- (ethoxycarbonyl) -6-methylindole (step 3). p.f .: 136-138 ° C. -NRM (CDCI3) d: 9.92 (1 H, sa), 8.16-8.13 (2H, sa), 7.81-7.78 (2H, m), 7.52-7.65 (3H, m), 7.05 (1H, sa), 6.97 (1 H, dd, J = 1.1, 8.4 Hz), 2.44 (3H, s), 2.23 (3H, s).

EXAMPLE 110 3-Acetylamino-2-benzoyl-6-cyanoindole Step 1. 4-Cyano-2- (ethoxycarbonylamino) benzonitrile The title compound was prepared according to the procedure described in step 1 of example 1 (method B), starting from 2-amino-4-cyanobenzonitrile. tic: Rf = 0.6 (25% ethyl acetate in hexanes).

Step 2. 3-amino-2-benzoyl-6-cyano-1- (ethoxycarbonyl) d-ol The title compound was prepared according to the procedure described in step 2 of example 1, starting from 4 -cyano-2- (ethoxycarbonylamino) benzonitrile (step 1) and 2-bromoacetophenone. tic: Rf = 0.2 (25% ethyl acetate in hexanes).

Step 3. 3-Acetylamino-2-benzoyl-6-cyano-1- (ethoxycarbon) -Pndol The title compound was prepared according to the procedure described in step 1 of example 2 (procedure A) , from 3-amino-2-benzoyl-6-cyano-1 - (ethoxycarbonyl) indole (step 2). tic: Rf = 0.1 (33% ethyl acetate in hexanes).

Step 4. 3-acetylamino-2-benzoyl! -6-cyano-inol The title compound was prepared according to the procedure described in step 2 of example 2 (procedure A), starting from • of 3-acetylamino-2-benzoyl-6-cyano-1- (ethoxycarbonyl) -indole (step 3). p.f .: 224- 246 ° C. ? -NRM (DMSO-d6) d: 12.33 (1 H, sa), 9.80 (1 H, s), 7.90 (1 H, d, J = 1.5 Hz), 7.79-7.49 (6H, m), 7.42 ( 1 H, dd, J = 1.5, 8.4 Hz), 1.68 (3H, s).

EXAMPLE 111 3-Acetylamino-5-bromo-6-chloro-2- (6-methy1pyridine-2-carbonyl) indole • 10 Stage 1. 3-amino-6-chloro-1- (ethoxycarbon-P-2- (6-methy1pyridine-2-carboniPindol and 3-amine-5-bromo-6-chloro-1) - (EthoxycarboniD-2- (6-methylpyridine-2-carboniPindol) The title compound was prepared in accordance with The procedure described in step 2 of Example 1, starting with 4-chloro-2- (ethoxycarbonylamino) benzonitrile and 2-bromoacetyl-6-methylpyridine bromide.

• (H. Erlenmeyer, J, Jenni and B. Prijs, J. Med. Pharm. Chem., 1961, 3, 561-566). 3-amino-5-bromo-6-chloro-1- (ethoxycarbonyl) -2- (6-methy1pyridine-2-carbonyl) indol (3%):? -RMN (CDCl3) d: 8.36 (1 H, s), 7.90 (1 H, d, J = 7.7 Hz), 7.86 (1 H, s), 7.77 (1 H, t, J = 7.7 Hz), 7.26 (1 H, d, J = 7.3 Hz), 5.90 (2H, sa), 3.74 (2H, q, J = 7.2 Hz), 2.56 (3H, s), 0.84 (3H, t, J = 7.2 Hz). 3-amino-6-chloro-1- (ethoxycarbonyl) -2- (6-methylpyridine-2-carbonyl) indole (46%): 1 H-NMR (CDCl 3) d: 8.23 (1 H, d, J = 1.8 Hz), 7.90 (1 H, d, J = 7.7 Hz), 7.76 (1 H, t, J = 7.7 Hz), 7.52 (1 H, d, J = 8.1 Hz), 7.26-7.22 (2H, m), 6.00 (2H, sa), 3J3 (2H, q, J = 7.0 Hz), 2.56 (3H, s), 0.85 (3H, t, J = 7.0 Hz).

Step 2. 3-Acetylamino-5-bromo-6-chloro-1- (ethoxycarboniP-2- (6-methylpyridine-2-carbon) -Pindol The title compound was prepared according to the procedure described in step 1 of Example 2 (procedure A), starting from 3-amino-5-bromo-6-chloro-1- (ethoxycarbonyl) -2- (6-methylpyridine-2-carbonyl) indole (step 1) 10 tic: Rf = 0.1 (33% ethyl acetate in hexanes) Step 3. 3-Acetylamino-5-bromo-6-chloro-2- (6-methylpyridine-2-carboniPindol) The title compound was prepared according to the procedure described in step 2 of example 2 ( procedure A), from 3-acetylamino-5-bromo-6-chloro-1- (ethoxycarbonyl) -2- (6-methylpyridine-2-carbonyl) indole (step 2) .pdf: 234-236 ° C (dichloromethane / methanol) -NMR (DMSO-de) d: 12.01 (1 H, sa), 10.26 (1 H, sa), 8.21 (1 H, s), 7.98 (1 H, t, J = 7J Hz), 7.86 (1 H, d, J = 7 J Hz), 7.85 (1 H, s), 7.57 (1 H, d, J = 7 J Hz), 2.66 (3 H, s), 20 1.99 (3 H, s) .

EXAMPLE 112 3-Amino-6-chloro-2- (6-methylpyridine-2-carbonyl) indole The title compound was prepared according to the procedure described in step 2 of Example 1, starting from 3-amino-6-chloro-1- (ethoxycarbonyl) -2- (6-methylpyridine-2-carbonyl ) Ndol (example 111, stage 1). mp .: 210-211 ° C (ethyl acetate). 1 H-NMR (DMSO-d 6) d: 10.85 (1 H, sa), 7.97-7.90 (3H, m), 7.59 (1H, sa), 7.50 (1H, t, J = 4.4 Hz), 7.34 (2H, sa), 6.93 (1H, dd, J = 1.8, 8.4 Hz), • 10 2.73 (3H, s).

EXAMPLE 113 3-Acetylamino-6-chloro- (6-methylpyridine-2-carbonyl) indole The title compound was prepared according to the procedure described in example 19, using 3-acetylamino-6-chloro-2- (6-methylpyridine-2-carbonyl) indole (example 112). mp .: 195-196 ° C (ethyl acetate). ? -NRM (DMSO-de) d: 11.88 (1 H, s a), 10.24 (1 H, s a), 7.97 (1 H, t, J = 7.7 Hz), 7.85 (1 H, d, J = 7.7 Hz), 7.81 (1 H, d, J = 8.8 Hz), 7.63 (1 H, d, J = 1.8 Hz), 7.56 ( 1H, d, J = 7.7 Hz), 7.08 (1H, dd, J = 1.8, 8.8 Hz), 2.67 (3H, s), 1.97 (3H, s).

EXAMPLE 114 2-Benzoyl-6-chloro-3-r (2-tetrahydrofurylcarboxamidolindole) A mixture of 3-amino-3-benzoyl-6-chloroindole (example 1. 380 mg, 1.4 mmol), tetrahydro-2-furancarboxylic acid (490 mg, 4.2 mmol) and 1-ethoxycarbonyl-2-ethoxy-1, 2 Dihydroquinoline (EEDQ, 1.04 g, 4.2 mmol) in THF (20 ml) was heated to reflux and stirred for 20 hours. The mixture was cooled, poured into 2N aqueous HCl (30 ml) and extracted with diethyl ether (50 ml). The organic extract was washed with saturated sodium bicarbonate (30 ml), dried (MgSO 4) and the solvent was evaporated. The residue was purified by flash chromatography eluting with ethyl acetate / hexane (1: 1) to yield 500 mg (97%) of the title compound as a light brown liquid. ? -NMR (CDCI3) d: 10.56 (1 H, s a), 8.62 (1 H, s a), 8.23 (1 H, d, J = 1.8 Hz), 7.08 (1 H, dd, J = 8.8, 1.8 Hz), 4.55-4.38 (1 H, m), 4.25-3.85 (3H, m), 2.40-1.85 (3H, m).

EXAMPLE 115 2-Benzoyl-6-chloro-3-r (2-methoxypropionyl) amino1indole The title compound was prepared according to the procedure described in Example 114, using 3-amino-2-benzoyl-6-chloroindole (example 1) and 2-methoxypropionic acid. mp .: 169-171 ° C (ethyl acetate / hexane). ? -NRM (CDCI3) d: 10.43 (1 H, sa), 8.49 (1 H, sa), 8.20 (1 H, d, J = 8.8 Hz), 7.83-7.76 (2H, m), 7.65-7.50 ( 3H, m), 7.30 (1 H, d, J = 1.8 Hz), 7.09 (1 H, dd, J = 1.8, 8.8 Hz), 3.88 (1 H, q, J = 7.0 Hz), 3.48 (3H, s), 1.45 (3H, d, J = 7.0 Hz).

EXAMPLE 116 2-Benzoyl-6-chloro-3- (3,3,3-trifluoropropionylamino) indole The title compound was prepared according to the procedure described in example 114, using 3-amino-2-benzoyl-6-chloroindole (example 1) and 3,3,3-trifluoroproponic acid. p.f .: 201-204 ° C (ethyl acetate / hexane). ? -NRM (CDCI3) d: 10.35 (1 H, sa), 8.34 (1 H, sa), 8.22 (1 H, d, J = 8.8 Hz), 7.88-7.75 (5H, m), 7.31 (1 H , d, J = 1.8 Hz), 7.13 (1 H, dd, J = 8.8, 1.8 Hz), 3.46-3.30 (2H, m).

EXAMPLE 117 2-Benzoyl-6-chloro-3- (cyclopropanoacetylamino) indole The title compound was prepared according to the procedure described in Example 114, employing 3-amino-2-benzoyl-6-chloroindole (Example 1) and cyclopropylacetic acid. p.f .: 72-75 ° C.

-NRM (CDCI3) d: 10.33 (1 H, sa), 8.34 (1 H, sa), 8.27 (1 H, d, J = 9.2 Hz), 7.83-7J5 (2H, m), 7.67 (3H, m ), 7.27 (1H, d, j = 1.8 Hz), 7.09 (1 H, dd, J = 9.2, 1.8 Hz), 2.38 (2H, d, J = 7.3 Hz), 1.21-1.05 (1 H, m) , 0.80-0.70 (2H, m), 0.38-0.27 (2H, m).

EXAMPLE 118 2-Benzoyl-6-chloro-3-r (3-hydroxy-3-methyl) -butyrylamino-indole The title compound was prepared according to the procedure described in Example 114, employing 3-amino-2-benzoyl-6-chloroindole (Example 1) and 3-hydroxyisovaleric acid. p.f .: 179-182 ° C. 1 H-NMR (CDCl 3) d: 10.07 (1 H, sa), 8.37 (1 H, sa), 8.16 (1 H, d, J = 9.2 Hz), 7.86-7.77 (2H, m), 7.70-7.53 ( 3H, m), 7.30 (1 H, d, J = 1.8 Hz), 7.12 (1 H, dd, J = 9.2, 1.8 Hz), 3.98 (1 H, sa), 2.62 (2H, s), 1.36 ( 6H, s).

EXAMPLE 119 2-Benzoyl-6-chloro-3- (methylthioacetylamino) indole The title compound was prepared according to the procedure described in Example 114, employing 3-amino-2-benzoyl-6-chloroindole (Example 1) and methylthioacetic acid. p.f .: 63-70 ° C. 1 H-NMR (CDCl 3) d: . 78 (1 H, sa), 8.42 (1 H, sa), 8.16 (1 H, d, J = 9.2 Hz), 7.86-7.79 (2 H, m), 7.68- 7.53 (3 H, m), 7.31 (1 H , d, J = 1.8 Hz), 7.12 (1 H, dd, J = 9.2, 1.8 Hz), 3.39 (2H, s), «*» * 2.23 (3H, s).

EXAMPLE 120 AND EXAMPLE 121 2-Benzoyl-6-chloro-3- (methylsulfinylacetylamino) indole (Example 120) and 2-Benzoyl-6-chloro-3- (methylsulphonylacetylamino) indole (Example 121) A mixture of 2-benzoyl-6-chloro-3- (methylthioacetylamino) idol (example 119, 0.87 g, 2.4 mmol) in methanol (20 ml) and oxone (2.9 g, 4.8 mmol) in water (10 ml) ), stirred for 10 minutes, poured into aqueous sodium thiosulfate (50 ml) and extracted with diethylmethane (30 ml x 2). The combined organic extract was dried (MgSO) and the solvent was removed by evaporation. The residue was purified by flash chromatography eluting with ethyl acetate / hexane (1: 1) to yield 280 mg (31%) of the sulfoxide (less polar) and 130 mg (14%) of sulfone (more polar), respectively. Recrystallization from ethyl acetate and n-hexane afforded 220 mg (24%) of sulfoxide as yellow solids and recrystallization from ethyl acetate afforded 90 mg (10%) of the sulfone as yellow solids. 2-Benzoyl-6-chloro-3- (methylsulfinyl-lathylamino) ddol (Example 120) mp: 191-192 ° C (ethyl acetate / hexane, yellow solids) - NMR (CDCl 3) d: 10.29 ( 1 H, sa), 10.06 (1 H, sa), 7.94 (1 H, d, J = 8.8 Hz), 7.88-7.82 (2H, m), 7.65-7.49 (3H, m), 7.43 (1 H, d, J = 1.8 Hz), 7.09 y¡ > (1 H, dd, J = 8.8, 1.8 Hz), 3J3 (1 H, d, J = 13.6 Hz), 3.57 (1 H, d, J = 13.6 Hz), 2J5 (3H, s) and 2-Benzoyl-6-chloro-3- (methylsulfonylacetylamino) ethylene (Example 121) mp: 217-220 ° C (ethyl acetate, yellow solids) -NMR (CDCl 3) d: 10.27 (1 H, sa), 8.50 (1 H, sa), 8.06 (1 H, d, j = 8.8 Hz), 7.88-7J9 (2 H, m), 7 J2-7.52 (3 H, m), 7.34 (1 H, d, J = 1.8 Hz) , 7.13 (1 H, dd, J = 8.8, 1.8 Hz), 4.10 (2H, s), 3.19 (3H, s).

EXAMPLE 122 2-Benzoyl-6-chloro-3-f (n, n-dimethylaminoacetyl) amino1indole Step 1. 2-Benzoyl-6-chloro-3-chloroacetylamino-1- (ethoxycarboniPindol) The title compound was prepared according to the procedure described in step 1 of example 2 (procedure A), starting from 3-amino- 2-benzoyl-6-chloro-1- (ethoxycarbonyl) indole (example 1, step 2) and chloroacetyl chloride-NMR (CDCl 3) d: 9.86 (1 H, sa), 8.27 (1 H, d, J = 1.8 Hz), 7.92 (1 H, d, J = 8.8 Hz), 7.81-7.72 (2 H, m), 7.62-7.42 (3 H, m), 7.33 (1 H, dd, J = 1.8, 8. 8 Hz), 4.20 (2H, s), 3.92 (2H, q, J = 7.0 Hz), 0.94 (3H, t, J = 7.0 Hz).

H3 Step 2. 2-Benzoyl-6-chloro-3 - [(N, N-dimethylaminoacetiPaminolindol A mixture of 2-benzoyl-6-chloro-3- (chloroacetylamine) -1- (ethoxycarbonyl) indole (step 1, 890 mg, 2.12 mg) and dimethylamine hydrochloride (520 mg, 6.36 mmol) in DMF (30 ml) was stirred for 2 h, water (80 ml) was added and the mixture was extracted with a mixture of ethyl acetate-toluene (2: 1 v / v, 30 ml x 2) The combined organic extracts were washed consecutively with water (50 ml) and brine (50 ml), dried (MgSO 4) and evaporated The residue was treated with a 1 N aqueous solution of KOH and EtOH (40 ml) for 1 h, the volatiles were removed by evaporation and the residue was extracted with ethyl acetate (30 ml x 2) The combined organic extracts were dried (MgSO) and evaporated. was recrystallized from ethyl acetate / hexane to give 350 mg (47%) of the title compound as a yellow solid, mp 175-176 ° C. NMR (CDCl 3) d: 10.60 (1 H, sa), 8.83 (1 H, sa), 8.08 (1 H, d, J = 8.8 Hz), 7.88-7J0 (2H, m), 7.68-7.42 (3H, m), 7.29 (1 H, dd, J = 1.8, Hz), 7.07 (1 H, d, J = 1.8, 8.8 Hz), 3.04 (2H, s), 2.33 (6H, s). IR (KBr) v: 1660, 1620, 1570, 1540, 1250, 1240, 1050, 920 cm "1.

EXAMPLE 123 3-Acetylamino-2-benzoyl-5,6-dimethoxyindole Step 1. 4,5-Dimethoxy-2- (ethoxycarbonylamino) benzonitrile The title compound was prepared according to the procedure described in step 1 of example 1 (procedure B), starting from -? 3? _ «R.» _-- BSi of 2-amino-4,5-dimethoxybenzonitrile tic: Rf = OJ (33% ethyl acetate in hexanes).

Step 2. 3-Amino-2-benzoyl-5,6-dimethoxy-1- (ethoxycarbonylPenol) The title compound was prepared according to the procedure described in step 2 of Example 1, starting from 4,5-dimethoxy-2- (ethoxycarbonylamino) benzonitrile (step 1) tic: Rf = 0.2 (33% ethyl acetate in hexanes).

Step 3-Acetylamino-2-benzoyl-4,5-d-methoxy-1- (ethoxycarboniPindol) The title compound was prepared according to the procedure described in step 1 of example 2, (process A), a from 3-amino-2-benzoyl-5,6-dimethoxy-1- (ethoxycarbonyl) indole (step 2). tic: Rf = 0.6 (50% ethyl acetate in hexanes). fl) Step 4. 3-Acetylamino-2-benzoyl-4,5-dimethoxyindole The title compound was prepared according to the procedure described in step 2 of example 2, (method A), starting from of 3-acetylamino-2-benzoyl-4,5-dimethoxy-1- (ethoxycarbonyl) idol (step 3). mp: 118-120 ° C? -RMN (CDCI3) d: 10.2 (1 H, sa), 8.44 (1 H, sa), 7J4-7J8 (3H, m), 7.47-7.57 (3H, m), 6.64 (1 H, s), 3.91 (3H, s), 3.84 (3H, s), 2.23 (3H, s). IR (KBr) v: 1665, 1540, 1495, 1265, 1220, 11120, 1015, 835 cm. " EXAMPLE 124 3-Acetylamino-6-chloro-2-r (1-methylimidazol-2-iPcarbonillindole) Step 1. Methyl 3-amino-6-chloro-1- (ethoxycarboniP-2-carboxylate) The title compound was prepared according to the procedure described in step 2 of example 1, starting from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 2) and methyl bromoacetate-NMR (CDCl 3) d: 8.08 (1 H, d, J = 1.8 Hz), 7.42 (1 H, d, J = 8.8 Hz), 7.22 (1 H, dd, J = 8.8, 1.8 Hz), 5.17 (2H, sa), 4.40 (2H, q, J = 7.3 Hz), 3.88 (3H, s), • 10 1.40 (3H, t, J = 7.3 Hz). t -? Step 2. 3-Acetylamino-6-chloro-1- (ethoxycarboniPindol-2-methyl carboxylate) The title compound was prepared in accordance with The procedure described in step 1 of example 2, (method A), from methyl 3-amino-6-chloro-1- (ethoxycarbonyl) indole-2-carboxylate (step 1). 1 H-NMR (CDCl 3) d: 8.80 (1 H, sa), 8.05 (1 H, d, J = 1.8 Hz), 7.92 (1 H, d, J = 8.4 Hz), 7.23 (1 H, dd, J = 8.8, 1.8 Hz), 4.44 (2H, q, J = 7.3 Hz), 3.92 (3H, s), 2.27 (3H, s), 1.43 (3H, t, J = 7.3 Hz). Step 3. 3-Acetylamino-6-chloroindole-2-carboxylic acid 3-Acetylamino-6-chloro-1- (ethoxycarbonyl) -indole-2-carboxylic acid methyl ester was dissolved (step 2, 1.48 g, 4.37 mmoles) in ethanol (20 ml) and 1 N aqueous KOH (10 ml), at reflux, for 1 h, the mixture was cooled and concentrated, the residue was diluted with 1 N aqueous HCl (20 ml) and extracted with ethyl acetate (30 ml x 2) .The organic extract was dried (MgSO 4) and evaporated to yield 0.95 g (86%) of the title compound as a white solid.-NMR (CDCl 3) d: 11.69 (1 H, s), 9.58 (1 H, s), 7.63 (1 H, dd, J = 8.8, 1.5 Hz), 7.38 (1 H, d, J = 1.5 Hz), 7.03 (1 H, d, J = 8.4 Hz), 2.11 (3H, s).

Step 3-Acetylamino-6-chloro-2-r (N-methoxy-N-methylamino) carbonnadol To a mixture of (3-acetylamino-6-chloroindole) -2-carboxylic acid (step 3, 280 mg, 1.11 mmol), diphenyl phosphoryl azide (365 mg, 1.33 mmol) and N, O-dimethylhydroxylamine hydrochloride (162 mg, 1.66 mmol) in dimethylformamide (5 ml), triethylamine was added. (0.58 ml, 4.16 mmol). After stirring for 1 h, the mixture was diluted in water (10 ml) and extracted with diethyl ether (30 ml x 2). The combined organic extracts were washed consecutively with water (20 ml x 2), saturated sodium bicarbonate (20 ml), brine (20 ml) and then dried (MgSO). Removal of the solvent gave the title compound as a brown solid (ca. 20%) which was used in the next step without further purification. -NRM (CDCI3) d: 10.00 (1 H, sa), 8.12 (1 H, m), 7.42-7.12 (3H, m), 3.80 (3H, s), 3.40 (3H, s), 2.23 (3H, s).

Step 3-Acetylamino-6-chloro-2 - [(1-methylimidazol-2-Pcarbonylindole) To a solution of 3-acetylamino-6-chloro-2 - [(N-methoxy-N- • methylamino) carbonyl] indole ( step 4; 50 mg, 0.175 mmol) in tetrahydrofuran (3.0 ml) cooled to -70 ° C, a solution in tetrahydrofuran (2.0 ml) of 2-lithiated 1-methylimidazole (prepared according to the procedure of Fraser, Robert was added. and others, Can J. Chem., 1985, 63, 3505.) The reaction mixture was allowed to warm to room temperature and was stirred for 2 h The mixture was poured into water (20 ml) and extracted with dichloromethane (20 ml). ml x 2). The extract Organic was dried (MgSO) and concentrated. The residual solid was purified by flash column chromatography eluting with ethyl acetate to yield 20 mg (36%) of the title compound as a yellow solid, m.p .: 205-207 ° C. ? -RMN (CDCI3) d: 11.69 (1 H, sa), 10.67 (1 H, sa), 8.40 (1 H, d, J = 8.8 Hz), 7.36 (1 H, d, J = 1.8, Hz) , 7.26 (1 H, s), 7.11 (1 H, s), 7.03 (1 H, dd, J = 8.8, 1.8 Hz), 4.15 (3H, s), 2.33 (3H, s). IR (KBr) v: 1695, 1580, 1540, 1470, 1400, 1360, 1240, 1200, 1160, 1025 cm "1. ik. EXAMPLE 125 3-Amino-6-chloro-2- (pyrjdine-2 »-eatbo? Íl) indole Step 1. E-chloro-S-nitroindol-^ -carboxylic acid To an ice-cold solution of acetic anhydride (90 ml) and concentrated nitric acid (70%, 10.3 ml) was added, in portions, for 20 minutes, acidic acid. -chloroindol-2-carboxylic acid (HW Ridon and JCT Tweddle, J. Chem. Soc, 1955, 3499: 18.16 g, 92.84 mmoles). The mixture was stirred for 2 h at 0 ° C and the resulting precipitates were collected by filtration and washed with a dichloromethane / hexane (1: 1) mixture, giving 12.6 g (56%) of the title compound as a solid. yellow. 1 H-NMR (DMSO-d 6) d: 13.41 (1 H, sa), 8.04 (1 H, d, J = 8.8 Hz), 7.62 (1 H, d, J = 1.8 Hz), 7.44 (1 H, dd , J = 1.8, 8.8 Hz).

Step 2. 6-Chloro-2- (N-methoxy-N-methylamino) carbonyl-3-nitride To a mixture of 6-chloro-3-nitroindol-2-carboxylic acid (step 1, 2. 35 g, 9.77 mmol) and NO-dimethylhydroxylamine hydrochloride (3.81 g, 39.1 mmol) in DMF (50 mL), a solution of dimethylformamide (15 mL) of WSC (5.61 g, 29.3 mmol) was added dropwise over the course of the reaction mixture. min. After stirring for 4 h, the mixture was diluted with diethyl ether (200 ml) and washed with water (100 ml x 4). The organic extract was dried (MgSO4) and the solvent was removed by evaporation. The crude product was recrystallized from ethyl acetate yielding 1.55 g (56%) of the title compound.

-NRM (DMSO-de) d: 13.48 (1 H, sa), 8.09 (1 H, d, J = 8.4 Hz), 7.68 (1 H, d, J = 1.5 Hz), 7.46 (1 H, dd, J = 1.8, 8.8 Hz), 3.51 (3H, s), 3.38 (3H, s).

EXAMPLE 3 6-Chloro-3-nitro-2- (pyridine-2-carbonyl) indole To a solution of 2-bromopyridine (548 mg, 3.47 mmol) in diethyl ether (8 ml) cooled to -70 ° C, n-BuLi 1.66 M (2.1 ml in hexane) was added dropwise. After stirring for 30 minutes, a solution of 6-chloro-2- (N-methoxy-N-methylamino) carbonyl-3-nitroindole (step 2, 328 mg, 1.16 mmol) in THF (8 ml) was added. . The mixture was allowed to warm to room temperature and stirring was continued for 5 h. Then, saturated ammonium chloride (20 ml) was added and the mixture was basified with saturated sodium bicarbonate (50 ml). The mixture was extracted with ethyl acetate (150 ml) and the extract was washed with brine (80 ml) and dried (Na2SO4). After removing the solvent by evaporation, the residue was purified by flash column chromatography eluting with ethyl acetate / hexane (1: 3) to yield 150 mg (43%) of the title compound. -RMN (CDCI3) d: 8.67 (1 H, gives J = 4.0 Hz), 8.24 (1 H, d J = 8.1 Hz), 8.12 (1 H, d, J = 8.8 Hz), 7.98 (1 H, dt , J = 1.8, 7.7 Hz), 7.57 (1 H, ddd, J = 1.1, 4.8, 7.7 Hz), 7.54 (1 H, d, J = 1.5 Hz), 7.38 (1 H, dd, J = 1.5 8.8 Hz). The signal due to NH was not observed.

Step 4: 3-Amino-6-chloro-2 pJ ^: dyne-2-carboniPndol A mixture of 6-chloro-3-nitro-2- (pyridine-2-carbonyl) dol (step 3, 92 mg, 0.30 mmol), ammonium chloride (8 mg, 0.15 mmol) and iron powder (89 mg, 1.52 mmole) in 70% aqueous ethanol (6 ml), heated to reflux for 2 h and then cooled and filtered through a pad of Celite. The bed was washed abundantly with a mixture of ethanol / ethyl acetate (1: 1 v / v) and the combined washings were subjected to evaporation. The residue was diluted with ethyl acetate (50 ml), washed with saturated aqueous sodium bicarbonate (30 ml) and dried (Na 2 SO 4). Removal of the solvent gave the product as crystals. p.f .: 186-187 ° C. -NRM (CDCI3) d: 11.02 (1 H, sa), 8J6-8J4 (1 H, m), 8.35 (1 H, d, J = 8.8 Hz), 7.94 (1 H, dt, J = 1.8, 7.7 Hz), 7.53 (1 H, d, J = 8.8 Hz), 7.48 (1 H, ddd, J = 1.5, 4.8, 7.7 Hz), 7.34 (1 H, d, J = 1.8, Hz), 6.97 (1 H, dd, J = 1.8, 8.4 Hz), 6.06 (2H, sa).

EXAMPLE 126 3-AcTylamino-6-chloro-2- (pyridine-2-carbonyl) indole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (pyridine-2-carbonyl) indole (example 125) and acetyl chloride. p.f .: 211-212 ° C (ethanol). -NRM (DMSO-d6) d: 12.02 (1 H, s a), 10.34 (1 H, s a), 8.82 (1 H, d, J = 4.4 Hz), 8.15-8.07 (2H, m), 7.85 (1 H, d, J = 8.8 Hz), 7.75-7.70 (1 H, m), 7.63 3450, 3-Amino-6-chloro-2 - (3-cyanobenzole) indole (Example 127) and 3-Amino-2- (3-aminocarbonylbenzoyl-6-chloroindole (Example 128) Step 1, 3-Amino-6-chloro-2- (3-cyanobenzoiP-1- (ethoxycarboniPindol) The title compound was prepared according to the procedure described in step 2 of example 1, starting with 4-chloro-2 - (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 2-bromo-3'-cyanoacetophenone - NMR (CDCl 3) d: 8.21 (1 H, d, J = 1.8 Hz), 8.03 (1 H, s), 7.94 (1 H, m), 7.80-7.72 (1 H, m), 7.63-7.52 (2H, m), 7.32 (1 H, dd, J = 8.4, 1.8 Hz), 6.10 (2H, sa), 3.88 (2H, q, J = 7.3 Hz), 0.95 (3H, t, J = 7.3 Hz).

Step 2. 3-Amino-6-chloro-2- (3-cyanobenzoiPindol (example 127) and 3-amino-2- (3-aminocarbonylbenzoyl) -6-chloroindole (Example 128) A mixture of 3-amino 6-chloro-2- (3-cyanobenzoyl) -1- (ethoxycarbonyl) indole (step 1, 10.4 g, 28 mmol) and potassium carbonate (20 g, 140 mmol) in ethanol (100 ml) and water (100 ml) was heated to reflux for 4 h. The mixture was cooled and concentrated and the residue was partitioned between water (100 ml) and ethyl acetate (250). The organic layer was dried (MgSO) and * & * * concentrated. The residual oil was removed by flash column chromatography eluting with hexane / ethyl acetate (2/1) to give; 3-Amino-6-chloro-2- (3-cyanobenzoyl) indole (example 127): yellow solid: 4.0 g (48%) mp .: 228-231 ° C. -NRM (DMSO-d6) d: 10.33 (1 H, sa), 8.15 (1 H, s), 8.09-8.02 (2H, m), 7.92 (1 H, d, J = 8.4 Hz), 7.77 (1 H, t, J = 7.3 Hz), 7.25 (1 H, d, J = 1.8, Hz), 7.04 (2H, sa), 6.96 (1 H, dd, J = 8.4, 1.8 Hz) y. 3-Amino-2- (3-aminocarbonylbenzoyl) -6-chloroindole (Example 128): yellow solid: 0J g (8%) m.p .: 132-150 ° C. ? -NRM (DMSO-d6) 10 d: 10.30 (1 H, sa), 8.23 (1 H, s), 8.28-8.02 (2H, m), 7.95-7.85 (2H, m), 7.65 (1 H, t, J = 7J Hz), 7.48 (1 H, sa), 7.25 (1 H, d, J = 1.8 Hz), 6.95 (1 H, dd, J = 8.4, 1.8 Hz), 6.90 (2H, sa) .

EXAMPLE 129 15 3-Acetylamino-2- (3-aminocarbonylbenzoyl) -6-chloroindole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-2- (3-aminocarbonylbenzoyl) -6-chloroindole (Example 128) and acetyl chloride. mp .: 243-20 247 ° C (ethyl acetate / hexane). -NRM (DMSO-de) d: 11.85 (1 H, s), 9.79 (1 H, s), 8.22 (1 H, s), 8.18-8.03 (2H, m), 7.83 (1 H, d, J = 7.7 Hz), 7.70-7.44 (4H, m), 7.12 (1 H, dd, J = 8.4, 1.8 Hz), 1.63 (3H, s). , ».. > .. »" >., ~ * .ifrj? ^ W? S3i & & amp; & -2 -2 EXAMPLE 30 The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (3-cyanobenzoyl) indole (example 127) and acetyl chloride. mp .: 185-187 ° C (ethyl acetate / hexane). ? -NRM (DMSO-d6) d: 11.91 (1 H, sa), 9.85 (1 H, sa), 8.12-8.04 (2H, m), 8.03-7.95 (1 H, m), 7.77-7.62 (2H , m), 7.46 (1 H, d, J = 1.8, Hz), 7.12 (1 H, dd, J = 1.8, 8.8 Hz), 1.64 (3H, s).

EXAMPLE 131 A mixture of 3-acetylamino-6-chloro-2- (3-cyanobenzoyl) idol (example 130, 2.7 g, 7.99 mmol) and potassium hydroxide (2.2 g, 40 mmol) in ethanol (100 ml) and water (100 g. ml), was heated to reflux for 5 h. The mixture was cooled and concentrated and the residue was partitioned between water (100 ml) and ethyl acetate (100 ml). The aqueous layer was separated and acidified with 2N aqueous hydrochloric acid, extracted with ethyl acetate (100 ml x 2) and the combined extracts were dried (MgSO4). After removing the solvent, the residual solids were recrystallized from ethyl acetate to yield 1.8 g (72%) of the title compound as brown solids. p.f .: 263-270 ° C. ? -NRM (DMSO-d6) d: 13.15 (1 H, s), 10.33 (1 H, s), 8.27 (1 H, s), 8.20-8.11 (1 H, m), 8.03-7.96 (1 H , m), 7.92 (1 H, d, J = 8.8 Hz), 7.70 (1 H, t, J = 7.6 Hz), 7.25 (1 H, d, J = 1"8 Hz), 6.96 (1 H, dd, J = 8.8, 1.8 Hz), 6.94 (2H, sa).

EXAMPLE 132 3-Acetylamino-2- (3-carboxybenzoyl) -6-chloroindole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-2- (3-carboxybenzoyl) -6-chloroindole (example 131) and acetyl chloride. p.f .: > 290 ° C (ethyl acetate). ? -NRM (DMSO-d6) d: 11.85 (1 H, s), 9.90 (1 H, s), 8.39 (1 H, sa), 8.20 (1 H, d, J = 7.7 Hz), 7.77 (1 H, d, J = 7.7 Hz), 7.65 (1 H, d, J = 8.8 Hz), 7.54-7.43 (2H, m), 7.09 (1 H, dd, J = 1.8, 8.4 Hz), 1.67 (3H , s).

EXAMPLE 133 3-Amino-6-chloro-2- (3-methoxycarbonylbenzoyl) indole A mixture of 3-acetylamino-6-chloro-2- (3-carboxybenzoyl) indole (example 132, 0.9 g, 2.5 mmol) and 10% HCl-MeOH (30 ml) was heated at 60 ° C for 8 h. The mixture was cooled and concentrated and the residue was partitioned between water (100 ml) and ethyl acetate (100 ml). The organic layer was separated, washed with brine (50 ml), dried (MgSO 4) and the solvent was removed by evaporation. The residual solid was purified by flash column chromatography eluting with hexane / ethyl acetate (2/1) to yield 0.5 g of the title compound as p.p .: 187-189 ° C (ethyl acetate / hexane). ? -NRM (DMSO-d6) d: 9.14 (1M, sa), 8.47 (1 H, dd, J = 1.8, 1.1 Hz), 8.20 (1 H, ddd, J = 7.7? ß, 1.1 Hz), 8.03 (1 H, ddd, J = 7.7, 1.8, 1.1 Hz), 7.69-7.58 (2H, m), 7.28 (1 H, d, J = 1.8 Hz), 6.97 (1 H, dd, J = 1.4, 8.4 Hz), 6.04 (2H, sa), 3.95 (3H, s).

EXAMPLE 134 3-Acetylamino-6-chloro-2- (3-methoxycarbonylbenzo) -Pindol The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (3-methoxycarbonylbenzoyl) indole (example 133) and acetyl chloride. mp: 190-193 ° C (ethyl acetate) -NMR (DMSO-d6) d: 9.80 (1 H, s), 8.52-8.41 (2H, m), 8.26 (1 H, d, J = 7.7 Hz) , 8.19 (1 H, d, J = 9.2 Hz), 8.98 (1 H, d, J = 7.7 Hz), 7.70-7.62 (1 H, m), 7.30 (1 H, d, J = 1.8 Hz), 7.09 (1 H, dd, J = 9.2, 1.8 Hz), 3.95 (3 H, s), 2.23 (3 H, s).

EXAMPLE 135 3-Acetylamino-2- (3-aminobenzoyl-6-chloroindole Step 1. 3-Amino-6-chloro-1-ethoxycarbonyl-2- (3-nitrobenzoiPndol) The title compound was prepared according to the procedure described in step 2 of Example 1, starting with 4-chloro- 2- | e ^^ Karbonylamino) benzonitrile (example 1, step 1) and 2-bromo-3'-nitroacetophenone. -RMN (CDCI3) d: 8.62-8.54 (1 H, m), 8.38-8.28 (1 H, m), 8.21 (1 H, d, J = 1.8 Hz), 8.04 (1 H, d, J = 7.7 Hz ), 7.63 (1 H, dd, J = 1.8, 8.1 Hz), 7.57 (1 H, d, J = 8.4 Hz), 7.33 (1 H, dd, J = 1.8, 8.1 Hz), 6.03 (2H, sa ), 3.88 (2H, q, J = 7.0 Hz), 0.94 (3H, t, J = 7.0 Hz).

Step 2. 3-Acetylamino-6-chloro-1- (ethoxycarboniP-2- (3-nitrobenzoiPindol) The title compound was prepared according to the procedure described in step 1 of example 2 (method A), from 3 -amino-6-chloro-1-ethoxycarbonyl-2- (3-nitrobenzoyl) indole (stage 1) and acetyl chloride.? -RMN (CDCI3) d: 9.18 (1 H, sa), 8.65-8.69 (1 H , m), 8.38-8.42 (1 H, m), 8.02-8.10 (1 H, m), 7.98 (1 H, s), 7.61-7.71 (2H, m), 7.18-7.25 (1 H, m) , 4.15 (2H, q, J = 7.0 Hz), 2.24 (3H, s), 1.17 (3H, t, J = 7.0 Hz).

Step 3. 3-Acetylamino-6-chloro-2- (3-nitrobenzoiPindol) The title compound was prepared according to the procedure described in step 2 of example 2 (procedure A), starting from 3-acetylamino- 6-Chloro-1- (ethoxycarbonyl) -2- (3-nitrobenzoyl) indole (step 2). 246-250 ° C. -NRM (CDC) d: 11.24 (1 H, s a), 9.87 (1 H, s a), 8.62 (1 H, s), 8. 46-8.36 (1 H, m), 8.17 (1H, d, J = 7J Hz), 7.90 (1H, d, J = 8.4 Hz), 7J2 (1H, dd, J = 7J, 8.1 Hz), 7.46 ( l ?, d, J = 1.5 dd, J = 1.5, 8.8 Hz), 1.98 (3H, s).

Step 4. 3-AcetylaR -2- (3-aminobenzoiP-6-chloro-inol) A mixture of 3-acetylamino-6-chloro-2- (3-nitrobenzoyl) indole (step 3, 2.68 g, 7.5 mmol), iron powder (1.7 g, 30 mmol) and ammonium chloride (0.8 g, 17 mmol) in 70% aqueous ethanol (70 ml), was heated to reflux for 1 h and then it was cooled and filtered through a pad of Celite. The filtrate was concentrated and the residue was partitioned between water (50 ml) and ethyl acetate (150 ml). The organic layer was separated, dried (MgSO 4) and the solvent was removed by evaporation to yield 2.6 g (quant.) Of the title compound as yellow amorphous solids. ? -NRM (CDCI3) d: 9.83 (1 H, sa), 8.63 (1 H, sa), 8.16 (1 H, d, J = 8.8 Hz), 7.35-7.21 (2H, m), 7.15-6.98 ( 3H, m), 6.88 (1 H, dd, J = 8.8, 1.8 Hz), 2.25 (3H, s). The signal due to NH2 was not observed.

EXAMPLE 136 3-Acetylamino-2- (3-aminobenzoyl) -6-chloroindole hydrochloride 3-Acetylamino-2- (3-aminobenzoyl) -6-chloroindole (example 135, 0.41 g, 1.3 mmol) in 10% HCl-MeOH (3.0 mL) for 10 minutes and then the solvent was removed by evaporation. The residual solid was recrystallized from ethanol / diethyl ether to give 320 mg (70%) of the title compound as a solid > 300 ° C. -NRM (DMSO-d6) d: 11.87 (1 H, sa), 9.85 (1 H, sa), 7.78-7.40 (6H, m), 7.12 (1 H, d, J = 8.4 Hz), 1.70 (3H , s).

EXAMPLE 137 3-Acetylamino-2- (3-acetylaminobenzo-P-6-chloroindole The title compound was prepared according to the procedure described in example 1, using 3-acetylamino-2- (3-aminobenzoyl) -6-chloroindole (example 135) and acetyl chloride. mp .: 225-228 ° C (ethyl acetate / hexane). -NRM (DMSO-d6) d: 10.59 (1 H, sa), 9.75 (1 H, sa), 9.45 (1 H, sa), 7.96 (1 H, d, J = 8.8 Hz), 7.93-7.82 ( 2H, m), 7.58-7.40 (3H, m), 7.04 (1H, d, J = 8.8 Hz), 2.17 (3H, s), 2.10 (3H, s).

EXAMPLE 138 3-Acetylamino-6-chloro-2- (3-methanesulfonylaminobenzoyl) -indole The title compound was prepared according to the procedure described in Example 19, employing 3-acetylamino-2- (3-aminobenzoyl) -6-chloroindole (example 135) and methanesulfonyl chloride. mp .: 133-142 ° C (ethyl acetate / hexane). -NRM (DMSO-de) d: 11.80 (1 H, sa), 9.90 (1 H, sa), 9.70 (1 H, sa), 7.65 (1 H, d, J = 8.8 Hz), 7.58 (1 H , sa), 7.49-7.40 (4H, m), 7.08 (1 H, d, J = 8.8 HeiET (3H, s), 0.86 (3H, s).

EXAMPLE 139 3-Acetylamino-6-chloro 2- (3-n, n-dimethylaminobenzoiPindol To a solution of 3-acetylamino-2- (3-aminobenzoyl) -6-chloroindole (Example 135, 0.89 g, 2.7 mmol) in acetonitrile (10 ml), aqueous formaldehyde (37%, 1.1 ml) and cyanoborohydride were added. sodium (0.28 g, 4.4 mmol). After stirring for 30 minutes, acetic acid (1.0 ml) was added and stirring was continued for a further 1.5 h. The mixture was concentrated, saturated aqueous sodium bicarbonate (30 ml) was added and the mixture was extracted with ethyl acetate (50 ml x 3). The organic layer was extracted with 2N aqueous hydrochloric acid (40 ml x 3). The acid extract and the aqueous layer were combined, basified with 2N aqueous sodium hydroxide (120 ml) and extracted with ethyl acetate (50 ml x 3). The organic layer was dried (MgSO 4) and concentrated and the residue was purified by flash column chromatography, eluting with hexane / ethyl acetate (2/1), to give 720 mg (67%) of the title compound that was recrystallized in hexane / ethyl acetate (440 mg, 41%) as a yellow solid. -NRM (CDCI3) d: 10.00 (1 H, sa), 8.45 (1 H, sa), 8.23 (1 H, d, J = 8.4 Hz), 8.44-8.36 (1 H, m), 7.28 (1 H, d, J = 1.8 Hz), 7.13-7.03 (3H, m), 7.00-6.93 (1 H, m), 3.02 (6H, s), 2.30 (3H, s).

EXAMPLE 140 3-Acetylamino-6-chloro-2- (3-n-n-dimethylaminobenzoi-Pindol hydrochloride The title compound was prepared from 3-acetylamino-6-chloro-2- (3-N, N-dimethylaminobenzoyl) mdol (Example 139) according to the procedure described in Example 136. MP: 245- 247 ° C (ethanol / diethyl ether) -NMR (DMSO-de) d: 11.85 (1H, sa), 9.84 (1H, sa), 7.75-7.40 (6H, m), 7.10 (1H, dd, J = 8.8, 1.8 Hz), 3.10 (6H, s), 1.69 (3H, s).

EXAMPLE 141 3-Acetylamino-6-chloro-2- (3,4-dihydroxybenzoyl) indole Step 1. [3,4-bis (methoxymethoxy) 1-phenoyl chloride). They were shaken together for 1 h, 4- (chloroacetyl) catechol (4.1 g, 22 mmol), chloromethyl methyl ether (3.7 ml, 44 mmol) and triethylamine. (12 ml) in tetrahydrofuran (50 ml), the mixture was poured into water (80 ml) and extracted with diethyl ether (80 ml x 2). The organic extract was washed consecutively with 2N aqueous sodium hydroxide (50 ml x 2) and water (50 ml), dried (MgSO 4) and the solvent was evaporated to give 4.7 g (78%) of the title compound as a pale brown solid. (The crude product was used in the next step without further purification). 1 H-NMR (CDCl 3) d: 7.78 (1 H, d, J = 2.2 Hz), 7.60 (1 H, dd, J = 8.4, 2.2 Hz), 7.23 (1 H, d, J = 8.4 Hz) , 5.32 (2H, s), 5.29 (2H, s), 4.65 (2H, s), ~ * n < m t 3.53 (3H, s), 3.52 (3H, s).

Step 2. 3-Amino-6-chloro-1-ethoxycarbonyl-2-y [3,4-bis (methoxymethoxy) Ibenzoi? Ndol The title compound was prepared according to the procedure described in step 2 of Example 1, from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (Example 1, step 1) and [3,4-b? S (methoxymethoxy)] phenacyl chloride (step 1). -NRM (CDCI3) d: 8.25 (1 H, d, J = 1.8 Hz), 7.61 (1 H, d, J = 2.2 Hz), 7.52 (1 H, d, J = 8.0 Hz) J.39 (1 H, dd, J = 8.4, 1.8, Hz), 7.29 (1 H, dd, J = 8.4, 1.8 Hz), 7.18 (1 H, d, J = 8.4 Hz), 5J2 (2H, sa), 5.29 (2H, s), 5.25 (2H, s), 3.86 (2H, q, J = 7.3), 3.52 (6H, s ), 0.91 (3H, t, J = 7.3 Hz).

Step 3-Amino-6-chloro-f 3,4, bis (methoxymethoxy) 1-benzoyl indole The title compound was prepared according to the procedure described in step 3 of Example 1, starting from 3-amino- 6- chloro-1-ethoxycarbonyl-2- [[3,4-bis (methoxymethoxy)] benzoyl] dol (step 2). ? -RMN (CDCI3) d: 7J3 (1 H, sa), 7.63 (1 H, d, J = 1.8 Hz), 7.52 (1 H, d, J = 8.8 Hz), 7.47 (1 H, dd, J = 8.8, 1.8 Hz), 7.28 (1 H, d, J = 8.4 Hz), 20 7.22 (1 H, d, J = 1.8 Hz), 7.02 (1 H, dd, J = 8.4, 1.8 Hz), 5.59 (2H sa), 5.32 (2H, s), 5.30 (2H, s), 3.54 (6H, s).

Step 4. 3-Acetylamino-6-chloro-2 í (3,4-dihydroxp benzoyljindol To a solution of 3-amino-6-chloro-2 - [[3,4-bis (methoxymethoxy)] benzoyl] indole (step 3, 0.50 g 1.3 mmole) in pyridine (1.0 ml) and dichloromethane (20 ml) cooled to 0 ° C, acetyl chloride (0.10 ml, 1.40 mmole) was added.After stirring for 1 h at room temperature, the reaction was poured into water (20 ml) and extracted with dichloromethane (30 ml x 2). The organic extracts were dried (MgSO) and the solvent was removed by evaporation. The residue was dissolved in dichloromethane (30 ml), trifluoroacetic acid (0.50 ml) was added and the mixture was heated to reflux for 5 h. The mixture was cooled, poured into water and extracted with ethyl acetate (80 ml x 2). The organic extracts were dried (MgSO 4) and the solvent was removed by evaporation. The residual oil was purified by flash column chromatography eluting with hexane / ethyl acetate (1/3) to give 80 mg (20%) of the title compound. Recrystallization from ethyl acetate / hexane afforded the title compound as a yellow solid, m.p .: 193-200 ° C. -NRM (CDCI3) d: 11.64 (1 H sa), 9.66 (1 H, sa), 7.58 (1 H, d, J = 8.4 Hz), 7.41 (1 H, J = 1.5 Hz), 7.24 (1 H, d, J = 2.2 Hz), 7.15 (1 H, d, J = 8.8, 1.8 Hz), 7.08 (1 H, dd, J = 8.8, 1.5 Hz), 6.80 (1 H, d, J = 8.4 Hz ), 1.98 (3H, s). The signal due to OH was not observed. 3- (3-amino-6-chloroindol-2-carbon-P-benzenesulfonamide) Step 1. 3- [3-Amino-6-chloro-1- (ethoxycarbonolpanedol-2-carbonylbenzenesulfonamide) The title compound was prepared according to the procedure described in step 2 of Example 1, starting from 4 -chloro-2 (ethoxycarbonylamino) benzonitrile (Example 1, step 1) and 3-bromoacetylbenzenesulfonamide (T. Fujikura, K. Nígata, S. Hashimoto, K. Imai and T. Takenaka, Chem. Pharm. Bull. , 1982, 30, 4092-4101).-NMR (DMSO-de) d: 8.14-8.07 (3H, m), 7.94 (1 H, da, J = 7.7 Hz), 7J8 (1 H da, J = 7.7 Hz), 7.65 (1 H, t, J = 7.7 Hz), 7.47 (2H, sa), 7.45 (1 H, dd, J = 1.8, 8.4 Hz), 7.38 (2H, sa), 3.75 (2H, q, j = 7.0 Hz), 0.79 (3H, t, J = 7.0 Hz).

Step 2. 3- (3-Amino-6-chloroindol-2-carbon-P-benzenesulfonamide) The title compound was prepared according to the procedure described in step 2 of Example 1, employing 3- [3-amino-6 -chloro-1- (ethoxycarbonyl) indole-2-carbonyl] benzenesulfonamide (step 1) .pf: 125-127 ° C (2-propanol / toluene). -NRM (DMSO-de) d: 10.31 (1H, sa ), 8.15 (1 H, sa), 8.02-7.93 (2H, m), 7.92 (1 H, d, J = 8.8 Hz), 7.75 (1 H, t, J = 7.7 Hz), 7.46 (2H, sa ), 7.24 (1H, d, J = 1.5 Hz), 6.96 (1 H, dd, J = 1.8, 8.4 Hz), 6.98-6.94 (2H, m).

• The title compound was prepared according to the procedure described in Example 19, employing 3- (3-amino-6-chloroindol-2-carbonyl) benzenesulfonamide (Example 142) and acetyl chloride. p.f. 250-151 ° C (ethanol / toluene). -NRM (DMSO-de) d: 11.89 (1 H, sa), 9.83 (1 H, sa), 8.14 (1 H, sa), 8.03 (1 H, da, J = 8.1 Hz), 7.90 (1 H) , da, J = 7.7 Hz), 7.69 (1 H, t, J = 7.7 ^? 10 Hz), 7.68 (1H, d, J = 8.8 Hz), 7.46 (2H, s), 7.45 (1 H, d, J = 1.8 Hz), 7.13 (1H, dd, J = 1.8, 8.8 Hz), 1.64 (3H, s).

EXAMPLE 144 3-Amino-6-chloro-2- (3-methylcyclohexylcarbonyl) indole Step 1. 1-Bromoacetyl-3-methylenecyclohexane (a mixture of cis and trans) The title compound was prepared according to the procedure described in H. McKennis, Jr., LB Turnbull, E.R. Bowman and E.

Tamaki, J. Org. Chem., 1963, 28-383-387, from 1-acetyl-3-methylcyclohexane (N. Dufort et al., Can. J. Chem., 1968, 46, 1073). -NRM (CDCI3) d: 3.98 (2H, s), 2.80-2.65 (1 H, m), 1.95-1.20 (9H, m), 1.92 (3H, d, J = 6.6 Hz. methylcyclohexylcarboniPindol The compound ^ the title was prepared according to the procedure described in Example 1, from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (Example 1, step 1) and 1-bromoacetyl-3-methylcyclohexane (step 1) ). ^ -RMN (CDCI3) d: 8.14 (1 H, d, J = 1.8 Hz), 7.45 (1 H, d, J = 8.4 Hz), 7.26 (1 H, dd, J = 1.8, 8.4 Hz), 5.66 (2H, sa), 4.43 (2H, q, J = 0 7.0 Hz), 2.90-2.75 (1 H, m), 1.89-0.90 (9H, m), 1.42 (3H, t, J = 7.0 Hz), 0.88 (3H, d, J = 6.6 Hz).

Step 3. 3-Amino-6-chloro-2- (3-methylcyclohexycarbonylPndol) The title compound was prepared according to the procedure described in step 3 of Example 1, starting from amino-6-chloro-1-ethoxycarbonyl-2- (3-methylcyclohexylcarbonyl) idol (step 2) mp: 140-142 ° C (hexane / ethyl acetate). ? -RMN (CDCI3) d: 7.57 (1 H, s a), 7.48 (1 H, d, J = 8.4 Hz), 7.26 (1 H, d, J = 1.5 Hz), 7.02 (1 H, dd, J = 1.5, 8.4 Hz), 5.46 (2 H, s a), 2.84-2.75 (1 H, m), 1.93-1, 03 (9H, m), 0.95 (3H, d, J = 6.6 Hz). 3-Acetylamino-6-chloro-2- (3-methylcyclohexylcarbonyl) indole The title compound was prepared according to the procedure described in Example 19, employing 3-amino-6-chloro-2- (3-methylcyclohexylcarbonyl) indole (Example 144) and acetyl chloride. mp .: 202-203 ° C (ethyl acetate / hexane). 1 H-NMR (CDCl 3) d: 9.98 (1 H, sa), 8.27 (1 H, sa), 8.25 (1 H, d, J = 9.2 Hz) 7.31 (1 H, s), 7.08 (1 H, d , J = 7.7 Hz), 2.94. (1 H, t a, J = 8.2 Hz), 2.29 (3 H, s), 1.94-1.00 (9H, m), 0.96 (3H, d, J = 6.2 Hz).

EXAMPLE 146 3- (N-Acetyl-n-methylamino) -2-benzoyl-6-chloroindole To a solution of 3-acetylamino-2-benzoyl-6-chloro-1- (ethoxycarbonyl) indole (Example 2, step 1, 900 mg, 2.34 mmol) in dimethylformamide (10 ml) was added sodium hydride (dispersion at 60 ° C). % w / w in mineral oil, 94 mg, 2.34 mmol). The mixture was stirred for 0.5 h, then iodomethane (0.22 mL, 3.51 mmol) was added dropwise and stirring was continued for 19 h. The reaction mixture was poured into water (50 ml) and extracted with diethyl ether (100 ml x 2). The extracts were washed consecutively with water (50 ml) and brine (50 ml), dried (MgSO 4) and the solvent was removed by evaporation. The residual oil dissolved in ---- * _._? -? -. at 85%, 264 mg, 4.0 concentrated and the residue was partitioned between water (100 ml) and diethyl ether (100 ml). The organic layer was separated and washed consecutively with water (100 ml) and brine (100 ml), dried (MgSO 4) and the solvent was removed by evaporation. The residual solids were recrystallized from dichloromethane / hexane, yielding 165 mg (63%) of the title compound as a yellow powder, m.p .: 232-235 ° C. -NRM (CDCI3) d: 9.18 (1 H, sa), 7J4 -7.35 (7H, m), 7.22 (1 H, dd, J = 1.5, 8.4 Hz), 2.97 (3H, s), 1.86 (3H, s). IR (KBr) v: 1620, 1320, 1240 cm " EXAMPLE 147 3- (N-Acetyl-n-methylamino) -6-chloro-2- (3-methylbenzoiPindol) The title compound was prepared from 3-acetylamino-6-chloro-1-ethoxycarbonyl-2- (3-methylbenzoyl) indole (Example 22, step 1) according to the procedure described in Example 146. pf : 166-171 ° C (ethanol / ethyl ether)? -NMR (CDCl 3) d: 9.48 (1 H, sa), 7.65-7.35 (6H, m), 7.21 (1 H, dd, J = 8.8. 1.8 Hz), 2.96 (3H, s), 2.42 (3H, s), 1.88 (3H, s).

EXAMPLE 148 3- (N-Acetyl-n-methalamine) -6-chloro-2- (3-chlorobenzoyl) indole The title compound was prepared from 3-acetylamino-6-chloro-2- (3-chlorobenzoyl) -1 - (ethoxycarbonyl) indole (Example 31, step 1) according to the procedure described in Example 146. pf : 202-203 ° C (ethyl acetate) -NMR (CDCl 3) d: 9.16 (1 H, sa), 7.79-7.39 (6H, m), 7.23 (1 H, dd, J = 1.8, 8.4 Hz), 3.02 (3H, s), 1.86 (3H, s).

EXAMPLE 149 3- (N-Acetyl-n-methylamino) -6-chloro-2- (cyclohexylcarbonyl) indole Step 1. 3-Acetylamino-6-chloro-2- (cyclohexanecarbonyl) -1- (ethoxycarbonyl) ethylene The title compound was prepared according to the procedure described in step 1 of Example 2 (Method A), from 3-acetylamino-6-chloro-2-cyclohexylcarbonyl-1 - (ethoxycarbonyl) indole (Example 93, step 1). -NRM (CDCI3) d: 8.80 (1 H, s a), 8.12 (1 H, d, J = 1.5 Hz), 7.87 (1 H, d, J = 8.8 Hz), 7.27 (1 H, dd, J = 1.5, 8.8 Hz), 4.50 (2H, q, J = 7.0 Hz), 2.77 (1 H, tt, J = 2.6, 0.4 Hz), 2.22 (3H, s), 1.80-1.23 (10H, m), 1.47 (3H, t, J = 7.0 Hz). (cyclohexanecarboniPindol) The title compound was prepared from 3-acetylamino-6-chloro-2-cyclohexylcarbonyl-1- (ethoxycarbonyl) idol (step 1) according to the procedure described in Example 146. MP: 162-163 ° C (ethyl acetate / hexane) - NMR (CDCl 3) d: 9.07 (1 H, sa), 7.46-7.43 (2H, m), 7.20 (1 H, dd, J = 1.8, 8.8 Hz), 3.37 (3H, s), 3.07-2.96 (1 H, m), 1.88 (3H, s) 1.88-1.25 (10H, m) EXAMPLE 150 3- (N-Acetyl-n-carboxymethylamino) -2-benzoyl-β-chloroindole Step 1: 3- (N-Acetyl-N-methoxycarbonylmethalamine) -2-benzoyl-6-chloro-1- (ethoxycarbonyl) The title compound was prepared according to the procedure described in Example 146, from 3-acetylamino-2-benzoyl-6-chloro-1 - (ethoxycarbonyl) indole (Example 2, step 2) and methyl bromoacetate - NMR (CDCl 3) d: 8.30 (1H, d J = 1.8 Hz), 7.89 (1 H, d, J = 8.4 Hz), 7.77-7.55 (2 H, m), 7.52-7.36 (4H, m), 4.64 (1 H, d, J = 17.7 Hz) , 4.18 (2H, d, J = 7.0 Hz), 3.98 (1 H, J = 17.7 Hz), 3.59 (3H, s), 1.97 (3H, s), 1.02 (3H, t, J = 7.0Hz) The title compound was prepared according to the procedure described in step 2 of Example 2 (Procedure A), starting with 3- (N-acetyl-N-methoxycarbonyl-2-phosphino) -2-benzoyl-6-chloro-1- (ethoxycarbonyl) dol (step 1) mp 148-154 ° C (dichloromethane) -NMR (DMSO-de) d: 12.53 (1H, sa), 12.17 (1H, sa), 7.85 (1H , d, J = 8.8 Hz), 7.78-7.62 (3H, m), 7.62-7.51 (3H, m), 7.22 (1 H, dd, J = 1.8, 8.8 Hz), 3.96 (1 H, d J = 17. 2 Hz), 3.66 (1 H, d, J = 17.2 Hz), 1.80 (s, 3H). # 10 EXAMPLE 151 2-Benzoyl-6-chloro-3- (n, n-dimethylamino) indole Step 1. 2-Benzoyl-6-chloro-1-ethoxycarbonyl-3- (N, N-dimethylamino) indole To a solution of 3-amino-2-benzoyl-6-chloro-1 (ethoxycarbonyl) indole (Example 1, step 2, 1.0 g, 2.9 mmol) in acetonitrile (20 ml) was added • formaldehyde (37% solution by weight of water, 1.2 g, 14.5 mmol) and sodium borohydride (380 mg, 5.8 mmol) and the mixture was acidified (ph 6) with glacial acetic acid. After stirring for 19 h, the reaction mixture The mixture was concentrated and the residue was partitioned between 4N aqueous NaOH (20 ml) and diethyl ether (100 ml). The organic extract was separated, washed consecutively with water (100 ml) and brine (100 ml) and dried (MgSO 4). After removing the solvent, the residue was purified by flash column chromatography eluting with ethyl acetate / hexane (1:10) to give 590 mg of the title compound as a yellow oil. tic: Rf = 0.6 (33% ethyl acetate in hexanes).

Step 2. 2-Benzoyl-6-chloro-3- (N, N-dimethylamino) ndol The title compound was prepared according to the procedure described in step 2 of Example 2, starting from 2. -benzoyl-6-chloro-1-ethoxycarbonyl-3 (N, N-dimethylamino) indole (step 1). p.f .: 178-180 ° C (diethyl ether / hexane). -NRM (CDCI3) d: 8.36 (1 H, s a), 7.88-7J5 (3H, m), 7.60-7.42 (3H, m), 7.29 (1 H, d, J = 1.8, Hz), 7.00 (1 H, dd, J = 1.8, 8.8 Hz), 2.81 (6H, s).

IR (KBr) v: 1600, 1560, 1320, 980 cm "1.

EXAMPLE 152 3-Acetylamino-2-benzoyl-6-nitroindole Step 1. 2- (Ethoxycarbonylamino, -4-nitrobenzontrotyl) The title compound was prepared according to the procedure described in step 1 of Example 1 (Method B), starting from 2-amine-4-nitrobenzon. Trilo.tic: Rf = 0.45 (33% ethyl acetate in hexanes) "TO-.. . : •. *. • _. -or-x: with the procedure described in step 2 of Example 1, starting with 2- (ethoxycarbonylamino) -4-nitrobenzonitrile (step 1) and 2-bromoacetophenone. -NRM (CDCI3) d: 9.13 (1 H, d, J = 1.8 Hz), 8.20 (1 H, dd, J = 1. 8, 8.6 Hz), 7J4 (1 H, d, J = 8.6 Hz), 7J7-7.43 (5H, m) 5.67 (2H, s a), 3.83 (2H, q, J = 7.3 Hz), 0.89 (3H, t, J = 7.3 Hz).

Step 3. 3-Acetylamino-2-benzoyl-1- (ethoxycarbonyl) -6-nitroindole The title compound was prepared according to the procedure described in step 1 of Example 2 (Method A), starting from of 3-amino-2-benzoyl-1- (ethoxycarbonyl) -6-nitroindole (step 2). tic: Rf = 0.2 (50% ethyl acetate in hexanes).

Step 4. 3-Acetylamino-2-benzoyl-6-nitroindol The title compound was prepared according to the procedure described in step 2 of Example 2 (Procedure A), starting from 3-acetylamino-2-benzo L-1- (ethoxycarbonyl) -6-nitridendol (step 3). p.f .: 234-236 ° C. ? -NRM (DMSO-de), d: 12.3 (1 H, sa), 9.87 (1 H, s), 8.34 (1 H, d, j = 2.2 Hz), 7.95 (1 H, dd, J = 2.2, 8.8, Hz), 7.81 (1 H, d, J = 8.8 Hz), 7J8-7.51 (5H, m), 1.69 (3H, s) IR (KBr) v: 1675, 1605, 1540, 1355, 1250, 1020, 970, 850, 840 cm "1. gggg Hydrophilic 3-acetylamino-2-benzoyl-6-nitroindole (Example 152, 180 mg, 0.56 mmol) was subjected to hydrolysis in the presence of palladium on activated carbon (5%, 18 mg) in ethanol (30 ml) at atmospheric pressure, during 4 h. The catalyst was removed by filtration and the filtrate was concentrated. The residue was purified by flash column chromatography eluting with 0 to 50% ethyl acetate in hexanes and the product was recrystallized from a methanol / ethyl acetate / hexane mixture to give 85 mg of the title compound, mp: 219- 221 ° C. -NRM (DMSO-d6), d: 10.9 (1 H, sa), 9.54 (1 H, s), 7.44-7.66 (5H, m), 7.38 (1 H, d, J = 9.2 Hz), 6.47- 6.45 (2H, m), 5.35 (2H, s), 1.69 (3H, s).

EXAMPLE 154 3-Acetylamino-2-benzoyl-5-methoxyindole Step 1. 5-Methoxy-3-nitroindol-2-carboxylic acid The title compound was prepared according to the procedure described in step 1 of Example 125, using 5-methoxyindole-2-carboxylic acid. procedure described in step 2 of Example 125, employing 5-methoxy-3-nitroindol-2-carboxylic acid (1-cap 1). -NRM (CDCI3) d: 9.64 (1H, s a), 7.62 (1 H, d, J = 8.8 Hz), 7.49 (1H, d, J = 2.2 Hz), 7.14 (1H, dd, J = 2.2, 8.8 Hz), 4.02 (3H, s), 3.87 (3H, s), 3. 45 (3H, s).

Step 3. 3-Amino-5-methoxy-2-r (N-methoxy-N-methylamine) carbon-pyrol A mixture of 5-methoxy-2- (N-methoxy-N-methylamino) carbonyl-3-nitroindole (step 2, 110 mg, 0.39 mmole), ammonium chloride (11 mg, 0.20 mmole) and iron powder (115 mg, 1.97 mmole) in 70% aqueous ethanol (10 ml) was heated to reflux for 2 h, then cooled and filtered through a pad of Celite. The layer was washed abundantly with a mixture of ethanol / ethyl acetate (1: 1 v / v) and the combined washings were evaporated. The residue was diluted with ethyl acetate (50 ml), washed with saturated aqueous sodium bicarbonate (30 ml) and dried (Na 2 S 4). Removal of the solvent gave the product as an oil, tic: Rf = 0.5 (50% ethyl acetate in hexanes).

The title compound was prepared according to the procedure described in Example 19, employing 3-amino-5-methoxy-2- (N-methoxy-N-methylamino) carbonyl-indole (step 3) and acetyl chloride. MS m / z: 291 [M +] Step 5. 3-Acetylamino-2-benzoyl-5-methoxyindole The title compound was prepared in a manner analogous to the procedure described in step 3 of Example 125, employing 3-acetylamino-5-methoxy-2- (N-methoxy) -N-methylamino) carbonyl idol (step 4) and phenylmagnesium bromide. p.f. : 258-260 ° C. NMR (CDCl 3) d: 9.12 (1 H, sa), 7.99 (1 H, d, J = 8.4 Hz), 7.98 (1H, s), 7.50-7.61 (4H, m), 7.11-7.36 (3H, m ), 3.91 (3H, s), 1.57 (3H, s) EXAMPLE 155 3-Acetylamino-2-benzoyl-6-methoxyindole Step 1. Methyl 6-methoxy-3-nitroindol-2-carboxylate The title compound was prepared according to the procedure described in step 1 of Example 125, employing methyl 6-methoxyindole-2-carboxylate. 1 H NMR (DMSO-d6) d: 7.89 (1 H, d, J = 9.2 Hz), 7.06 (1 H, dd, J = 2.2, 9.2 Hz), 7.01 (1 H, d J = 2.2 s) , 3.83 (3H, s). The signal due to NH of the indole was not observed. Step 2. 6-Methoxy-3-nitro-1,2-carboxylic acid To a solution of methyl 6-methoxy-3-nitroindol-2-carboxylate (step 1) in ethanol (10 ml) and water (5). ml), K2C? 3 was added and the mixture was stirred for 4 h at 40 ° C. The mixture was acidified with 2N HCl and extracted with ethyl acetate (20 ml x 2). The organic layer was washed with brine (10 ml) and dried (MgSO 4). Removal of the solvent gave the product as an oil, tic: Rf = (50% ethyl acetate in hexanes).

Step 3. 3-Acetylamlan-2-benzoyl-6-methoxyol The title compound was prepared according to the procedure described in Example 154, using 6-methoxy-3-nitroindol-2 acid. -carboxylic (stage 2) mp: 144-146 ° C. NMR (CDCl 3) d: 10.16 (1 H, s a), 8.32 (1 H, s a), 8.20 (1 H, d, J = 9.2 Hz), 7.33-7J9 (5H, m), 6.76 (1 H, dd, J = 2.2., 9.2 Hz), 6.63 (1 H, d J = 2. 2. Hz), 3.80 (3H, s), 1.58 (3H, s).

EXAMPLE 156 3-Acetylamino-2-benzoyl-5-fluoroindole The title compound was prepared according to the procedure described in Example 154 using 5-fluoroindole-2-carboxylic acid. p.f .; 80-82 ° C. 1 H NMR (CDCl 3) d: 9.68 (1 H, sa), 8.30 (1H, sa), 7.93 (1 H, d, J: 9.9 Hz), 7J9-7.83 (2H, m), 7.53-7.65 (3H, m), 7.10-7.25 (2H, m), 2.24 (3H, s).

EXAMPLE 157-EXAMPLE 353 The compounds described below were prepared from 3-amino-2-benzoyl-6-chloroindole (Example 1) and the acid chloride or acid anhydride required and available on the market, in accordance with • 10 procedure described in Procedure B of Example 2.

EXAMPLE 157 2-Benzoyl-6-chloro- (tert-butylacetylamino) indole, MS m / z: 367 f (M-H) 1.

EXAMPLE 158 2-Benzoyl-3- (2-bromobenzamido) -6-chloroindole, MS m / z: 453 T (M-H) 1.

• EXAMPLE 159 2-Benzoyl-3- (3-bromobenzamido) -6-chloroindole, MS m / z: 453 I (M-H) 1. EXAMPLE 160 2-Benzoyl-3- (bromoacetylamino) -6-chloroindole, MS m / z: 389 r (M-H) 1.

EXAMPLE 161 2-Benzoyl-3- (4-bromobenzamido) -6-chloroindole. MS m / z: 453 T (M-H) 1.

EXAMPLE 162 2-Benzoyl-6-chloro-3- (heptadeconoylamino) indole, MS m / z: 521 f (M-H) 1.

EXAMPLE 163 2-Benzoyl-6-chloro-3- (lauroylamino) indole, HPLC f Column: SHISEIDO CAPCELLPAK C18 UG120, 150 X 2.0 mm: • 10 Eluvente: MeCN: KH2PO? 50 mM (ph 3 with 2 M HCl) = 10 / 90-60 / 401: Tret. 11.58 min.

EXAMPLE 164 2-Benzoyl-6-chloro-3- (3,4-dichlorobenzamido) indole. MS m / z: 443 L? M-H.I.

EXAMPLE 165 2-Benzoyl-6-chloro-3- (3,5-dichlorobenzamido) indole. MS m / z: 441 T (M-H) 1.

EXAMPLE 166 2-Benzoyl-6-chloro-3- (decanoylamino) indole. MS m / z: 423 I (M-H) 1.

EXAMPLE 167 2-Benzoyl-6-chloro-3- (2-furoylamino) indole. MS m / z: 363 f (M-HH.

EXAMPLE 168 2-Benzoyl-6-chloro-3- (4-fluorobenzamido) indole. MS m / z: 391 KM-H.I.

• EXAMPLE 169 2-Benzoyl-6-chloro-3- (2-iodobenzamido) indole. MS m / z: 499 KM-HH.

EXAMPLE 170 2-Benzoyl-6-chloro-3- (heptafluorobutyrylamino) indole. MS m / z: 465 I (M-H) 1.

• EXAMPLE 171 2-Benzoyl-6-chloro-3- (4-trifluoromethylbenzamido) indole. MS m / z: 441 f (M-H) " EXAMPLE 172 15 2-Benzoyl-6-chloro-3- (n- (4-methylphenylsulfonyl-P-1-phenylalanylaminol indole MS m / z: 521 KM-HR EXAMPLE 173 2-Benzoyl-6-chloro-3- (hexanoylamino) indole. MS m / z: 367 f (M-H) 1. EXAMPLE 174 2-Benzoyl-6-chloro-3- (octanoylamino) indole. MS m / z: 395 T (M-H) 1.

EXAMPLE 75 2-Benzoyl-6-chloro-3- (2-ethylhexanoylamino) -indole. MS m / z: 395 T (M-H) 1 EXAMPLE 176 5 2-Benzoyl-6-chloro-3- (3-fluorobenzamido) indole. MS m / z: 391 HM-HV EXAMPLE 177 2-Benzoyl-6-chloro-3- (heptanoylamino) indole. MS m / z: 381 f.M-HV • 10 EXAMPLE 178 2-Benzoyl-6-chloro-3- (phenoxyacetylamino) indole. MS m / z: 403 I (M-H) " EXAMPLE 179 2-Benzoyl-6-chloro-3- (2-propylvalerylamino) indole. MS m / z: 395 F (M-H) ' EXAMPLE 180 2-Benzoyl-6-chloro-3- (cinnamoylamino) indole. MS m / z: 399 f (M-H) ' EXAMPLE 181 2-Benzoyl-6-chloro-3- (phenylacetylamino) indole. MS m / z: 387 T (M-H) ' EXAMPLE 182 2-Benzoyl-6-chloro-3- (4-methoxybenzamido) indole. MS m / z: 403 [(M-H) "EXAMPLE 83 2-Benzoyl-6-chloro-3- (3-methylthiopropionyl-amino) indole MS m / z: 371 [(M-H)" EXAMPLE 184 5 2-Benzoyl-6-chloro-3- (2-methoxybenzamido) indole. MS m / z: 403 f (M-H) ' EXAMPLE 185 2-Benzoyl-6-chloro-3- (palmitoylamino) indole. MS m / z: 507 [(M-H) " • EXAMPLE 186 2-Benzoyl-6-chloro-3- (3-phenoxypropionylamino) indole. MS m / z: 417 f (M-H) " EXAMPLE 187 2-Benzoyl-6-chloro-3- (3-methacryloylamino) indole. MS m / z: 337 f (M-H) '15 EXAMPLE 188 2-Benzoyl-6-chloro-3- (3,5-dinitrobenzamido) indole. MS m / z: 463 [(M-H) ' EXAMPLE 189 2-Benzoyl-6-chloro-3- (2-chloro-2-phenylacetylamino) indole. MS m / z: 421 f (M + H, 1 EXAMPLE 190 2-Benzoyl-6-chloro-3- (4-tert-butylbenzamidoindigo) MS m / z: 429 f (MH 1 EXAMPLE 191 2-Benzoyl-6-chloro-3- (5-chlorovalerylamido) indole. MS m / z: 387 (fM-H) 1 EXAMPLE 192 2-Benzoyl-3- (2-bromopropionylamino) -6-chloroindole. MS m / z: 402 [(M-H) "1 EXAMPLE 193 2-Benzoyl-6-chloro-3- (2-chloro-4-nitrobenzamido) indole. MS m / z: 452 [(M-H) 1 EXAMPLE 194 2-Benzoyl-6-chloro-3- (4-chloromethylbenzamido) indole. MS m / z: 421 f (M-H) 1 EXAMPLE 195 2-Benzoyl-6-chloro-3- (3-chloropropionylamino) indole. MS m / z: 359 f (M-H) 1 EXAMPLE 196 2-Benzoyl-6-chloro-3- (3-trans-crotonylamino) indole. MS m / z: 337 [(M-H)] EXAMPLE 197 2-Benzoyl-6-chloro-3- (2-chloropropionylamino) indole. MS m / z: 359 f (M-H) 1 EXAMPLE 198 2-Benzoyl-6-chloro-3- (4-chlorobutyrylamino) -indole. MS m / z: 373 [(M-H 1 : ^ and EXAMPLE 199 2-Benzoyl-6-chloro-3- (3-chloro-2,2-dimet? l-propyronylamino) indole. MS m / z: 387 r (M-H) 1 • EXAMPLE 200 2-Benzoyl-6-chloro-3- (10-undecenolamino) nolol. MS m / z: 435 [(M-H) l EXAMPLE 201 2-Benzoyl-6-chloro-3- (undecanoylamino) indole. MS m / z: 437 [(M-H) l 10 EXAMPLE 202 2-Benzoyl-6-chloro-3- (4-cyanobenzamido) indole. MS m / z: 398 f (M-H) 1 EXAMPLE 203 2-Benzoyl-6-chloro-3- (4-chlorophenoxyacetimlamino) indole. MS m / z: 437 T (M-H) 1 EXAMPLE 204 2-Benzoyl-6-chloro-3- (4-chlorobenzamido) indole. MS m / z: 407 [(M-H) ir (M-Hp EXAMPLE 205 2-Benzoyl-6-chloro-3- (nonanoylamino) indole, MS m / z: 409 f (M-H) 1 EXAMPLE 206 2-Benzoyl-6-chloro-3- (3-nitrobenzamido) dol. MS m / z: 418 [(M-H) 1 EXAMPLE 207 2-Benzoyl-6-chloro-3- (pentafluorobenzamido) dol. MS m / z: 463 f (M-H) 1 EXAMPLE 208 2-Benzoyl-6-chloro-3- (trichloroacetylamino) dol. MS m / z: 423 f (M-H) 1 EXAMPLE 209-Benzoyl-6-chloro-3- (3-nitrophenoxyacetylammon) indole, MS m / z: 448 f (M-H) 1 EXAMPLE 210 2-Benzoyl-6-chloro-3- (4-nitrobenzamido) dol. MS m / z: 418 T (M-H) 1 EXAMPLE 211 2-Benzoyl-6-chloro-3- (1-naphtholamino) indole. MS m / z: 423 f (M-H) 1 EXAMPLE 212 2-Benzoyl-6-chloro-3- (2-naphthoylamino) indole. MS m / z: 423 [(M-H)] 606 f (M-H) 1 EXAMPLE 214-Benzoyl-6-chloro-3-rn- (4-nitrophenylsulfonyl) -1-phenylalanylaminool indole. MS m / z: 601 f (M-H) 1 EXAMPLE 215 2-Benzoyl-6-chloro-3- (stearoylamino) indole. MS m / z: 535 f (M-H) 1 EXAMPLE 216 3- [f (2-benzoyl-6-chloro) -indol-3-inamino-carbonyl-n-butanoate, MS m / z: 411 [(M-HV1 EXAMPLE 217-Benzoyl-6-chloro-3- (2-trifluoromethyl-benzamido) indole. HPLC TC column: SHISEIDO CAPCELLPAK Cl UG120. 150 x 2.0 mm: Eluvente: MeCN: CH3CO2NH4 0.01 M = 50 / 50-90 / 101: Tret. = 5.52 min EXAMPLE 218-Benzoyl-6-chloro-3- (3-trifluoromethylbenzamido) indole. MS m / z: 441 ((M-H) 1 EXAMPLE 219 2-Benzoyl-6-chloro-3- (2,4,6-trichlorobenzamido) indole, MS z / z: 475 f (M-H) 1 EXAMPLE 220 2-Benzoyl-6-chloro-3- (3-methylbenzamido) indole. MS m / z: 387 T (M-H) 1 EXAMPLE 221 2-Benzoyl-6-chloro-3- (4-methylbenzamido) indole. MS m / z: 387 [(M-H)] EXAMPLE 222 2-Benzoyl-6-chloro-3- (2-methylbenzamido) indole. HPLC [Column: SHISEIDO CAPCELLPAK Cl UG120. 150 x 2.0 mm: Eluvente: MeCN: CH3CO? NH4 0.01 M = 50 / 50-90 / 101: Tret. = 5.31 min EXAMPLE 223 2-Benzoyl-6-chloro-3- (myristoylamino) indole, MS m / z: 479 f (MH) 1 ^ EXAMPLE 224 2-Benzoyl-6-chloro-3- (3,5,5-trimethylhexanoylamino) indole . MS m / z: 409 f (M- 20 H) 1 EXAMPLE 225 2-Benzoyl-6-chloro-3- (4-phenylbenzamido) dol. MS m / z: 449 [(M-H)] EXAMPLE 226 2-Benzoyl-6-chloro-3- (3,3-dimethylacrylolamin) nol. MS m / z: 351 Í.M-HH EXAMPLE 227 2-Benzoyl-6-chloro-3- (3-fluoro-5-trifluoro-methylbenzamido) indole. MS m / z: 459 r (M-H) 1 EXAMPLE 228 2-Benzoyl-6-chloro-3- (2-fluoro-3-trifluoromethylbenzamido) indole. MS m / z: 459 [(M-H)] EXAMPLE 229 2-Benzoyl-6-chloro-3- [2,4-di (trifluoromethyl) -benzamido-indole. HPLC [Column: SHISEIDO CAPCELLPAK Cl UG120. 150 x 2.0 mm: Eluvente: MeCN: CH3CO2NH4 0.01 M = 50 / 50-90 / 10: Tret. = 6.30 min EXAMPLE 230 2-Benzoyl-6-chloro-3- (4-fluoro-2-trifluoromethylbenzamido) indole, MS m / z: 459 f (M-H) 1 EXAMPLE 231-Benzoyl-6-chloro-3- (3,4,5-trifluorobenzamido) indole. MS m / z: 428 f (M-H) 1 EXAMPLE 232 2-Benzoyl-6-chloro-3- (octafluorovalerylamine) -indole, MS m / z: 497 T (M-H) 1 EXAMPLE 233 2-Benzoyl-6-chloro-3-r (2-chlorophenyl) acetylamino-indole, HPLC f Column: SHISEIDO CAPCELLPAK Cl UG120. 150 x 2.0 mm: Eluvente: MeCN: CH3CO2NH 0.01 M = 50 / 50-90 / 101: Tret. = 6.03 min EXAMPLE 234 10 2-Benzoyl-6-chloro-3- (4-fluoro-3-trifluoromethylbenzamido) indole, MS m / z: 459 f (M-H) 1 EXAMPLE 235 2-Benzoyl-6-chloro-3- (3,5-dimethoxylbenzamido) indole. MS m / z: 433 i.M-H) 1 EXAMPLE 236 • 2-Benzoyl-6-chloro-3- (2,4-difluorobenzamido) indole. HPLC TColumn: SHISEIDO CAPCELLPAK Cl UG120. 150 x 2.0 mm: Eluvente: MeCN: CH3CO2NH4 0.01 M = 50 / 50-90 / 101: Tret. = 5.55 min. EXAMPLE 237 2-Benzoyl-6-chloro-3- (2-methylbutyrylamino) indole. MS m / z: 353 f (M-H) 1 EXAMPLE 239 2-Benzoyl-6-chloro-3- (4-decylbenzoylamino) indole. MS m / z: 513 f (M-H) 1 EXAMPLE 240 2-Benzoyl-6-chloro-3- (neodecanoylamino) indole. MS m / z: 423 f (M-H) 1 EXAMPLE 241 2-Benzoyl-6-chloro-3- (4-methylvalerylamino) dol. MS m / z: 367 T (M-H) 1 EXAMPLE 242-Benzoyl-6-chloro-3- (4-methyl-4-nitrohexanoylamino) ethylene. MS m / z: 426 f (M- m EXAMPLE 243 2-Benzoyl-6-chloro-3- (trichloroacryloylamino) indole. HPLC rColumn: SHISEIDO CAPCELLPAK Cl UG120. 150 x 2.0 mm; Eluvente: MeCN: CH3CO2NH_, 0.01M = 50 / 5-90 / 101: Tret. = 5.74 min EXAMPLE 244 2-Benzoyl-6-chloro-3- (2,4,6-trifluorobenzamido) indole. MS m / z: 427 Í (M-H) 1 EXAMPLE 245 2-Benzoyl-6-chloro-3-f3- (2-chloro-6-fluorophenyl) -5-methylisoxazole-4-carboxamidolindole, MS m / z: 506 I? M-H) 1 EXAMPLE 246 2-Benzoyl-6-chloro-3- (2-fluoro-5-trifluoromethylbenzamido) indole. EM m / z: • 10 459 f (M-H) 1 EXAMPLE 247 2-Benzoyl-6-chloro-3- (5-nitro-2-furoylamino) indole. MS m / z: 408 I? M-H) 1 EXAMPLE 248 2-Benzoyl-6-chloro-3- (2-phenoxybutyrlamino) indole. MS m / z: 431 Í (M-H) 1 • EXAMPLE 249 2-Benzoyl-6-chloro-3- (6-chlorohexanoylamino) -indole, MS m / z: 401 f (M-H) 1 EXAMPLE 250 2-Benzoyl-6-chloro-3- (2-ethoxy-2-naphthoylamino) indole. MS m / z: 467 i.M-H.I EXAMPLE 251 2-Benzoyl-6-chloro-3- (2-chloronicotinoylamino) indole, MS m / z: 408 T (M-H) 1 EXAMPLE 252 2-Benzoyl-6-chloro-3-r3- (2,6-dichlorophenyl) -5-methylisoxazole-4-carboxamidolindole. MS m / z: 522 I (M-H) 1 EXAMPLE 253 2-Benzoyl-6-chloro-3- (2-fluoro-4-trifluoromethylbenzamido) indole. EM m / z: 459 KM-H? EXAMPLE 254 2-Benzoyl-6-chloro-3- (3-trifluoromethoxybenzamido) indole. EM m / z: 459 M- n EXAMPLE 255 2-Benzoyl-6-chloro-3- (2-methylvalerylamino) indole. MS m / z: 367 I (M-H) 1 EXAMPLE 256 methyl 4-rr (2-benzoyl-6-chloro) indol-3-ill-amino-carboninpentanoate. MS m / z: 411 f (M-H) 1 EXAMPLE 258 2-Benzoyl-6-chloro-3-f3- (2-chlorophenyl) -5-methylisoxazole-4-carboxamido-indol, EXAMPLE 259 2-Benzoyl-6-chloro-3-r.4-chloropheniP acetylaminolindole. MS m / z: 421 I (M-H) 1 EXAMPLE 260 2-Benzoyl-6-chloro-3-r (4-methylphenyl) acetylamino-indole. Em m / z: 401 Í (M-H) 1 EXAMPLE 261 2-Benzoyl-6-chloro-3- (1-methylcyclohexylcarboxamido) indole. MS m / z: 393 G (M-H? EXAMPLE 262 2-Benzoyl-6-chloro-3- (4-bromobutyrylamino) -6-chloroindole. MS m / z: 417 I M- EXAMPLE 263 Methyl 2-methyl (2-benzoyl-6-chloro) indol-3-ylaminocarbonylbutanoate. MS m / z: 383 T (M-H 1 EXAMPLE 264 2-Benzoyl-6-chloro-3- (3,4,5-trimethoxybenzamido) indole MS m / z: 463 T (M-H) 1 EXAMPLE 265 methyl 4-IT (2-benzoyl-6-chloro) indol-3-aminocarbonyl-1-pentanoate. MS m / z: 397 f (M-H) 1 EXAMPLE 266 2-Benzoyl-6-chloro-3- (2,3,4-trifluorobenzamido) indole. MS m / z: 427 f (M-H) 1 • 10 EXAMPLE 267 2-Benzoyl-6-chloro-3- (4-chloro-3-nitrobenzamido) indole. MS m / z: 452 I (M-H) 1 EXAMPLE 268 2-Benzoyl-6-chloro-3- (4-propylbenzamido) dol. MS m / z: 415 T (M-H) 1 EXAMPLE 269 3- (2-Acetoxy-2-phenylacetylamino) -2-benzoyl-6-chloroindole, Em m / z: 445 \ (M-H? 20 EXAMPLE 270 2-Benzoyl-6-chloro-3- (2.3- dichloroproponylamino) indole MS m / z: 393 T (MH) 1 EXAMPLE 271 2-Benzoyl-6-chloro-3- (5-bromovalerylamino) indole MS m / z: 431 T (MH) 1 . EXAMPLE 272 5 2-Benzoyl-6-chloro-3-r (4-methoxyphenyl) acetylamino-indole. MS m / z: 417 f (M-H) 1 EXAMPLE 273 2-Benzoyl-6-chloro-3- (benzyloxy-acetylamino) -6-chloroindole. MS m / z: 417 f (M- • 10 EXAMPLE 274 2-Benzoyl-6-chloro-3- (2-thiopheneacetylamino) indole. MS m / z: 393. (M-H) 1 EXAMPLE 275 2-Benzoyl-6-chloro-3- (2,3-difluorobenzamido) indole. MS m / z: 409 KM-HVI • EXAMPLE 276 2-Benzoyl-6-chloro-3- (2,5-difluorobenzamido) indole. MS m / z: 409 I (M-H) 1 EXAMPLE 277 2-Benzoyl-3- (6-bromohexanoylamino) -6-chloroindole. MS m / z: 445 I (M-H) 1 EXAMPLE 278 2-Benzoyl-6-chloro-3- (3,4-dimethoxybenzamido) indole. HPLC [Column: SHISEIDO CAPCELLPAK Cl UG120. 150 x 2.0 mm: Eluvente: MeCN: CH3CO? NH_? 0.01 M = 50 / 5P-90/101: Tret. = 4.60 min 5 EXAMPLE 279 2-Benzoyl-6-chloro-3- (cyclobutylcaboxamido) -indole, MS m / z: 351 I (M-H) 1 EXAMPLE 280 10 2-Benzoyl-6-chloro-3- (3-methoxybenzamido) indole. MS m / z: 403 T (M-H) 1 EXAMPLE 281 2-Benzoyl-6-chloro-3- (2,6-difluorobenzamido) indole. MS m / z: 409 f (M-H) 1 EXAMPLE 282 2-Benzoyl-3- (3-bromopropionylamino) -6-chloroindole, MS m / z: 403 I (M-H) 1 • EXAMPLE 283 2-Benzoyl-6-chloro-3- (2,3,6-trifluorobenzamido indole MS m / z: 427 f (M-H) 1 EXAMPLE 284 2-Benzoyl-6-chloro-3-r3- (dichloromethyl) benzamido1indole. MS m / z: 455 T (M-H) 1 EXAMPLE 285 2-Benzoyl-6-chloro-3-r3- (cyclopentyl) propion.lamino) 1indol, MS m / z: 433 T (M-HH) EXAMPLE 286 2-Benzoyl-6-chloro-3- (4-butylbenzamido) -6-chloroindole. MS m / z: 439 T (M-H) 1 EXAMPLE 287 3- (2-Acetoxybenzamido) -2-benzoyl-6-chloroindole, MS m / z: 431 T (MH) 1 10 EXAMPLE 288 2-Benzoyl-6-chloro-3-r3- (chloromethyl-p-benzamidolindole, EM m / z: 421 T (MH) 1 EXAMPLE 289 2-Benzoyl-6-chloro-3-r2-nitrobenzamido1indol. MS m / z: 418 T (M-H) 1 EXAMPLE 290 2-Benzoyl-6-chloro-3- (3,5-difluorobenzamido) indole. MS m / z: 409 T (M-H) 1 EXAMPLE 291 2-Benzoyl-6-chloro-3-r (3,5-dimethoxyphenyl) -acetylamino-indole. MS m / z: 447 HM-H? EXAMPLE 292 2-Benzoyl-6-chloro-3- (diphenylacetylamino) indole. MS m / z: 463 L? M-HVI EXAMPLE 293 5-Benzoyl-6-chloro-3-y3,5-d, (trifluoromethyl) -benzamido-1-indole. MS m / z: 509 KM-H? EXAMPLE 294 2-Benzoyl-6-chloro-3- (2,4-dichloro-5-fluorobenzamido) indole, MS m / z: 459 9 10 G (M-H) I EXAMPLE 295 2-Benzoyl-6-chloro-3-r (3-methoxyphenyl) acetylamino-indole. MS m / z: 417 T (M-H) 1 EXAMPLE 296 2-Benzoyl-6-chloro-3- (perfluorooctanoylamino) indole. MS m / z: 665 T (M-H) 1 EXAMPLE 297 2-Benzoyl-6-chloro-3- (2-chloro-2,2-diphenyl-acetylamino) indole. HPLC 20 ÍColumn: SHISEIDO CAPCELLPAK Cl UG120. 150 x 2.0 mm; Eluvente: MeCn: CH3CO2NH4 0.01 M = 50 / 50-90 / 101: Tret. = 6.68 min EXAMPLE 298 2-Benzoyl-6-chloro-3- (4-hexylbenzamido) indole. MS m / z: 457 T (M-H) 1 EXAMPLE 299 5 2-Benzoyl-6-chloro-3- (4-heptyloxybenzamido) indole. MS m / z: 487 I (M-H) 1 EXAMPLE 300 2-Benzoyl-6-chloro-3-y2,5-di (trifluoromethyl) -benzamido-indole, MS m / z: 509 G (MH? 10 EXAMPLE 301 4-rf (2-benzoyl-6-chloro) methyl indole-3-in-aminocarbonyl heptanoate MS m / z: 439 T (MH) 1 EXAMPLE 302 2-Benzoyl-6-chloro-3- (4-ethylbenzamido) indole. MS m / z: 401 f (M-H 1 f EXAMPLE 303 2-Benzoyl-6-chloro-3- (2.3.4.5-tetrafluorobenzamido) indole. MS m / z: 445 T (M- 20 HH EXAMPLE 305 2-Benzoyl-6-chloro-3- (cyclopentylcarboxamido) indole. MS m / z: 365 I (M-H) 1 EXAMPLE 306 2-Benzoyl-6-chloro-3- (3,4-difluorobenzamido) dol. MS m / z: 409 I (M-H) 1 • 10 EXAMPLE 307 2-Benzoyl-6-chloro-3- (4-trifluoromethoxybenzamido) indole, MS m / z: 457 f (M-HH EXAMPLE 308 2-Benzoyl-6-chloro-3- (2,4,5-trifluorobenzamido) dol. MS m / z: 427 T (M-H) 1 • EXAMPLE 309 2-Benzoyl-3- (4-butoxybenzamido) -6-chloroindole. MS m / z: 445 KM-H.I 20 EXAMPLE 310 2-Benzoyl-6-chloro-3-r (2,5-dimethoxyphenyl) -acetylamino-indole. MS m / z: 447 G (M-H? ! W * OS ^ ® ^ sa ^ EXAMPLE 311 3-f-acetoxy-acetylamino-1-2-benzoyl-6-chloroindole. MS m / z: 369 I (M-H) 1 EXAMPLE 312 2-Benzoyl-6-chloro-3- (4-pentylbenzamido) indole. MS m / z: 443 I (M-H) 1 EXAMPLE 313 2-Benzoyl-6-chloro-3- (4-vodobenzamido) indole. MS m / z: 499 T (M-H) 1 EXAMPLE 314 2-Benzoyl-6-chloro-3- (4-hexyloxybenzamido) indole. MS m / z: 473 T (M-H) 1 EXAMPLE 315-Benzoyl-6-chloro-3- (cyclohex-3-enylcarboxamido) idol. MS m / z: 377 UM- HH EXAMPLE 316 (R) -2-Benzoyl-6-chloro-3- (alpha-methoxy-alpha-trifluoromethylphenylacetylamino) ethylene. MS m / z: 485 T (M-H) 1 EXAMPLE 317 (S) -2-Benzoyl-6-chloro-3- (alpha-methoxy-alpha-trifluoromethylphenylacetylamino) indole. MS m / z: 485 KM-Hn EXAMPLE 318 2-Benzoyl-6-chloro-3- (2-fluorobenzamido) indole. MS m / z: 391 I (M-H) 1 EXAMPLE 319 2-Benzoyl-6-chloro-3-r (r) - (-) phenyl-quinolininol. HPLC iColumn: SHISEIDO CAPCELLPAK Cl UG120. 150 x 2.0 mm; Eluvente: MeCN: CH3CO? NH_t 0.01 M = 50 / 50-90 / 101: Tret. = 4.27 min EXAMPLE 320 2-Benzoyl-6-chloro-3- (4-ethoxybenzamido) indole. MS m / z: 417 (M-H, 1 EXAMPLE 321 2-Benzoyl-6-chloro-3- (3-chlorobenzamido) indole. MS m / z: 407 KM-HH EXAMPLE 322 (2-Benzoyl-6-chloroindol-3-ylamino) -n, n-diethylbenzenesulfonamide. MS m / z: 536 f (M-H) 1 EXAMPLE 323 2-Benzoyl-6-chloro-3-r.1-naphtolpaacetylamino1ndol, MS m / z: 437 KM-HI EXAMPLE 324 2-Benzoyl-6-chloro-3- (2-fluoro-6-) trifluorobenzamido) indole, HPLC FColumna: SHISEIDO CAPCELLPAK Cl UG120. 150 x 2.0 mm; Eluvente: MeCN: CH ^ CO2NH_? 0.01 M = 50 / 50-90 / 101: Tret. = 5.71 min.

EXAMPLE 325 Methyl 2-IT (2-benzoyl-6-chloro) indol-3-n-aminocarbonyl acetate. EM m / z: 369 KM-HH EXAMPLE 326-Benzoyl-6-chloro-3- (2-trifluoromethoxybenzamido) indole. EM m / z: 457 UW? - HH EXAMPLE 327 2-Benzoyl-6-chloro-3-r-oxazole-5-carboxamido1indole, MS m / z: 364 I (M-H) 1 EXAMPLE 328-Benzoyl-6-chloro-3- (2-chloro-6-fluorobenzamido) indole. EM m / z: 425 KM-HV 1 EXAMPLE 329 2-Benzoyl-3-r5-tert-butyl-2-methylpyrazole-3-carboxamido-1-6-chloroindole. MS m / z: 433 r (M-H) 1 EXAMPLE 330 2-Benzoyl-6-chloro-3- (2,3-dimethylbenzamido) indole. MS m / z: 401 MM-H.I EXAMPLE 331 5 2-Benzoyl-6-chloro-3- (2-chloro-4-fluorobenzamido) indole, MS m / z: 425 T (MH) "1 EXAMPLE 332 2-Benzoyl-3-r4-bromo-2 -ethyl-5-methylpyrazole-3-carboxamido-1-6-chloroindole, MS m / z: 483 ..M-HH • 10 EXAMPLE 333 2-Benzoyl-6-chloro-3-r4-methyl-1, 2.3- thiadiazole-5-carboxamido1indole, MS m / z: 395 T (MH) 1 EXAMPLE 334 2-Benzoyl-6-chloro-3-f5-methyl-3-phenylsoxazole-4-carboxamido-indole, MS m / z: 454 f (M-H) 1 EXAMPLE 335 20 2-Benzoyl-6-chloro-3- (6-c.loronicotinoylamino) indole MS m / z: 408 T (MH) 1 EXAMPLE 336 2-Benzoyl-3-r 2 -benzyl-5-tert-butylpyrazole- 3-carboxamido-1-6-chloroindole, MS m / z: 509 f (MH) 1 EXAMPLE 337 2-Benzoyl-6-chloro-3- (2-chloro-3-methoxy-4-thiophenecarboxamido). indole TLC TMerk Kieselqel 60. Art 1.05719: AcOEt-PhMe (1: 8) 1 Rf 0.55 EXAMPLE 338 # 10 2-Benzoyl-6-chloro-3- (3-chloro-4-methanesulfonyl-2-thiophenecarboxamido) indole. HPLC TC column: SHISEIDO CAPCELLPAK Cl UG120. 150 x 2.0 mm: Eluvente: MecN: CH3CO2NH_? 0.01 M 50 / 50-90 / 101: Tret. = 4.67 min EXAMPLE 339 15 2-Benzoyl-6-chloro-3-r3-trifluoromethyl-2- (4-chloro-phenyl) pyrazole-4-carboxamidolindole, HPLC rColumn: SHISEIDO CAPCELLPAK Cl UG120. 150 x 2.0 mm: Eluvente: MeCN: CH3CO? NH_, 0.01 M = 50 / 50-90 / 101: Tret. = 6.28 min EXAMPLE 340 2-Benzoyl-6-chloro-3- [5-methylisoxazole-3-carboxamido-indol, MS m / z: 378 f (MH) 1 EXAMPLE 341 2-Benzoyl-6-chloro-3- (3- chloro-2-thiophenecarboxamido) indole, MS m / z: 413 f (M-MH EXAMPLE 342 2-Benzoyl-6-chloro-3- (2,2,3,3-tetrafluoropropionylamino) indole, MS m / z: 397 HM-H? EXAMPLE 343"" 10 2-Benzoyl-6-chloro-3- (3,4-dichloro-2.2.3.4.4-pentafluorobutyrylamino) indole. MS m / z: 497 KM-HH EXAMPLE 344 2-Benzoyl-6-chloro-3- (9h-hexadecafluorononanoylamino) ndol. HPLC 15 rColumn: SHISEIDO CAPCELLPAK Cl UG120. 150 x 2.0 mm: Eluvente: MeCN: CH3CO? NH_, 0.01 M = 50 / 50-90 / 101: Tret. = 7.18 min EXAMPLE 345 2-Benzoyl-6-chloro-3- (3-chloro-2,2,3,3-tetrafluoropropionylamino) indole. MS 20 m / z: 431 f (M-H) 1 EXAMPLE 346-Benzoyl-6-chloro-3-r2- (4-chlorophenyl) -3-propylpyrazole-4-carboxamido1indole. MS m / z: 515 f.M-HVI EXAMPLE 347-Benzoyl-6-chloro-3- (trans-3-trifluoromethylcinnamoylamino) MS m / z: 467 I (M- HH EXAMPLE 348 2-Benzoyl-6-chloro-3- (4-pentoxybenzamido) indole. HPLC fColumn: SHISEIDO CAPCELLPAK Cl UG120. 150 x 20. mm; Eluvente: MeCN: CHr.CO, .NH_. 0.01 M = 50 / 50-90 / 101: Tret. = 5.75 min EXAMPLE 349 2-Benzoyl-6-chloro-3- (4-heptylbenzamido) indole. MS m / z: 471 T (M-H) 1 EXAMPLE 350 2-Benzoyl-6-chloro-3- (2,5-dichlorothiophen-3-carboxamido) -indole. HPLC rColumn: SHISEIDO CAPCELLPAK Cl UG120. 150 x 2.0 mm: Eluvente: MeCN: CH3C02NH_, 0.01 M = 50 / 50-90 / 101: Tret. = 6.11 min EXAMPLE 351 2-Benzoyl-6-chloro-3- (3-cyanobenzamido) indole. MS m / z: 398 KM-HVI EXAMPLE 352 2-Benzoyl-6-chloro-3- (vodoacetylamino) indole. HPLC iColumn: SHISEIDO CAPCELLPAK Cl UG120. 150 x 2.0 mm: Eluvente: MeCN: CH3CO2NH_t • 0.01 M = 50 / 50-90 / 101: Tret. = 4.39 min EXAMPLE 353 2-Benzoyl-6-chloro-3-r5.6-dichloronicotinoylamino-indole. MS m / z: 442 I (M-H) 1 EXAMPLE 354 • 10 3-f f1 (2-Benzoyl-6-chloro) indole-3-inaminocarbonyl propionic acid A mixture of 2-benzoyl-6-chloro-3 - [(3-ethoxycarbonyl) -propynylamino) indole (Example 56) (500 mg, 1.25 mmol), 2N potassium hydroxide (5 ml) and ethanol (15 ml) was stirred at room temperature for 2 hours. The The mixture was concentrated and 2N-charged HCl (10 ml) was added, and then extracted with diethyl ether (80 ml x 2), dried (MgSO) and concentrated to give a pale yellow solid. Recrystallization from ethyl acetate / hexane gave 150 mg (32%) of the title compound as a pale yellow solid, mp: 204-207 ° C-NMR (CDCl 3) d: 9.94 (1 H, s), 9.81 (1 H, sa), 8.12 (1H, d, J = 8.8 Hz), 7.88-7.78 (2H, m), 7.67-7.48 (3H, m), 7.36 (1H, d, J = 1.8 Hz), 7.04 (1H, dd, J = 1.8, 8.8 Hz), 2.72 (4H, s).

EXAMPLE 355 2-Benzoyl-6-chloro-3- (3-oxobutyrylamino) indole A mixture of 3-amino-2-benzoyl-6-chloroindole (Example 1) (850 mg, 4.07 mmol) and tert-butyl acetoacetate (1.3 mL, 8.15 mmol) in xylene (10 mL) was heated to 120 ° C. for 5 h. The mixture was concentrated and purified by flash column chromatography eluting with hexane / ethyl acetate (2/1) to give a yellow amorphous solid. Recrystallization from ethyl acetate / hexane gave 450 mg (31%) of the title compound as a pale yellow solid, mp: 170-173 ° C-NMR (CDCl 3) d: 10.22 (1 H, sa), 8.47 (1 H, sa), 8.01 (1 H, d, J = 8.8 Hz), 7.83-7.77 (2 H, m), 7.65-7.50 (3 H, m), 7.32 (1 H, d, J = 1.5 Hz) , 7.11 (1 H, dd, J = 1.5, 8.8 Hz), 3.56 (2H, s), 2.32 (3H, s).

EXAMPLE 356 2-Benzoyl-6-chloro-3- (3-hydroxybutyryl-amino) indole Step 1. 3-Benzoyl-3- (3-benzyloxybutylarylamino) -6-chloroindole The title compound was prepared according to the procedure described in Example 19 using 3-amino-2-benzoyl-6-chloroindole (Example 1) and 3-benzyloxybutyl chloride or (Eberlein, TH et al., J.

Org. Chem. 1992, 57, 3479). -NRM (CDCI3) d: 10.22 (1 H, s a), 8.47 (1 H, s a), 8.01 (1 H, d, J = 8.8 Hz), 7.83-7.77 (2H, m), 7.65-7.50 (3H, n), 7.50-7.15 (6H, m), 7.11 (1H, dd, J = 1.5, 8.8 Hz), 4.60-4.45 (2H, m), 4.02-3! 97 (1 H, m), 2.70-2.50 (2H, m), 1.40 (3H, d, J = 6.2 Hz).

Step 2. 2-Benzoyl-6-chloro-3- (3-hydroxybutyrylamino) -dol A mixture of 2-benzoyl-3- (3-benzyloxybutyrylamino) -6-chloroandol (Step 1) (2.3 g, 5.1 mmol) and Pd-C 10% (0.2 g) in ethyl acetate (50 ml) was stirred at room temperature for 24 h under nitrogen atmosphere. The mixture was filtered through a pad of Celite and the filtrate was concentrated. Purification by flash column chromatography eluting with hexane / ethyl acetate (1/1) gave a pale yellow amorphous solid. Recrystallization from ethyl acetate / hexane gave 290 mg (16%) of the title compound as a pale yellow solid, mp 159-162 ° C-NMR (CDCl 3) d: 9.95 (1 H, s), 8.70 (1 H, sa), 8.16 (1 H, d, J = 8.8 Hz), 7.81-7.77 (2H, m), 7.68-7.51 (3H, m), 7.30 (1 H, d, J = 1.5 Hz), 7.11 (1 H, dd, J = 1.5, 8.8 Hz), 4.29 (1 H, sa), 3.43 (1 H, sa), 2.62-2.55 (2 H, m), 1.28 (3 H, d, J = 6.2 Hz) .

EXAMPLE 357 6-Chloro-2- (3-furoyl) -3- (isovalerylamino) indole The title compound was prepared according to the procedure described in Example 19 from 3-amino-6-chloro-2- (3-furoyl) indole (Example 79) and isovaleryl chloride. mp: 202-203 ° C (recrystallized from ethyl acetate) -NMR (CDCl 3) d: 10.10 (1 H, sa), 8.28 (1 H, d, J = 8.8 Hz), 8.23 (1 H, sa), 8.11 (1 H, dd, J = 0J, 1.5 Hz), 7.59 (1 H, dd, J = 1.5, 1.8 Hz), 7.31 (1 H, d, J = 1.8 Hz), 7.10 (1 H, dd, J = 1.8, 8.8 Hz), 6.89 (1 H, dd, J = 0J, 1.8 Hz), 2.39-2.22 (3H, m), 1.06 (6H, d, J = 6.6 Hz).

EXAMPLE 358 6-Chloro-2- (4-chloropyridine-2-carboni) -3- (propionylamino) indole The title compound was prepared according to the preparation described in Example 19 from 3-amino-6-chloro-2- (4-chloropyridin-2-carbonyl) indole (example 68) and propionyl chloride. mp: 188-190 ° C (recrystallized from ethyl acetate) - NMR (CDCl 3) d: 11.68 (1 H, br), 10.88 (1 H, br), 8.70 (1 H, d, J = 5.4 Hz), 8.54 (1 H, d, J = 9.1 Hz), 8.37 (1 H, d, J = 2.0 Hz), 7.58 (1 H, dd, J = 2.1, 5.3 Hz), 7.40 (1 H, d, J = 2.0 Hz), 7.06 (1 H, dd, J = 1.1, 9.1 Hz), 2.63 (2H, q, J = 7.6 Hz), 1.37 (3H, t, J = 7.6 Hz).

EXAMPLE 359 6-Chloro-2- (4-chloropyridine-2-carbonyl) -3- (isovalerylamino) ndol The title compound was prepared according to the procedure described in Example 19 from 3-amino-6-chloro-2- (4-chloropyridine-2-carbonyl) indole (Example 68) and isovaleryl chloride. mp .: 183-184 ° C (recrystallized from ethyl acetate) -NMR (DMSO-d6) d; 11.67 (1 H, sa), 10.08 (1 H, sa), 8.69 (1 H, d J = 5.3 Hz), 8.52 (1 H, d, J = 9.2 Hz), 8.37 (1 H, d, J = 2.1 Hz), 7.57 (1 H, dd, J = 2.0, 5.3 Hz), 7.39 (1 H, d J = 2.0 Hz), 7.06 (1 H, dd J = 2.0, 9.6 Hz), 2.46 -2.30 (3 H, m), 1.09 (1 H, d.J = 6.4 Hz).

EXAMPLE 360 3- (2-Acetoxybutylamino) -6-chloro-2- (4-chloropyridine-2-carbonylPindole) The title compound was prepared according to the example described in Example 19 using 3-amino-6-chloro-2- (4-chloropyridin-2-carbonyl) indole (Example 68) and 2-acetoxyisobutyryl chloride. mp: 228-229 ° C (recrystallized from ethyl acetate)) IR (KBr) v: 3500, 3250, 1740, 1710, 1620, 1600, 1570, 1540, 1480, 1350, 1230, 1180, 1150, 740 cm " 1.-NMR (DMSO-de) d: 12.07 (1 H, sa), 10.71 (1 H sa), 8.80 (1 H, d J = 5.3 Hz), 8.15 (1 H, d, J = 2.1 Hz ), 8.04 (1 H, dd, J = 8.8, 3.7 Hz), 7.90 (1 H, dd, J = 5.4, 1.9 Hz), 7.65 (1 H, d J = 2.0 Hz), 7.09 (1 H, dd J = 9.0, 1.4 Hz), 2.14 (3 H, s), 1.55 (6 H, s).

EXAMPLE 361 6-Chloro-2- (4-chloropyrdin-2-carboniP-3- (2-hydroxyisobutyrylamino) indole To a suspension of 3- (2-acetoxy-isobutyrylamino) -6-chloro-2- (4-chloropyridine-2-carbonyl) indole (Example 360, 251.4 mg, 0.5789 mmol) in methanol (8 ml) and DMSO (20 ml) was added potassium carbonate (45.0 mg, 0.3259 mmol) in water (1 ml) at room temperature. After stirring for 30 h, the mixture was diluted with diethyl ether (150 ml), and washed with water (25 ml x 3), brine (25 ml) and dried (MgSO 4). Removal of the solvent gave a crystalline residue which was recrystallized from ethyl acetate to give 103.9 mg (45.8%) of the title compound. mp: 207-208 ° C (recrystallized from ethyl acetate) IR (KBr) v: 3346, 3285, 1665, 1626, 1570, 1531, 1483, 1348, 1232, 741 cm "1-NMR (DMSOde) d: 11.75 (1 H, sa), 11.69 (1 H sa), 8.68 (1 H, dd, J = 5.3 and 0.5 Hz), 8.56 (1 H, d, J = 9.1 Hz), 8.40 (1 H, dd, J = 2.1, 0.5 Hz), 7.56 (1 H, dd, J = 5.3, 2.1 Hz), 7.40 • 10 (1 H, dd J = 1.9, 0.6 Hz), 7.06 (1 H, dd J = 9.1, 1.8 Hz), 2 J7 (1 H, s), 1.56 (6 H, s).

EXAMPLE 362 3-r (S) -2-Acehoxypropionyl-1-amino-1-6-chloro-2- (4-chloro-pyridin-2- 15-carboni-Pindol • The title compound was prepared according to the procedure described in Example 19 using 3-amino-6-chloro-2- (4-chloropyridine-2-carbonyl) dol (Example 68) and (S) chloride. ) - (-) - 2- 20 acetoxypropionyl. mp: 236-238 ° C (recrystallized from ethyl acetate) IR (KBr) v: 3287, 1738, 1693, 1624, 1585, 1570, 1545, 1489, 1236, 1188, 739 cm "1. - NMR (DMSO- de) d: 12.09 (1 H, sa), 10.67 (1 H sa), 8.77 (1 H, dd J = 5.5 and 1.8 Hz), 8.10 (1 H, t, J = 1.9 Hz), 7.93 (1 H, dd, J = 9.1, 1.8 Hz), 7.88 (1 H, dt, J = 5.4, 2 3 2. 3 Hz), 7.64 (1 H, dd J = 1.9, Hz), 7.12 (1 H, dt J = 9.1, 2.1 Hz), 5.13 (1 H, q, J = 6.8 Hz), 2.18 (3 H, s), 1.35 (3H, d, J = 6.9 Hz).

EXAMPLE 363 6-Chloro-2- (4-chloropyridine-2-carbonyl) -3-rr (s) -2-hydroxypropioninamino-indole To a suspension of 3 - [(S) -2-acetoxipropionylamino] -6-chloro-2- (4-chloropyridine-2-carbonyl) indole (Example 362, 316.7 mg, 0.7536 mmol) in DMSO (10 mL) was added potassium carbonate (104.2 mg, 0.7536 mmol) in water (1 mL) at room temperature. After stirring for 30 h the mixture was diluted with diethyl ether (200 ml) and then washed with water (50 ml × 3), brine (50 ml) and dried (MgSO4). Removal of the solvent gave a crystalline residue which was recrystallized from ethyl acetate to provide 213.0 mg (74.7%) of the title compound, mp: 244-246 ° C (recrystallized from ethyl acetate) IR (KBr) v: 3483, 3288 1690, 1570, 1553, 1481, 1348, 1240, 1186, 737 cm "1 H NMR (DMSO-d6) d: 12.07 (1 H, sa), 11.43 (1 H sa), 8.82 (1 H, dd. = 5.3 and 0.5 Hz), 8.26 (1 H, d, J = 9.1 Hz), 8.20 (1 H, dd, J = 2.1, 0.5 Hz), 7.91 (1 H, dd, J = 5.4, 2.1 Hz), 7.67 (1 H, dd J = 2.0, 0.5 Hz), 7.07 (1 H, dd J = 8.9, 2.0 Hz), 6.18 (1 H, d, J = 4.9 Hz), 4.23 (1 H, dd, J = 6.8, 4.9 Hz), 1.34 (3 H, d, J = 6.8 Hz).

EXAMPLE 364 3- (N-Acetyl-n-methylamino) -6-chloro-2- (4-chloropyridine-2-carbonyl) indole STEP 1. 6-Chloro-2- (4-chloropyridine-2-carbonyl) -1-ethoxycarbonyl-3- (N-acetyl-N-methylamino) indole To a solution of 3-amino-6-chloro-2- (4-chloropyridin-2-carbonyl) -1-ethoxycarbonylindole step 1 of Example 68, 407 mg, 1.08 mmol) in dichloromethane (10 ml ) pyridine (0.42 ml, 5.38 mmol) and acetyl chloride (0.09 ml, 1.29 mmol) were added at room temperature. After stirring for 1 h, it was added to the mixture in methanol (1 ml) at room temperature. The mixture was concentrated and the residue was diluted with ethyl acetate (100 ml). The resulting mixture was washed with 2N aqueous HCl (50 ml x 2) and saturated sodium bicarbonate in water (50 ml) and dried (Na2SO). Removal of the solvent gave a crystalline residue (413 mg). The residue was dissolved in DMF (5 ml) and then sodium hydride (60% in oil) (43 mg, 1.08 mmol) was added at room temperature. After stirring for 0.5 h Mel (0.07 mL, 1.08 mmol) was added and the mixture was stirred for an additional 1 h. The mixture was diluted with diethyl ether (100 ml), washed with water (50 ml x 2) and brine (50 ml), and dried (MgSO). Removal of the solvent gave an oily residue which was purified by flash column chromatography eluting with ethyl acetate / hexane (1: 3) to give 111 mg (26%) of the title compound as an oil. NMR (CDCL3) d: 8.46 (1 H, dd J = 5.1 and 0.6 Hz), 8.25 (1 H, d, J = 1.8, 0.6 Hz), 8.18 (1 H, dd, J = 2.1, 0.6 Hz) , 7.48 (1 H, dd, J = 5.1, 2.1 Hz), 7.44 (1 H, d J = OJ Hz), 7.39 (1 H, dj = 1.8 Hz), 4.21 (2 H, q, J = 7.2 Hz), 3.19 (3H, s), 1.91 (3 H, s), 1.14 (3 H, t, J = 7.2 Hz).

Step 2. 3- (N-Acetyl-N-methylamino) -6-chloro-2- (4-chloropyridine-2-carboniPindol) The title compound was prepared according to the procedure described in step 2 of Example 2 (Method A) using 6-Chloro-2- (4-chloropyridine-2-carbonyl) -1-ethoxycarbonyl-3- (N-acetyl-N-methylamino) dol (step 1). : 236-237 ° C (recrystallized from ethyl acetate) IR (KBr) v: 3250, 1649, 1522, 1375, 1350, 1296, 1238, 1213, 1180, 1055, 1007, 781, 740 cm. "1. DMSO-de) d: 12.37 (1 H, sa), 8J2 (1 H dd, J = 5.3 and 0.5 Hz), 8.10 (1 H, dd J = 2.1 and 0.5 Hz), 7.86 (1 H, dd, J = 5.3, 2.1 Hz), 7.68 (1 H, dd, j = 1.8, 0.5 Hz), 7.62 (1 H, dd, J = 8.6, 0.5 Hz), 7.21 (1 H, dd, J = 8.6, 1.8 Hz), 2.95 (3 H, s), 1.70 (3 H, s).

EXAMPLE 365 6-Chloro-2- (3-chlorobenzoyl) -3- (n-methyl-n-propionylamino) indole Step 1. 6-Chloro-2- (3-chlorobenzoyl) -1-ethoxycarbonyl-3- (propionylamino) indole The title compound was prepared according to the procedure described in step 1 of Example 2 (Method A) from 3-amino-6-chloro-2- (3-chlorobenzoyl) -1- (ethoxycarbonyl) idol (step 1 of Example 30) and propionyl chloride. mp .: 189-191 ° C (recrystallized from ethyl acetate). NMR (DMSO-de) d: 9.14 (1 H, sa), 8.21 (1 H d, J = 1.8 Hz), 7.99 (1 H, d, J = 8.7 Hz), 7.79 (1 H, t, J = 2.0 Hz), 7.58 (1 H, dd, J = 1.5, 1.5, 7.7 Hz), 7.53 (1 H, ddd, J = 1.5, 2.1, 8.7 Hz), 7.39 (1 H, t J = 7.8 Hz) , 7.31 (1 H, dd J = 2.0, 8.7 Hz), 3.99 (2 H, q, J = 7.2 Hz), 2.50 (1 H, q, J = 7.5 Hz), 1.26 (3 H, t, J = 7.5 Hz), 1.02 (3 H, t, J = 7.2 Hz).

Step 6-Chloro-2- (3-chlorobenzo-P-3- (N-methyl-N-propionylamino) indole The title compound was prepared according to the procedure described in Example 146 using 6-chloro-2- ( 3-chlorobenzoyl) -1-ethoxycarbonyl-3- (propionylamino) indole (step 1) .pf: 194-195 ° C (recrystallized from ethyl acetate / hexane). 1 H NMR (CDCl 3) d: 9.10 (1 H, s a), 7. 66-7.41 (6 H, m), 7.22 (1 H, dd J = 1.8 and 8.7 Hz), 3.03 (1 H, s), 2.07 (2 H, dd, J = 7J Hz), 0.99 (3 H , t J = 7J Hz).

EXAMPLE 366 3-Acetylamino-6-chloro-2- (5-pyrimidinylcarbonyl) indole step 1. 5-Bromoacetylpyridine A mixture of 5-bromopyrimidine (2.20 g, 13.85 mmol), (1-ethoxyvinyl) tributyltin (5.00 g, 13.85 mmol) and tetrakis (triphenylphosphine) palladium (1.60 g, 1.38 mmol) in toluene (20 ml) was refluxed for 29 h and then cooled to room temperature. The mixture was filtered through a pad of Celite and the filtrate was concentrated to give an oily residue. The residue was diluted with THF (30 ml) and water (8 ml). N-bromosuccinimide (2.96 g) was added, 16.61 mmol) at 0 ° C. The resulting mixture was stirred at 0 ° C for 0.5 h and concentrated to approximately 10 ml. The residue was diluted with ethyl acetate (200 ml) and washed with water (100 ml x 2), then dried (MgSO). Removal of the solvent gave an oily residue which was purified by flash column chromatography eluting with ethyl acetate / hexane (1: 3) to give 2.60 mg (94%) of the title compound as an oil. NMR? (CDCl 3) d: 9.41 (1 H), 9.29 (2 H s), 4.40 (2 H, s).

Step 2. 3-Amino-6-chloro-1-ethoxycarbonyl-2- (5-pyrimidinylcarboniPindol) The title compound was prepared according to the procedure described in step 2 of Example 1 from 4-chloro -2- (ethoxycarbonylamino) benzonitrile (Example 1, step 1) and 5-bromoacetylpyrimidine (step 1). NMR? (CDCI3) d: 9.29 (1 H, s), 9.03 (2 H, s), 8.02 (1 H , d.J = 1.6 Hz), 7.57 (1 H, d, J = 8.4 Hz), 7.35 (1 H, dd, J = 1.6, 8.4 Hz), 6.13 (2 H, sa), 4.01 (2 H, q, J = 7.1 Hz), 1.02 (3 H, t, J = 7.1 Hz).

Step 3-Acetylamine-6-chloro-1-ethoxycarbonyl-2- (5-pyrimidinylcarboniPindol) The title compound was prepared according to the procedure described in step 2 of Example 2 (Method A) using 3-amino -6-chloro-1-ethoxycarbonyl-2- (5-pyrimidinylcarbonyl) indole (step 2) and acetyl chloride, NMR (CDCl 3) d: 9.34 (1 H, s), 9.23 (1 H, sa), 9.07 (2 H, s), 7.96 (1 H, d, J = 1.6 Hz), 7J2 (1 H, d, J = 6.7), 7.23 (1 H, dd, J = 1.8, 8J Hz), 4.21 ( 2 H, q, j = 7.1 Hz), 2.25 (3 H, s), 1.23 (3 H, t, J = 7.1 Hz).

Step 4. 3-Acetylamino-6-chloro-1-ethoxycarbonyl-2- (5-pyrimidinylcarboniPindol) The title compound was prepared according to the procedure described in step 2 of Example 2 (Method A) from 3 -acetylamino-6-chloro-1-ethoxycarbonyl-2- (5-pyrimidinylcarbonyl) idol (step 3), mp: 214-215 ° C (recrystallized from ethyl acetate) 1 H NMR (DMSO-d6) ) d: 12.00 (1 H, sa), 10.00 (1 H, sa), 9.35 (1H, s), 8.99 (2 H, s), 7.67 (1 H, d, J = 9.2 Hz), 7.48 (1 H, s), 7.15 (1 H, d, J = 8.6 Hz), 1.65 (3 H, s).

EXAMPLE 367 3-Amino-6-chloro-2- (3-metipyridin-2 -carboniPindol Step 1. 2-Bromoacetyl-3-methypyridine The title compound was prepared according to the procedure described in step 1 of Example 366 using 2-bromo-3-methylpyridine. NMR (CDCU) d: 8.51 (1 H, da, J = 4.0 Hz), 7.63 (1 H, da, J = 7.7 Hz), 7.38 (1 H, dd J = 4.4, 7.7 Hz), 4.88 (2 H, s), 2.62 (3 H, s).

Step 2. 3-Amino-6-chloro-1-ethoxycarbonyl-2- (3-methylpyridin-2-carboniPindol) The title compound was prepared according to the procedure described in step 2 of Example 1 from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (Example 1, step 1) and 2-bromoacetyl-3-methylpyridine (step 1). RMN? (CDCI3) d: 8.36 ( 1 H, dd, J = 1.1, 4.8 Hz), 8.14 (1 H, d, J = 1.8 Hz), 7.64 (1 H, ddd, J = 0.7, 1.5, 7.0 Hz), 7.51 (1 H, dd, J = 0.7, 8.4 Hz), 7.24 (1 H, d, J = 1.8, 8.8 Hz), 7.22 (1 H, d, J = 7 J Hz), 6.05 (2 H, s), 3 J8 -i-Lßßt *! - *? * - a (2 H, q, J = 7.3 Hz), 2.63 (3 H, s), 1.01 (3 H, t, J = 7.3 Hz).

Step 3. 3-Amino-6-chloro-2- (3-methy1-pyridine-2-carbonyl) indole • The title compound was prepared according to the procedure described in step 3 of Example 1 a from 3-amino-6-chloro-1-ethoxycarbonyl-2- (3-methy1pyridine-2-carbonyl) indole (step 2). mp .: 171-172 ° C (recrystallized from ethyl acetyl). NMR (DMSO-de) d: 10.25 (1 H, sa), 8.56 (1 H, d, J = 4.4 Hz), 7.88 (1 H, d J = 8.8 Hz), 7.82 (1 H, d, J = 7 Hz), 7.49 (1 H, dd, J = 4.8, 7.7 Hz), • 10 7.32 (1 H, d, J = 1.8 Hz), 6.91 (1 H, dd, J = 1.8, 8.4 Hz), 2.44 (3 H, s). The signal due to NH2 was not observed.

EXAMPLE 368 3-Acetylamino-6-chloro-2- (3-methylpyridin-2-carbonylPindole) The title compound was prepared according to the procedure described in Example 19 from 3-amino-6-chloro-2- (3-methylpyridine-2-carbonyl) indole (Example 367) and acetyl chloride, mp: 173-175 ° C (recrystallized from ethyl acetate) 20 NMR (DMSO) d: 11.79 (1 H , sa), 9.53 (1 H, sa), 8.46 (1 H, d J = 4.4 Hz), 7.80 (1 H, d, J = 7.0 Hz), 7.61 (1 H, d, J = 8.4 Hz) , 7.47 (1 H, dd, J = 4.4, 7.0 Hz), 7.47 (1 H, d, J = 1.5 Hz), 7.09 (3 H, dd, J = 1.8, 8.8 Hz), 2.37 (3 H, s ), 1.65 (3 H, s).

EXAMPLE 369 6-Chloro-3- (isovalerylamino) -2- (3-methylpyridin-2-carbonylPindole The title compound was prepared in accordance with • procedure described in Example 19 starting from 3-amino-6-chloro- (3-methylpyridine-2-carbonyl) dol (Example 367) and isovaleryl chloride. mp .: 142-144 ° C (recrystallized from ethyl acetate). RM 1 H (DMSO-de) d 11.77 (1 H, sa), 9.50 (1 H, sa), 8.46 (1 H, d, J = 4.8 Hz) 7.79 (1 H, d, J = 7.7 Hz), 7.60 (1 H, D. J = 8.8 Hz), 7.50-7.45 (2 H, m),10 7.09 (1 H, dd, J = 1.8, 8.8 Hz), 2.38 (3 H, s), 1.86-1.74 (3 H, m), 0.81 (6 H, d, J = 6.2 Hz).

EXAMPLE 370 3-Acetylamino-6-chloro-2-F4- (hydroxymethyl) pyridine-2-carbonyl-indole 15 Step 2. Cyano-4- (hydroxyethyl) pyridine To a solution of 4-N-oxide pyridylcarbinol (5.00 g, 39.96 mmol) and TMSCN (8.35 g, 79.92 mmol) in dichloromethane (60 ml) was added dropwise N, N-dimethylcarbamoyl chloride (7.4 ml, 79.92 mmol) to room temperature for 30 min. After stirring for 24 h, potassium carbonate (30 g) in water (100 ml) was carefully added. The organic phase was separated and dried with potassium carbonate. Removal of the solvent gave an oily residue that crystallized from ethanol / hexane to give 3.63 g (68%) of the title compound. NMR? (CDCI3) d: 8.67 (1 H, d, J = 4.9 Hz), 7.74 (1 H, t, J = 0.8 Hz), 7.52 (1 H, dd J = 0.8 Hz), 7.52 (1 H, dd , J = 0.8, 4.9), 4.83 (2 H, s), 2.29 (1 H, sa). • Step 2. 4- (tert-Butylidylmethyloxy) methy1-2-cyanopyridine To a solution of 2-cyano-4-hydroxymethylpyridine (step 1, 3.63 g, 27.06) mmol) in DMF (50 ml) were added imidazole (4.42 g, 64.95 mmol) and TBDMSCI (4.89 g, 32.47 mmol) at room temperature. After stirring for 1 h the mixture was diluted with diethyl ether (300 ml), washed with water • 10 (100 ml x 4) and dried (MgSO 4). Removal of the solvent gave the title compound. NMR (CDCl 3) d: 8.65 (1 H, d, J = 5.1 Hz), 7.68 (1 H, s), 7.46 (1 H, d J = 4.9 Hz), 4 J8 (2 H, s), 0.96 ( 9 H, s), 0.13 (6 H, s).

Step 3.- 2-Acetyl-4 - [(tert-butylmethylsilyloxy) methyl-1-pyridine To a solution of 4- (tert-butylmethylsilyloxymethyl) -2-cyanopyridine (step 2, 6J2 g, 27.06 mmol) in benzene (50 ml) and diethyl ether (50 ml) were • added MeMgl 2M dropwise in diethyl ether (16 ml, 37.89 mmol) at 0 ° C for 30 min. After stirring for 1 h at room temperature saturated ammonium chloride in water (50 ml) was added at 0 ° C. The organic phase was separated, dried (MgSO4) and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate-hexane (1: 12) to afford 1.03 g, (14%) of the title compound. NMR? (CDCI3) d: 8.62 (1 H, d, J = 5.1 Hz), 7.94 (1 H, s), 7.48 (1 H, dd, J = 4.9, 1.8 Hz), 4.78 (2 H, s), 2.71 (3 H, s), 0.94 (9 H, s), 0.11 (6 H, s).

Step 4. 2-Bromoacetyl-4-f (tert-butyldimethylaxylmethylpyridine) To a solution of 2-acetyl-4 - [(tert-butylmethylsilyloxy) methyl) pyridine (step 3, 736 mg, 2 J7 mmol) in THF (15 ml) was added dropwise lithium bis (trimethylsilyl) amide (1.0 M in hexane, 3.3 ml, 3.32 mmol) at -78 ° C for 20 min. After stirring for 1 h, tritylsilyl chloride (OJ ml, 4.16 mmol) was added to the mixture at -78 ° C. The mixture was stirred for an additional 1 h at the same temperature and then allowed to warm to room temperature. After stirring for 1 h, the mixture was poured into saturated ammonium chloride in water (20 ml). The organic phase was separated and dried (MgSO). Removal of the solvent gave an oily residue which was dissolved in THF (10 ml) and water (2 ml). To the mixture was added N-bromosuccinimide (592 mg, 3.32 mmol) at 0 ° C. After stirring for 15 min, the mixture was dissolved with diethyl ether (100 ml), washed with water (50 ml x 2), and dried (MgSO). Removal of the solvent gave an oily residue which was purified by flash chromatography eluting with ethyl acetate / hexane (1:10) to give 1.52 g (quantitative yield) of the title compound. NMR (CDCl 3) d: 8.63 (1 H, d, J = 4.9 Hz), 8.02 (1 H, s), 7.53 (1 H, d J = 5.4 Hz), 4.87 (2 H, s), 4.81 ( 2 H, s), 0.96 (9 H, s), 0.13 (6 H s).

Step 3-Amino-6-c.ooro-1-ethoxycarbonyl-2-f4-y (tert-butyldimethylsilyloxymethylpyridine-2-carbonipindol The title compound was prepared according to the procedure described in step 2 of Example 1 to from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (Example 1, step 1) and 2-bromoacetyl-4 - [(tert-butyldimethylsilyloxy) methyl] pyridine (step 4). NMR (CDCl 3) d : 8.56 (1 H, d, J = 4.9 Hz), 8.22 (1 H, d, J = 2.0 Hz), 7.98 (1 H, sa), 7.51 (1 H, d, J = 8.4 Hz), 7.40 (1 H, br, d, J = 4.9 Hz), 7.23 (1 H, dd, J = 1.8, 8.4 Hz), 6.00 (2 H, sa), 4.83 (2 H, s) 3J8 (2 H, q, J = 7.2 Hz), 0.97 (9 H s), 0.88 (3 H, t, J = 7.2 Hz), 0.14 (6 H, s).

Step 3-Acetylamino-6-chloro-2-f4-f (tert-butyldimethylsilyloxypmetillpyridine-2-carbonylindole) The title compound was prepared according to the procedure described in step 1 of Example 2 (procedure A) from of 3-amino-6-chloro-1-ethoxycarbonyl-2- [4 - [(tert-butyldimethysilyloxy) methyl] pyridine-2-carbonyljindol (step 5) and acetyl chloride. CDCI3) d: 9.49 (1 H, sa), 8.58 (1 H, d, J = 4.9 Hz), 8.19 (1 H, d, J = 1.8 Hz), 8.06 (1 H, s) 7.98 (1 H, d, J = 8.4 Hz), 7.45 (1 H, d, J = 4.9 Hz), 20 7.25 (1 H, dd, j = 1.8, 8.4 Hz), 4.84 (2 H, s) 3.95 (2 H, q , J = 6.9 Hz), 2.24 (3 H s), 1.01-0.93 (3H, m), 0.97 (9 H, s), 0.14 (6 H, s).

Step 7. 3-Acetylamino-6-chloro-2- [4- (hydroxymethiD-pyridine-2-carbonillindole To a solution of 3-acetylamino-6-chloro-2- [4 - [(tert-butyldimet Lysilyloxy) methy1] pyridine-2-carbonyl] indole (step 6, 240 mg, 0.454 mmol) in 5 THF (10 mL) was added 1 M TBAF in THF (OJ mL, 0.681 mmol) at 0 °. C. After stirring for 30 min., Potassium hydroxide (90 mg, 1.36 mmol) in water (2 mL) was added.The mixture was stirred for an additional 1 h at room temperature and concentrated.The residue was diluted with acetate of ethyl (100 ml), and then washed with water (30 ml x 2) and dried (MgSO 4).

• Removal of the solvent gave a crystalline residue which was recrystallized from dichloromethane, yielding 52 mg (33%) of the title compound, mp: 216-218 ° C (recrystallized from dichloromethane). NMR (DMSO-de) d: 12.06 (1 H, sa), 10.49 (1 H, sa), 8J6 (1 H, d, J = 4.9 Hz), 8.07 (1 H, s), 7.86 (1 H, d, J = 8.6 Hz), 7.67-7.64 (2 H, m), 7.07 15 (1 H dd, J = 1.8, 8.7 Hz), 5.62 (1 H, t, J = 5.5 Hz) 4.69 (2 H , d, J = 5.1 Hz), 2.04 (3 H s). • EXAMPLE 371 2- (4-aminopyridine-2-carbonyl) -6-chloro-3- (propionylamino) indole hydrochloride Step 1. 4-IN, Nbys (tert-butoxycarbonyl) amino1-2-chloropyridine A mixture of 4-amino-2-chloropyridine (1.50 g, 11.67 mmol) and di-tert-butyl dicarbonate ( 10 J ml, 46.67 mmol) in dichloromethane (30 ml) was stirred at room temperature for one week. After evaporation the residue was purified by flash column chromatography eluting with ethyl acetate / hexane (1:10) to afford 3.09 g (81%) of the title compound as a solid. 1 H-NMR (CDCl 3) d: 8.38 (1 H, d, J = 5.4 Hz), 7.19 (1 H, d, J = 1.8 Hz), 7.05 (1 H, dd, J = 1.8, 5.4), 1.47 (18 H, s).

Step 2. S-Amino ^ - ^ - fN, N-bis (tert-butoxycarboniPamino 1-pyridin-2-carbonin-6-chloro-1 - (ethoxycarboniPindol • 10 The title compound was prepared in accordance with procedure described in step 1 of Example 366 and step 2 of Example 1 employing 4- [N, Nb.sup.-tert-butoxycarbonyl) amino] -2-chloropyridine (step 1). NMR (CDCl.sub.3) d: 8.38 (1 H, d, J = 5.4 Hz), 7.19 (1 H, d, J = 1.8 Hz), 7.05 (1 H, dd, J = 1.8, 5.4), 1.47 (18 H, s) 15 Step 2. 3 -Amno-2-r4-fN, N-bis (tert-butoxycarboniPamino-1-pyridin-2-carbonin-6-chloro-1 - (ethoxycarboniPindol) The title compound was prepared according to the procedure described in step 1 of Example 366 and step 2 of Example 1 employing 4- [N, Nb 's (tert-butoxycarbonyl) amino] -2-chloropyridine (step 1). NMR (CDCl 3) d: 8.59 (1 H, d, J = 5.3 Hz), 8.24 (1 H, d, j = 1.6 Hz), 7.88 (1 H, d, J = 2.1 Hz), 7.52 (1 H, d, J = 8.4 Hz), 7.27-7.23 (1 H, m), 7.20 (1 H, dd, J = 2.0, 5.2 Hz), 5.97 (2 H, sa), 3.82 (2 H, q, J = 7.1 Hz), 1.49 (18 H, s), 0.95 (3 H, t , J = 7.1 Hz).

Step 3. 2-f4-ÍN, NBs (tert-butoxycarboniPaminolpyridin-2-carbonyl-1-6-chloro-1-ethoxycarbonyl-3- (propionylamino) indole The title compound was prepared from according to the procedure described in step 1 of Example 2 (Procedure A) employing 3-Amino-2- [N, Nbys (tert-butoxycarbonyl) amino] pyridine-2-carbonyl] -6-chloro-1 - (ethoxycarbonyl) indole (step 2) and propionyl chloride H-NMR (CDCU) d: 9.52 (1 H, sa), 8.61 (1 H, d, J = 5.1 Hz), 8.21 (1 H, d, J = 1.8 Hz), 8.05 (1 H, d, J = 8 J Hz), 7.95 (1 H, d, J = 2.1 Hz), 7.28-7.23 (2 H, m), 3.93 (2 H, q, J = 7.1), 2.51 (2 H, q, J = 7.4 Hz), 1.50 (18 H, s), 1.26 (3 H, t, J = 7.4 Hz), 1.02 (3 H, t, J = 7.1).

Step 4. 2-f4- (t-ButoxycarboniPaminopyridin-2-carbonyl-6-chloro-3- (propionylamino) indole To a solution of 2- [4- [N, N-bis (tert- butoxycarbonyl) amino] -2-pyridine-2-carbonyl] -6-chloro-1-ethoxycarbonyl-3- (propionlamino) ethylene (step 3, 240 mg, 0.391 mmol) in Ethanol (10 ml) was added a solution of potassium carbonate (260 mg, 3.91 mmol) in water (5 ml) at room temperature.After stirring for 8 h the mixture was concentrated.The residue was diluted with ethyl acetate (100 ml). ml) and washed with (50 ml x 2), dried (NaSO 4). Removal of the solvent gave an oily residue which was purified by flash chromatography eluting with ethyl acetate / hexane (1/3) to give 118 mg (68 mL). %) of the title compound as an oil NMR (CDCl 3) d: 11.97 (1 H, sa), 10.87 (1 H, sa), 8.55 (1 H, d, J = 5.8 Hz), 8.49 (1 H, d, J = 9.1 Hz), 8.08 (1 H, d, J = 2.0), 7.79 (1 H, dd, J = 2.1, 5.8 Hz), 7.36 (1 H, J = 1.3), 7.02 (1 H, dd, J = 1.8, 5.8 Hz), 6J5 (1 H, sa), 2.60 (2 H, q, J = 7.5 Hz ), 1.56 (9 H, s), 1.36 (3 H, t, J = 7.5 Hz).

Step 5. 2- (4-Aminopyridine-2-carbon-P-6-chloro-3- (propionylamino) indole 2- [4- (tert-butoxycarbonyl) aminopyridine-2-carbon) hydrochloride l] -6-chloro-3- • 10 (propionylamino) indole (step 4, 118 mg, 0.266 mmol) was treated with trifluoroacetic acid (4 ml) at room temperature for 1 h. The mixture was concentrated and azeotropically evaporated with toluene giving an oily residue The residue was basified with saturated sodium bicarbonate in water (30 ml) and extracted with dichloromethane (30 ml x 3) The organic phase was dried (K2CO3) and concentrated to give the free base of the title compound. The free base was dissolved in 10% HCI-MeOH (4 ml) and then evaporated. He • residue obtained was crystallized from ethanol-diethyl ether to give the title compound, mp: 199-204 ° C (decomposition) NMR (DMSO-d6) d: 12.03 (1 H, sa), 10.41 (1 H, sa), 8.17 (1 H, d, J = 7.3 Hz), 7.93 (1 H, d, J = 8.9 Hz), 7.48 (1 H, d, j = 1.6 Hz), 7.18 (1 H, dd, J = 1.6, 8J Hz), 7.12 (1 H, d, J = 1.8 Hz), 6.88 (1 H, dd, J = 7.4, 2.0 Hz ), 2.18 (1 H, q, J = 7.4 Hz), 0.82 (3 H, t, J = 7.4 Hz). A signal due to NH2 was not observed.

• Step 1. 3-Aceto-imethyl-2- (bromoacetyl) furan 5 It was dissolved in acetic acid (30 ml) 3-acetoxymethyl-2-acetylfuran (1.7 g, 9.3 mmol), prepared according to the procedure described in Acta. Chemica. Scandinavia, 1990, 44, 916). To the solution was added pyridinium tribromide (3.3 g, 10.2 mmol) and the resulting mixture was stirred at room temperature for 3 h. The mixture was cooled to 0 ° C and added drop a drop sodium bicarbonate saturated in water until the solution was basic. The mixture was extracted with ethyl acetate (100 ml). The organic extract was washed with brine (100 ml), dried (MgSO) and concentrated to give 2.3 g (95%) of the title compound. NMR (CDCl 3) d: 7.54 (1 H, d, J = 1.6 Hz), 6.65 (1 H, d, J = 1.6 Hz), 5.38 (2 H, s), 4.37 (2 H, s), 2.09 (3 H, s). 15 Step 2. 3-Amino-6-chloro-1-ethocycarbonyl-2- (3-hydroxyethyl-2-furoiPindol To a suspension of sodium hydride (60% w / w dispersion in mineral oil, 390 mg, 8.8 mmol) in DMF (20 ml) was added a solution of 4-Chloro-2- (ethoxycarbonyllamino) benzonitrile (step 1, 2 g, 8.8 mmol) in DMF (5 ml) at 0 ° C. After stirring for 1 h at 0 ° C, 3-acetoxymethyl-2- (bromoacetyl) furan (step 1, 2, 3 g, 8.8 mmol) was added and the resulting mixture was stirred at room temperature for a further 6 h. The mixture was poured into water (100 ml) and extracted with ethyl acetate (300 ml). The organic extract was washed with saturated sodium bicarbonate in water (100 ml), brine (100 ml) and then dried (MgSO) and concentrated. The residue was diluted with a mixture of ethanol (20 ml) and water (10 ml) and then potassium carbonate (approximately 2 g) was added. After stirring for 6 h the mixture was poured into saturated aqueous ammonium chloride (100 ml) and the mixture was extracted with ethyl acetate (300 ml). The organic extract was washed with brine (100 ml), dried (MgSO) and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate / hexane (2/1) to give 505 mg (16%) of the title compound as yellow solids. Dough; M + = 362.

Step 3. 3-Acetylamino-6-chloro-1-ethoxycarbonyl-2- (3-acetoxymethyl-2-furoiPindol To a solution of 3-amino-6-chloro-1-ethoxycarbonyl] -2- (3-Hydroxymethyl-2-furoyl) indole (step 2, 330 mg, 0.91 mmol) in diethylmethane (10 ml) was added pyridine (2 ml) and acetic anhydride (0.19 ml, 2.0 mmol) at room temperature. for 5 h the mixture was poured into Aqueous 2N HCl (30 ml) and extracted with ethyl acetate (100 ml). The organic phase was washed with water (50 ml), saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml) and then dried (MgSO 4) and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate / hexane (1/1) to provide 382 mg (94%) of the title compound as a yellow solid NMR (CDCl 3) d: 10.2 (1 H, s), 8.11 (1 H, d, J = 1.1 Hz), 7.48 (1 H, d, J = 4.8 Hz), 7.05-7.33 (2 H, m), 6.70 (1 H, d, J = 4.8 Hz), 5.41 ( 2 H, s), • 4.25 (2 H, q, J = 7.0 Hz), 2.36 (6 h, s), 1.33 (3 H, t, J = 7. 0 Hz).

Step 4. 3 Acetalamino-6-chloro-2- (3-hydroxymethyl-2-furo-P indole) To a solution of 3-acetylamino-6-chloro-1-ethoxycarbonyl-2- (3-acetoxymethyl-2) -furoyl) indole (step 3, 180 mg, 0.4 mmol) in a mixture of ethanol (10 ml) and water (5 ml) was added 2N aqueous sodium hydroxide (2 ml) • 10 room temperature. After stirring for 1.5 h the mixture was poured into 2N aqueous ammonium chloride (50 ml) and extracted with ethyl acetate (100 ml). The organic phase was washed with brine (50 ml), dried (MgSO 4) and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate / hexane (1/1) and the product was recrystallized from Acetone / hexane gave 98 mg (73%) of the title compound as a yellow crystalline solid. p.f .: 196-198 ° C NMR (CDCl 3) d: 10.6 (1 H, s a), 9.52 (1 • H, sa), 8.33 (1 H, d, J = 9.2 Hz), 7.66 (1 H, sa), 7.30 (1 H, sa), 7.01 (1 H, d, J = 9.2 Hz), 6.66 ( 1 H, sa), 4.81 (2 H, s), 2.32 (3 H, s). The signal due to OH H was not observed.

EXAMPLE 373 6-Chloro-2- (4-hydroxymethyl-2-furoiP-3- (isovalerylamino) indole Step 1. 4-acetoxymethyl-2-bromoacetylPfuran The title compound was prepared according to the procedure described in step 1 of example 372 using 4-acetoxymethyl-2-acetylfuran (prepared according to the procedure described in Acta. Chemica, Scandinavia, 1990, 44, 916). NMR (CDCl 3) d: 7.67 (1 H, s) 7.34 (1 H, s), 5.00 (2 H, s), 4.29 • 10 (2 H, s), 2.09 (3 H, s).

Step 2.2-Í4-acetoxymethyl-2-furoyl) -3-amino-6-chloro-1- (non-toxic rboniPindol The title compound was prepared according to the procedure described in step 2 of Example 1 using 4- chloro-2- (ethoxycarbonylamino) benzonitrile (Example 1, pasol) and 4-acetoxymethyl-2- (bromoacetyl) furan (step 1) 1 H-NMR (CDCl 3) d: 8.26 (1 H, d, J = 1.8 Hz) , 7.55 (1 H, s), 750 (1 H, d, J = 8.4 Hz), 7.27 (1 H, dd, J = 1.8, 8.4 Hz), 7.20 (1 H, s), 5.84 (2 H, sa), 20 4.99 (2 H, s), 4.08 (2 H, q, J = 7.1 Hz), 2.07 (3 H, s), 1.03 (3 H, t, J = 7.1 Hz). procedure described in step 1 of Example 2 (Method A) employing 2- (4-acetoxymethyl-2-furoyl) -3-amino-6-chloro-1 - (ethoxycarbonyl) dol (step 2) and isovaleryl chloride. 1 H NMR (CDCl 3) d: 9.24 (1 H, sa), 8.25 (1 H, d, J = 1.8 Hz), 8.00 (1 H, d, J = 8 J Hz), 7.61 (1 H, s), 7.29 (1 H, dd, J = 1.8, 8.7 Hz), 7.26 (1 H, s), 4.99 (2 H, s), 4.15 (2 H, q, J = 7.1, Hz), 2.34 (2 H, d) , J = 6.6 Hz), 2.17-2.27 (1 H, • 10 m), 2.08 (3 H, s), 1.09 (3 H, t, J = 7.1 Hz), 1.05 (6 H, d, J = 6.4 Hz).

Step 4. 6-chloro-2- (4-acetoxymethyl-2-furoiP-3- (isovalerylamino) indole To a solution of 2- (4-acetoxymethyl-2-furoyl) -6-chloro-1- ethoxycarbonyl-3- (isovalerylamino) indole (step 3, 213.5 mg, 0.437 mmol) in ethanol (1.5 ml) was added 2N aqueous sodium hydroxide (1.5 ml). After stirring for 5.5 h the mixture was poured into saturated ammonium chloride in water • 2N (20 ml) and extracted with ethyl acetate (80 ml). The organic phase was washed with brine (20 ml), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate.

Ethyl / hexane (1/3) and recrystallization from 2-propanol / isopropyl ether gave 119 mg (88%) of the title compound as yellow solids, e.g. f .: 200-201 ° C. NMR (CDCl 3) d: 10.7 (1 H, sa), 9.37 (1 H, sa), 8.47 (1 H, d, J = 8.74 Hz), 7.74 (1 H, s), 7.45 (1 H, s) , 7.38 (1 H, d, J = 1.81 Hz), 7.08 (1 H, dd, J = 1.81 Hz, 8.74 Hz), 4.70 (2 H, d, J = 4.78 Hz), 2.41 (2 H, d, J = 6.38 Hz), 2.35-2.27 (1 H, m), 1.08 (3 H, s), 1.06 (3 H, s). The signal due to OH H was not observed.

EXAMPLE 374 6-Chloro-2- (4-hydroxymethyl-2-furoyl) -3- (propionylamino) indole Step 1. 2- (4-Acetoxymethyl-2-furo-P-6-chloro-1-ethoxycarbonyl-3- (propionylamino) nol) The title compound was prepared according to the procedure described in step 1 of Example 2 (Method A) employing 2- (4-acetoxymethyl-2-furoyl) -3-amino-6-chloro-1 - (ethoxycarbonyl) indole (Example 373, step 2) and propionyl chloride, NMR (CDCl 3) d : 9.29 (1 H, sa), 8.23 (1 H, d, J = 1.65 Hz), 8.00 (1 H, d, J = 8.73 Hz), 7.61 (1 H, s), 7.29-7.28 (2 H, m), 4.99 (2 H, s), 4.15 (2 H, q, J = 7.08 Hz) , 2.51 (2 H, q, J = 7.58 Hz), 2.08 (3 H, s), 1.27 (3 H, t, J = 7.58 Hz), 1.09 (3 H, t, J = 7.08 Hz).

Step 2. 6-Chloro-2- (4-hydroxyethyl-2-furo-P-3- (propionyl) indole To a solution of 2- (4-Acetoxymethyl-2-furoyl) -6-chloro-1-ethoxycarbonyl-3- (propionyl) indole (step 1, 114 mg, 0.313 mmol) in ethanol (2 ml) was added 2N aqueous sodium hydroxide (2 ml). After stirring for 3 h the mixture was poured into 2N aqueous saturated ammonium chloride (20 ml) and extracted with ethyl acetate (80 ml). The organic phase was washed with brine (20 ml), dried (MgSO4) and concentrated. The residue was purified by flash chromatography eluting with ethyl acetate / hexane (1/1) and recrystallization from • 2-Propanol / isopropyl ether gave 46 mg (40%) of the title compound as yellow solids, e.g. f .: 171-172 ° C. NMR (CDCl 3) d: 10.74 (1 H, sa), 9.37 (1 H, sa), 8.45 (1 H, d, J = 9.06 Hz), 7.08 (1 H, s), 7.42 (1 H, s) 7.36 (1 H, d, J = 1.81 Hz), 7.06 (1 H, dd, J = 9.06, 1.81 Hz), 4.67 (2 H, s), 2.58 (2 H, q, J = 7.58, Hz), 1.33 (3 H, t, J = 7.58 Hz) ,. 10 The signal due to H of OH was not observed.

EXAMPLE 375 6-Chloro-2- (4-hydroxymethyl-2-furoyl) -3-rr (s) -2-hydroxypropionyl-amino-1-indole Step 1. 2- (4-acetoxymethyl-2-furoiP-6-chloro-1-ethoxycarbonyl-3-yl (S) -2-acehoxypropionyl aminol indole The title compound was prepared according to the procedure described in step 1 of Example 2 (Method A) employing 2- (4-acetoxymethyl-2-furoyl) -3-amino-6-chloro-1 - (ethoxycarbonyl) indole (Example 373, step 2) and (S) -chloride (-) - 2-acetoxypropionyl, 1 H NMR (CDCl 3) d: 10.03 (1 H, sa), 8.26 (1 H, d, J = 1.81 Hz), 8.21 (1 H, d, J = 8.74 Hz), 7.62 (1 H, s), 7.30 (1 H, dd, J = 8.74 Hz, 1.81 Hz), 7.28 (1 H, s), 5.38 (1 H, q, J = 6.92 Hz), 4.99 (2 H, s ), 4.12 (2 H, q, J = 7.09 Hz), 2.08 (3 H, s), 2.04 (3 H, s), 1.59 (3 H, d, J = 6.92 Hz), 1.26 (2 H, t, J = 7.09 Hz).

Step 2. 6-Chloro-2- (4-hydroxymethyl-2-furo-D-3-rr (s) -2-hydroxypropionylaminolol dol To a solution of 2- (4-Acetoxymethyl-2-furoyl) -6- Chloro-1-ethoxycarbonyl-3 - [(S) -2-acetoxypropionylamino] indole (step 1, 267 mg, 0.494 mmol) in ethanol (2 ml) was added 2N aqueous sodium hydroxide (2 ml). The mixture was poured into 2N aqueous saturated ammonium chloride (20 ml) and extracted with ethyl acetate (80 ml) The organic phase was washed with brine (20 ml), dried (MgSO) and concentrated. purified by flash column chromatography eluting with dichloromethane / methanol (50/1) and recrystallized from 2-propanol / isopropyl ether to give 43 mg (24%) of the title compound as yellow solids, mp: 213-214 ° C NMR (CDCl 3) d: 11.4 (1 H, sa), 10.8 (1 H, sa) 8.35 (1 H, d, J = 8.90 Hz), 7J6 (1 H, s), 7.53 (1 H, d, J = 1.81 Hz), 7.45 (1 H, s) 7.01 (1 H, dd, j = 8.90 Hz, 1.81 Hz), 4.58 (2 H, d, J = 5.11 Hz), 4.36 (1 H, q, J = 6.92, Hz), 1.52 (3 H, d, J = 6.92 Hz).

Step 1. 2-brom? Qcetyl-5-methylthiazole ^ aF The title compound was prepared according to the procedure described in step 4 to Example 370 using 2-acetyl-5-methylthiazole (Bull. Soc. Chim. Fr. , 1953, 702). NMR (CDCl 3) d: 7.70 (1 H, s), 4.65 (2 H, s), 2.59 (3 H, s) Step 2. 3-amino-6-chloro-1-ethoxycarbonyl-2-r2- (5-methylthiazoyl) 1-ddol The title compound was prepared according to the procedure described in step 2 of Example 1 using 4-chloro-2- (ethoxycarbonylamino) benzonitrile (Example 1, step 1) and 2-bromoacetyl-5-methylthiazole (step 1). NMR (CDCl 3) d: 8.23 (1 H, d, J = 1.81 Hz), 7.64 (1 H, d, J = 0.82.

Hz), 7.50 (1 H, d, J = 8.4 Hz), 7.25 (1 H, dd, J = 1.8, 8.4 Hz), 6.02 (2 H, sa) 4.07 (2 H, q, J = 7.08 Hz) , 2.57 (3 H, d, J = 0.82 Hz), 1.00 (3 H, d, J = 0.82 Hz).

Step 3. 3- amino-6-chloro-2- [2- (5-methylalzoyl) 1 indole The title compound was prepared according to the procedure described in step 3 of Example 1 using 3-amino 6-chloro-1-ethoxycarbonyl-2- [2- (5-methylazoyl)] indole. NMR? (CDCl 3) d: 10.4 (1 H, sa), 7.71 (1 H, d, J = 0.82 Hz), 7.51 (1 H, d, J = 8.74 Hz), 7.31 (1 H, d, J = 1.81 Hz ), 6.97 (1 H, dd, J = 1.81, 8.74 Hz), 5.95 (2 H, sa) 2.60 (3 H, d, J = 0.82 Hz).

EXAMPLE 377 • 6-Chloro-3-isovalerylamino-2-r2- (5-methylthiazoyl) 1 indole The title compound was prepared according to the procedure described in Example 19 from 3-amino-6-chloro-2- [2- (5-methylthiazoyl)] dol (Example 376) and isovaleryl chloride. f 10 NMR? (CDCl 3) d: 11.14 (1 H, s a), 10.6 (1 H, s a), 8.52 (1 H, d, J = 8.9 Hz), 7.78 (1 H, d, J = 1.2 Hz), 7.37 (1 H, d, J = 1.8 Hz), 7.05 (1 H, dd, j = 1.8, 8.9 Hz), 2.63 (3 H , d, J = 1.2 Hz), 2.43 (2 H, m) 2.35-2.24 8 (1 H, m), 1.07 (6 H, d, J = 6.4 Hz).

EXAMPLE 378 3-Acetylamino-6-chloro-2-r2- (5-methylthiazoyl) 1 indole To a suspension of sodium hydride (dispersion in mineral oil, 60% w / w, 900 mg, 22.5 mmol) in DMF (30 ml) was added a solution of 4-chloro-2- (ethoxycarbonylamino) benzonitrile (5 g, 22.5 mmol) in DMF (10 ml) at 0 ° C. After stirring for 1 h at 0 ° C, 2-bromoacetyl-5-methylthiazole was added and the resulting mixture was stirred at room temperature for 18 h and then quenched with ethyl acetate (1 ml). The mixture was poured into water (50 ml) and extracted with ethyl acetate (100 ml). The organic phase was washed with saturated aqueous sodium bicarbonate (50 ml) and brine (50 ml). The organic phase was dried (MgSO4) and the solvent was removed. The residue was diluted with 810 ml ethanol) and water (5 ml) and then potassium carbonate (approximately 1 g) was added. The mixture was stirred at room temperature for 4 h and then poured into saturated ammonium chloride in water and extracted with ethyl acetate (100 ml). The phase was washed with brine (50 ml), dried (MgSO) and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate. • ethyl / hexane (1/5) and recrystallization from methanol / dichloromethane / hexane to give 100 mg (4%) of the title compound as yellow solids, e.g. f .: 215-217 ° C. NMR (CDCl 3) d: 11.07 (1 H, sa), 10.5 (1 H, sa), 8.44 (1 H, d, J = 9.2 Hz), 7J5 (1 H, d, j = 1.1 Hz), 7.34 ( 1 H, d, J = 1.8 Hz), 7.03 (1 H, ddJ = 1.8, 9.2 Hz) 2.62 (3 H, s), 2.32 (3 h, s).

EXAMPLE 379 3-Acetylamino-6-chloro-2-f3- (1-methylpyrrolyl) carbonill indole Step 1. 3-Bromoacetyl-1-methylpyrrole The title compound was prepared according to the procedure described in step 4 of Example 370 using 3-acetyl-1-methylpyrrole (Synthesis, 1990, 212).

NMR (CDCl 3) d: 7.34 (1 H, s), 6.61 (2 H, s a), 4.19 (2 H, d, J = 0.66 Hz), 3.71 (3 H, s).

Step 2. 3-Amino-6-chloro-1-ethoxycarbonyl-2- [3- (1-methylpyrrolyl) carbonyl indole The title compound was prepared according to the procedure described in step 2 of Example 1 using 4 -chloro-2 (ethoxycarbonylamino) benzonitrile and 3-bromoacetyl-1-methy1pyrrole (step 1). NMR? (CDCI3) d: 8.22 (1 H, d, J = 1.3 Hz) 7.47 (1 H, d, J = 8.4 Hz), 7.27 (1 H, dd, J = 1.8, 8.4 Hz), 7.18 (1 H, d, J = 1.8 Hz), 6.57-6.55 (2 H, m), 5.38 (2 H, sa), 4.02 (2 H, q, J = 7.1 Hz), 3.67 (3 H, s), 0.98 (3 H, t, J = 7.1 Hz).

Step 3. 6-Chloro-3-diacetylamino-1-ethoxycarbonyl-2- [3- (1-methylpyrrolyl) carbonyl indole To a mixture of 3-amino-6-chloro-1-ethoxycarbonyl-2- [3- (1 -methylpyrrolyl) carbonyl] indole (step 2. 337 mg, 0.95 mmol) and pyridine (89 mL, 1.1 mmol) in dichloromethane (5 mL) was added acetyl chloride (75 mL, 1.05 mmol) at room temperature. After stirring for 1 h, the mixture was poured into 2N aqueous HCl (20 ml) and extracted with ethyl acetate (80 ml). The organic phase was washed with water (20 ml) saturated sodium bicarbonate in water (20 ml) and brine (20 ml), and then dried (MgSO4). Removal of the solvent gave 208 mg (93%) of the title compound as a yellow oil. NMR (CDCl 3) d: 8.30 (1 H, d, J = 1.65 Hz), 7.34 (1 H, dd, a) 4.30 Step 4. 3-Acetylamino-6-chloro-ethoxy-2-benzyl-2-y3- (1-methylpyrrolyl) 5-carbonyl indole 6-Chloro-3-diacetylamino-1-ethoxycarbonyl-2- [3- (1-methylpyrrolyl) carbonyl ] indole (step 3, 200 mg) was diluted with a mixture of ethanol (20 ml) and water (10 ml) and then potassium hydroxide (ca.1 g) was added. After stirring for 4 h at room temperature, the mixture was poured into chloride • 10 saturated aqueous ammonia (20 ml) and extracted with ethyl acetate (80 ml). The organic phase was washed with brine (29 ml), dried (MgSO) and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate / hexane (1/2) to give 45 mg (27%) of the title compound as yellow solids, e.g. f .: 205-206 ° C 15 NMR (CDCl 3) d: 10.7 (1 H, s a), 10.2 (1 H, s a), 8.07 (1 H, d, J = 8.7 Hz), 7.49-7.46 (2H, m), 7.01 (1 H, d, J = 8.7 Hz), 6.73 (2H, m), 3.77 (3H, • s), 2.23 (3H, s).

EXAMPLE 380 20 3- (2-Acetoxyisobutyrylamino) -6-chloro-2- (4-methylpyridine-2-carbonyl) indole The title compound was prepared according to the procedure described in Example 19 using 3-amino-6-chloro-2- (4-methylpyridine-2-carbonyl) indole (Example 70) and 2-acetoxybutyryl chloride. p. f .: 222-223 ° C. 1 H NMR (CDCl 3) d: 12.03 (1 H, s a), 11.45 (1 H, s a), 8.63 (1 H, • d, J = 4.6 Hz), 8.56 (1 H, d, J = 9.2 Hz), 8.17 (1 H, t, J = 0.8 Hz), 7.40 (1 H, d, J = 1.5 Hz), 7.37 ( 1 H, dt, J = 4.9, 0.8 Hz), 7.04 (1 H, dd, J = 8.9, 1.9 Hz), 2.51 (3 H, s), 2.29 (3 H, s), 1.81 (6 H, s ).

EXAMPLE 381 6-Chloro-3- (2-hydroxyisobutyrylamino) -2- (4-methylpyridin-2-carbonyl) indole • The title compound was prepared according to the procedure described in Example 361 using 3- (2-acetoxyisobutylamino) -6-chloro-2- (4-methylpyridine-2-carbonyl) dol (Example 380) .pf: 217-219 ° C. 15 NMR? (CDCl 3) d: 12.07 (1 H, sa), 11.70 (1 H, sa), 8.62 (1 H, dd, J = 4.9, 0.5 Hz), 8.55 (1 H, d, J = 9.1 Hz), 8.21 (1 H, dd, J = 1.0, 0.7 Hz), 7.40 (1 H, dd, J = 2.0, 0.5 Hz), 7.36 (1 H, ddd, J = 5.1, 1.8, 0.7 Hz), 7.05 (1 H , dd, J = 9.1, 1.8 Hz), 2.86 (1 H, sa), 2.48 (3 H, s), 1.67 (6 H, s).

EXAMPLE 382 3-rr (S) -2-Acehoxypropionyl-amino-1-6-chloro-2- (4-methylpyridine-2-carbonyl) indole • The title compound was prepared according to the procedure described in Example 19 using 3-amino -6-chloro-2- (4-methylpyridine-2-carbonyl) indole (example 70) and (S) - (-) -2- acetoxypropionyl chloride. p.f .: 213-214 ° C. NMR? (CDCl 3) d: 12.06 (1 H, s a), 11.53 (1 H, s a), 8.61 (1 H, d, • 10 J = 4.9 Hz), 8.57 (1 H, d, J = 9.1 Hz), 8.16 (1 H, t, J = 0.9 Hz), 7.40 (1 H, dd, J = 1.8, 0.9 Hz), 7.36 (1 H, ddd, J = 4.9, 1.8, 0.8 Hz), 7.05 (1 H, dd, J = 8.9, 1.8 Hz), 5.49 (1 H, q, J = 6.9 Hz), 2.51 (3 H, s ), 2.42 (3 H, s), 1.67 (3 H, d, J = 6.9 Hz).

EXAMPLE 383 15 6-Chloro-3-rr (s) -2-hydroxypropionamino1-2- (4-methylpridin-2-carbonyl) indole The title compound was prepared according to the procedure described in Example 361 using 3 - [[(S) -2- acetoxypropionl] amino] -6-chloro-2- (4-methylpyridin) -2-carbonyl) indole (example 20 382). p.f .: 206-207 ° C. NMR (CDCl 3) d: 12.07 (1 H, sa), 11.52 (1 H, sa), 8.64 (1 H, d, J = 5.1 Hz), 8.54 (1 H, d, J = 9.2 Hz), 8.21 ( 1 H, s), 7.42 (1 H, d, J = 1.8 Hz), 7.38 (1 H, ddd, J = 4.9, 1.7, 0.9 Hz), 7.07 (1 H, dd, J = 9.0, 1.9 Hz) , 4.55 (1 H, sa), 2.89 (1 H, d, J = 4.3 Hz), 2.50 (3 H, s), 1.66 (3 H, d, J = 6.8 Hz). • 6-Chloro-3- (2-chloroacetylamino) -2- (4-methylpyridine-2-carbonyl) indole The title compound was prepared according to the procedure described in Example 19 using 3-amino-6-chloro-2- (4-methylpyridin-2-carbonyl) indole (example 70) and chloroacetyl chloride. p.f .: 224-225 ° C. ^ 10 NMR (CDCl 3) d: 12.12 (1 H, sa), 11.65 (1 H, sa), 8.64 (1 H, d, J = 5.1 Hz), 8.43 (1 H, d, J = 8.7 Hz), 8.23 (1 H, s), 7.43 (1 H, d, J = 1.8 Hz), 7.39 (1 H, ddd, J = 4.4, 1.0, 0.6 Hz), 7.07 (1 H, dd, J = 9.2, 2.0 Hz), 4.32 (2 H, s), 2.50 (3 H, s).

EXAMPLE 385 6-Chloro-3-F2- (N, N-dimethylamino) acetylamino1-2- (4-methylpyridin-2 -carbonyl) indole The title compound was prepared according to the procedure described in step 2 of example 122 using 6-chloro-3- (2-chloroacetylamino) -2- (4-methylpyridine-2-carbon) Idol (example 384). p.f .: 193-194 ° C. NMR (CDCl 3) d: 12.08 (1 H, sa), 11.67 (1 H, sa), 8.62 (1 H, d, J = 4.9 Hz), 8.48 H, dd, J = 2.0, 0.5 Hz), 7.36 ( 1 2.0 Hz), 3.24 (2 H, s), 2.51 (6 H, s), 2.50 (3 H, s).

EXAMPLE 386 6-Chloro-3- (3-chloropropionylamino) -2- (4-methylpyridin-2-carbonyl) nol The title compound was prepared according to the procedure described in Example 19 using 3-amino-6-chloro-2- (4-methylpyridine-2-carbonyl) indole (example 70) and 3-chloropropionyl chloride. NMR (CDCl 3) d: 11.96 (1 H, sa), 10.97 (1 H, sa), 8.60 (1 H, d, J = 4.9 Hz), 8.44 (1 H, d, J = 8.9 Hz), 8.14 ( 1 H, s), 7.35-7.39 (2 H, m), 7.04 (1 H, dd, J = 9.1, 1.5 Hz), 3.96 (2 H, t, J = 6.7 Hz), 3.03 (2 H, t , J = 6.7 Hz), 2.50 (3 H, s).

EXAMPLE 387 6-Chloro-3-r3-n, n-dimethylamino) propionyl-aminol-2- (4-methylpyridin-2-carbonyl) indole The title compound was prepared according to the procedure described in step 2 of example 122 using 6-chloro-3- (3-chloropropionyl amine) -2- (4-methylpyridin-2-carbonyl) ) indole (example 386). p.f .: 170-171 ° C.

NMR? (CDCl 3) d 12.04 (1 H, s a), 11.37 (1 H, s a), 8.62 (1 H, d, J = 5.1 Hz), 8.33 (1H, d, J = 9.1 H% 8.17 (1 H, t, J = 0.8 Hz), 7.40 (2 H, dd, J = 1.9, "" '- 0.6 Hz), 7.36 (1 H, ddd, J = 4.9, 1.8, OS Hz), 7.32 (1 H, dd, J = 9.0, 1.9 Hz), 2J8- 2.84 (2 H, m), 2.68-2J4 (2H, m), 2.51 (3 H, s), 2.39 (6 H, s).

EXAMPLE 388 6-Chloro-2- (3-hydroxymethyl-2-furoyl) -3- (2-isobutyrylamino) indole Step 1. 2- (3-acetoxymethyl-2-furoyl) -3-amino-6-chloro-1- • 10 (ethoxycarbonyl) indole The title compound was prepared according to the procedure described in step 2 of example 1 from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 3-acetoxymethyl-2- (bromoacetyl) furan (example 372, step 1). 15 NMR (CDCl 3) d: 8.27 (1 H, d, J = 1.3 Hz), 7.51 (1 H, d, J = 8.2 Hz), 7.43 (1 H, d, J = 1.6 Hz), 7.27 (1 H, dd, J = 2.0, 8.4 Hz), 6.60 (1 H, d, J = 1.6 • Hz), 5.50 (2 H, s), 4.03 (2 H, q, J = 7.1 Hz), 2.14 (3 H, s), 1.03 (3 H, t, J = 7.1 Hz).

Step 2. 2- (3-Acetoxymethyl-2-furoiP-6-chloro-1-ethoxycarbonyl-3- (isobutyrylamino) ndol The title compound was prepared according to the procedure described in step 1 of the example 2 using 2- (3-acetoxymethyl-2-furoyl) -3-amino-6-chloro-1 - (ethoxycarbonyl) ddol (step 1) and isobutyryl chloride.

Step 3. 6-Chloro-2- (3-hydroxymethyl-2-furo-P-3-p-butyrylamino) ndol The title compound was prepared according to the procedure described in step 4 of example 373 using 2 - (3-acetoxymethyl-2-furoyl) -6-chloro-1-ethoxycarbonyl-3- (isobutyrylamino) indole (step 2). p.f .: 170-171 ° C. NMR (CDCl 3) d: 10.87 (1 H, sa), 9.47 (1 H, sa), 8.52 (1 H, d, J = 8.9 Hz), 7.71 (1 H, d, J = 1.6 Hz), 7.37 ( 1 H, d, J = 1.3 Hz), 7.08 (1 H, dd, J = 9.0, 1.8 Hz), 6.68 (1 H, d, J = 1.8 Hz), 4.83 (2 H, d, J = 6.8 Hz), 4.57 (1 H, t, J = 6.9 Hz), 2.71- 2.82 (1 H, m), 1.37 (6 H, d, J = 6.9 Hz).

EXAMPLE 389 2- (2-Amino-5-chlorobenzoiP-6-chloro-3-propionylamino) indole Step 1. 3-amino-6-chloro-2- (5-chloro-2-nitrobenzoyl) -1- • ( ethoxycarbonyl) indole The title compound was prepared according to the procedure described in step 2 of Example 1 from 4-chloro-2- (ethoxycarbonylamino) benzonitrile (example 1, step 1) and 5-chloro-bromide. 2- nitrofenacílo (Schofield, K .; and Simpson, JCE; J. Chem. Soc, 1947, 1170-1174). NMR (CDCl 3) d: 8.12 (1 H, d, J = 1.8 Hz), 7.95 (1 H, d, J = 8.4 ?? »_ - Hz), 7.56-7.48 (3H, m), 7.31 (f, dd, J = 1.6, 8.4 Hz), 6.32 (2 H, sa), 3.99 (2 H, q, J = 7.1 Hz ), 1.09 (3 H, t, J = 7.1 Hz).

Step 2. 3-Amino-6-chloro-2- (5-chloro-2-nitrobenzoiPdol) • The title compound was prepared according to the procedure described in step 3 of Example 1 from 3-amino- 6-chloro-2- (5-chloro-2-nitrobenzoyl) -1- (ethoxycarbonyl) idol (step 1), mp: 233-234 ° C. IR (KBr) v. 3439, 1626, 1512, 1337, 1312, 1267, 1242, 1061, 880 cm "1. • 10 NMR (DMSO-de) d: 10.26 (1 H, sa), 8.25 (1 H, d, J = 8 J Hz), 7.92 (1 H, d, J = 8 J Hz), 7.86 (1 H, dd , J = 2.3, 8.7 Hz), 7.77 (1 H, d, J = 2.3 Hz), 7.15 (1 H, d, J = 1.6 Hz), 6.97 (2 H, sa), 6.95 (1 H, dd, J = 1.6, 8.6 Hz).

Step 3. 6-Chloro-2- (5-chloro-2-n-tetrabenzoyl) -3-propionylamino) ddol The title compound was prepared according to the procedure described in Example 19 from 3 -amino-6-chloro-2- (5-chloro-, 2-nitrobenzoyl) indole (step 2) and propionyl chloride. p.f .: 245-246 ° C. IR (KBr) v: 3078, 1665, 1628, 1580, 1526, 1497, 1340, 1313, 1238, 1022, 843 cm "1. 20 NMR (DMSO-de) d: 12.09 (1 H, sa), 9.26 ( 1 H, sa), 8.29 (1 H, d, J = 8J Hz), 7.87 (1 H, dd, J = 2.3, 8.7 Hz), 7.66 (1 H, d, J = 2.0 Hz), 7.49 (1 H, d, J = 8.6 Hz), 7.46 (1 H, d, J = 2.0 Hz), 7.11 (1 H, dd, J = 1.8, 8J Hz), 1.89 (2 H, q, J = 7.9 Hz) , 0.84 (3 H, t, J = 7.9 Hz).

Step 4. 2- (2-amino-5-chlorobenzoyl) -6-chloro-3- (propionylamino) indole A suspension Se 6-chloro-2- (5-chloro-2-nitrobenzoyl) -3- (propionylamino) ndol (step 3, 450 mg, 1.33 mmol), ammonium chloride (35.6 mg, 0.665 mmol), iron powder (391 mg, 6.65 mmol), ethanol (20 ml) and water (10 ml) was heated to the temperature of reflux for 1 h. After cooling the mixture to room temperature it was filtered through a pad of Celite. The filtrate was concentrated giving a crystalline residue. Purification by flash column chromatography eluting with ethyl acetate / hexane (1: 3) gave 394 mg (79%) of 2- (2-amino-5-chlorobenzoyl) -6-chloro-3- (propionylamino) indole. NMR? (CDCl 3) d: 11.67 (1 H, sa), 9.76 (1 H, sa), 7.58 (1 H, d, J = 8.6 Hz), 7.43 (1 H, d, J = 1.5 Hz), 7.35 (1 H, d, J = 2.5 Hz), 7.26 (1 H, dd, J = 2.5, 8.9 Hz), 7.09 (1 H, dd, J = 1.8, 8.6 Hz), 6.99 (2 H, sa), 6.83 ( 1 H, d, J = 8.9 Hz), 2.12 (2 H, q, J = 7.6 Hz), 0.90 (3 H, t, J = 7.6 Hz).

EXAMPLE 390 2- (2-Amino-5-chlorobenzoyl) -6-chloro-3- (propionylamino) indole hydrochloride It was dissolved in 10% HCl-methanol (10 ml) 2- (2-amino-5-chlorobenzoyl) -6-chloro-3- (propionylamine) indole (example 389, 394 mg) and the solvent was removed. The residue was crystallized from ethyl acetate / ethanol to give 175 mg (41%) of the title compound, mp 184-185 ° C. IR (KBr) v: 3200, 1618, 1541, 1491, 1321, 1232, 1061, 920 cm "1. NMR (DMSO-de) d: 11.70 (1 H, sa), 9J9 (1 H, sa), 7.59 (2 H, da, J = 8.6 Hz), 7.44 (1 H, d, j = 1.6 Hz), 7.36 (1 H, d, J = 2.5 Hz), 7.28 (1 H, dd, j = 2.5, 8J Hz), 7.10 (1 H, dd, J = 1.6, 8.6 Hz), 6.85 (1 H, d, J = 8 J Hz), 2.12 (2 H, q, J = 7.6 Hz), 0.89 (3 H, t, J = 7.6 Hz).

EXAMPLE 391 2- (2-Acetylamino-5-chlorobenzoyl) -6-chloro-3- (propionylamino) indole To a solution of 2- (2-amino-5-chlorobenzoyl) -6-chloro-3- (propionylamino) indole (example 389, 217 mg, 0.576 mmol) and pyridine (0.12 mL, 1.50 mmol) in dichloromethane (10 mL) Acetyl chloride (35 μL, 0.749 mmol) was added at 0 ° C. After stirring at room temperature for 1 h the mixture was concentrated and the residue was diluted with ethyl acetate (100 ml). The solution was washed with 2N aqueous HCl (30 ml x 2), saturated aqueous sodium bicarbonate (30 ml) and dried (MgSO 4). Removal of the solvent gave a crystalline residue. Recrystallization from ethyl acetate gave 163 mg (68%) of the title compound, m.p.:264-266 ° C. IR (KBr) v: 3260, 1676, 1655, 1578, 1547, 1508, 1313, 1234, 1205, 1006, 918, 841 cm "1. NMR (DMSO-de) d: 11.77 (1 H, sa), 10.09 (1 H, sa), 9.39 (1 51 H, sa), 7.77 (1 H, d, J = 8.4 Hz), 7.63 (1 H, d, J = 8 J Hz), 7.60 (1 H, dd, J = 1.5, 8.1 Hz), 7.44 (1 H , s), 7.40 (1 H, d, J = 2.6 Hz), 7.09 (1 H, d, j = 8.7 Hz), 2.02 (2 H, q, j = 7.7 Hz), 1.93 (3 H, s) , 0.84 (3, H, t, J = 7J Hz).

• EXAMPLE 392 6-Chloro-2-r3- (hydroxymethyl) pyridine-2-carbon-p-3- (propionylamino) indole Step 1. 3-tert-butyldimethyl-1-oxoxymethyl-2-chloropyridine To a solution of 2-chloro-3- (hydroxymethyl) pyridine (Read, M. W; yf 10 Ray, P: S :; J. Heterocyclic Chem., 1995, 32, 1595-1597., 2.81 g, 19.1 mmol) and imidazole (3.25 g, 47.7 mmol) in N, N-dimethylformamide (30 mL) was added tert-butyldimethylsilyl chloride (3.74. g, 24.8 mmol) at 0 ° C. The mixture was allowed to warm to room temperature and was stirred for 17 h. The solution was diluted with diethyl ether (200 ml) and the resulting solution was washed with water (100 ml × 3) and dried (MgSO). Removal of the solvent gave an oily residue. Purification by flash chromatography eluting with acetate ff, ethyl / hexane (1: 15) gave 3.61 g (73%) of the title compound. 1 H NMR (CDCl 3) d: 8.28 (1 H, dd, J = 2.0, 4.7 Hz), 7.91 (1 H, dd, J = 2.0, 8.1 Hz), 7.28 (1 H, dd, J = 4.8, 8.1 Hz), 4.75 (2H, s), 0.97 (9H, s), 0.15 20 (6H, s).

Step 2.2-bromoacetyl-3- (tert-butyldimethylsyl) methyl) pyridine The title compound was prepared according to the procedure described in step 1 of example 366 using 3 -tert-butyldimethylsilyloxymethyl-2-chloropyridine (step 1). 1 H NMR (CDCl 3) d: 8.56 (1 H, dd, J = 1.8, 4.6 Hz), 8.27 (1 H, dd, • J = 1.8, 7.9 Hz), 7.54 (1 H, dd, J = 4.7, 7.8 Hz), 5.13 (2H, s), 4.92 (2H, s), 0.97 (9H, s), 0.14 (6H, s ).

Step 3. 3-Amino-2-y3- (tert-Butyldimethyl-methyloxymethyl) -Pyridyl-2-carbonyl-1-6-chloro-1 - (ethoxycarboniPindol) The title compound was prepared according to the procedure described in step 2 of example 1 employing 4-chloro-2- (ethoxycarbonylamino) benzontrotyl (example 1, step 1) and 2-bromoacetyl-3- (tert-butylmethylsilyloxymethyl) pyridine (step 2). CDCI3) d: 8.42 (1 H, da, J = 4.6 Hz), 8.21-8.16 (2H, m), 7.50 (1 H, d, J = 8.4 Hz), 7.38 (1 H, dd, J = 4J, 7.7 Hz), 7.24 (1 H, dd, J = 1.8, 8.4 15 Hz), 5.96 (2H, sa), 5.17 (2H, s), 3.69 (2H, q, j = 7.1 Hz), 0.99 (9H, s), 0.93 (3H, t, J = 7.1 Hz), 0.17 (6H, s).

Step 4. 2- [3- (tert-butyldimethylsilyloxymethylpyridin-2-carbonin-6-chloro-1-ethoxycarbonyl-3- (propionyllamine) ethylene) of the title was prepared according to the procedure described in step 1 of Example 2 employing 3-amino-2- [3- (tert-butylmethylsilyloxy-methy1) pyridin-2-carbonyl] - 6-chloro-1- (ethoxycarbonyl) indole (step 3) and propionyl chloride, 1 H-NMR (CDCl 3) d: 9.48 (1 H, sa), 8.45 (1 H, dd, J = 1.5, 4.5 Hz), 8.25 (1 H, dd, J = 1.5, 8.1 Hz), 8.16 (1 H, d, J = 1.8 Hz), 8.08 (1 H, d, J = 8.9 Hz), 7.44 (1 H, dd, J = 4S , 7.9 Hz), 7.25 (1 H, dd, J = 1.8, 8.8 Hz), 5.20 (2H, s), 3.86 (2H, q, J = 7.1 Hz), 2.50 (2H, q, J = 7.6 Hz) , 1.26 (3H, t, J = 7.6 Hz), 1.00 (9H, s), 1.00 (3H, t, J = 7.0 Hz), 0.18 (6H, s).

Step 5. 2- [3- (tert-Butyldimethylsilyloxymethyl) pyridn-2-carbonyl] -6-chloro-3- (propionyl-amino) indole solution of 2- [3- (tert-butyldimethylsilyloxymethyl) pyridine-2-carbonyl] -6-chloro-1-ethoxycarbonyl-3- (propylamilane) indole (step 4, 890 mg, 1.64 f 10 mmol) in ethanol-THF (2: 1, 30 ml) was added 2N aqueous NaOH (5 ml) at 0 ° C. After stirring for 1.5 h the mixture was neutralized with 2N aqueous HCl (5 ml). The mixture was concentrated and the residue was diluted with ethyl acetate (200 ml). The organic solution was washed with water (50 ml x 2), dried (MgSO 4) and concentrated. The residue was purified by flash column chromatography eluting with ethyl acetate / hexane (1: 15) to provide 663 mg (82%) of the title compound. f NMR (DMSO-de) d: 11.53 (1 H, sa), 10.75 (1 H, sa), 8.67 (1 H, d, J = 3.8 Hz), 8.45 (1 H, d, J = 8.9 Hz) , 8.41 (1 H, d, J = 8.1 Hz), 7.59 (1 H, dd, J = 4.8, 8.2 Hz), 7.37 (1 H, d, J = 2.0 Hz), 7.04 (1 H, dd, J = 1.8, 8.9 Hz), 5.26 (2H, s), 2.63 (2H, q, J = 7J Hz), 1.36 (3H, t, J = 7.7 Hz), 0.99 (9H, s), 0.18 (6H, s). carbonyl] -6-chloro-3- (propionylamino) indole (step 5, 544 mg, 1.15 mmol) and acetic acid (0.20 ml, 3.50 mmol) in THF (30 ml) was added tetra (n-butylammonium) fluoride ( 1 M in THF, 3.5 ml, 3.50 mmol) at 0 ° C. The mixture was stirred for 4.5 h at the same temperature and diluted with diethyl ether (200 ml). This solution was washed with saturated aqueous sodium bicarbonate (50 ml), water (50 ml x 2) and dried (MgSO 4). Removal of the solvent gave a crystalline residue. Recrystallization from ethyl acetate gave 361 mg (88%) of the title compound, mp: 198-199 ° C IR (KBr) v: 3250, 1663, 1624, 1607, 1578, 1541, 1472, 1352, 1211, 1178 , 1153, 1974, 1045, 1013, 833, 808, 716 cm "1. NMR (CDCl 3) d: 11.33 (1 H, sa), 10.74 (1 H, sa), 8J5 (1 H, dd J = 1.6, 4.8 Hz), 8.47 (1 H, d, J = 9.1 Hz), 8.00 (1 H, dd, J = 1.5, 7.7 Hz), 7.57 (1 H, dd, j = 4.8, 7.7 Hz), 7.36 (1 H, d, J = 1.8 Hz), 7.05 (1 H, dd, J = 1.8 and 9.1 Hz), 4.87 (2 H, d, J = 7.3 Hz), 4.00 (1 H, t, J = 7.1 Hz), 2.62 (2H, q, J = 7.6 Hz), 1.36 (3H, t, J = 7.6).

EXAMPLE 393 3-Acetylamino-2-benzoyl-7-chloroindole Step 1. 7-Chloro-3-nitroindole-2-carboxylic acid Seventy percent nitric acid (3.4 ml) was added dropwise to acetic anhydride (35 ml) under stirring at room temperature. Carefully mix 7-8 J4 mmol). After filter cake was washed with • hexane and dried with air. The yield of 7-chloro-3-nitroindol-2-carboxylic acid, yellow solids, was 283 mg (14%). 1H NMR (DMSO-d6) d: 13.66 (1H, sa), 8.04 (1H, dd, J = 1.1, 8.1 Hz), 7.53 (1 H, dd J = 1.1, 7.7 Hz), 7.42 (1 H, dd , J = 7J, 8.1 Hz).

Step 2. 7-Chloro-2 - [(N-methoxy-N-methylamino) carbonyl1-3-nitroindole 10 A solution of 7-chloro-3-n-trodoindole-2-carboxylic acid (step 1, 400 mg, 1.7 mmol) in thionyl chloride (2 ml) was heated at 70 ° C for 3 h, the mixture was cooled and concentrated. The residue was dissolved in dichloromethane (20 ml). To the solution was added N, O-d-methylhydroxylamine hydrochloride (326 mg, 3.4 mmol) and pyridine (0.27 mL, 3.4 mmol). After stirring for 16 h the mixture was poured into water (100 ml) and extracted with ethyl acetate (200 ml). The organic phase was washed with 2N aqueous HCl (100 ml), water (100 ml), saturated aqueous sodium bicarbonate (100 ml), brine (100 ml) and dried (MgSO4). After removing the solvent, the residue was purified by flash column chromatography eluting with ethyl acetate / hexane (1: 10: 1: 1) to give 420 mg (87%) of the title compound, tic: Rf = 0.55 ( 25% ethyl acetate in hexanes) Step 3. 3-amino ^ 7-chloro-2-f (NH-methoxy-N-methylamine) carbonnindol To a solution d® -chloro-2- [(N-methoxy-N-methylamino) carbonyl] -3-nitroindole (step 2, 420 mg, 1.5 mmol) in ethanol-water (2: 1, 30 ml) was added iron powder (168 mg, 3 mg). mmol) and ammonium chloride (160 mg, 3 mmol). The mixture was heated at 50 ° C for 2 h and then cooled to room temperature. After filtering through a celite layer the filtrate was concentrated. The residue was purified by flash chromatography eluting with ethyl acetate / hexane (1: 10 * 1: 1) to give 287 mg (75%) of the title compound. 1 H NMR (CDCl 3) d: 8.56 (1 H, sa), 7.46 (1 H, d, J = 7.9 Hz), 7.28 (1 H, d, J = 7.6 Hz), 6.94 (1 H, t, J = 7.6, 7.9 Hz), 5.27 (1 H, sa), 3.82 (3H, s), 3.6 (3H, s).

Step 3-acetylamino-7-chloro-2-f (N-methoxy-N-methylamino) carbonyl] dol A to a solution of 3-amino-7-chloro-2 - [(N-methoxy-N-methylamino ) carbonyl] indole (step 3, 287 mg, 1, mmol) in dichloromethane (10 ml) were added pyridine (2 ml) and acetic anhydride (0.16 ml, 1.7 mmol) at room temperature. After stirring for 3 h the mixture was poured into water (100 ml) and extracted with ethyl acetate (150 ml). The organic phase was washed with 2N aqueous HCl (100 ml), water (100 ml), saturated aqueous sodium bicarbonate (100 ml), brine (100 ml) and dried (MgSO). After removing the solvent, the residue was purified by flash column chromatography r ~ « EtOAc acetate (? 1.1) yielding 320 mg (98%) of the title compound. NMR (CDCl 3) d: 9.95 Hz), 8.08 • (1H, d, J = 8.4 Hz), 7.31 (1 H, d, J = 7.6 Hz), 3.82 Step 5. 3-acetylamino-2-beiMp-7- ~ chloroindole To a solution of 3-acetylamino-7-chloro-2 - [(N-methoxy-N-methylamino) carbonyldol (step 4, 321 mg, 1.08 mmol ) in diethyl ether- • 10-tetrahydrofuran (1: 1, 10 ml) was added phenyllithium (1 M solution in cyclohexane, 5.4 ml, 5.42 mmol) at -78 ° C. After stirring for 1 h the mixture was allowed to warm to 0 ° C and was stirred for an additional 2 h. The mixture was quenched with saturated aqueous ammonium chloride (20 ml) and extracted with ether (150 ml). The organic phase was washed with water (50 ml) and dried (MgSO). The elimination of The solvent gave an oily residue. Purification by flash column chromatography eluting with ethyl acetate / hexane (1: 3) provided yellow crystals. Recrystallization from ethyl acetate gave 87 mg (26%) of the title compound, mp: 185-188 ° C IR (KBr) v: 3240, 1690, 1628, 1543, 1375, 1315, 1250, 725 cm "1. NMR (CDCl 3) d: 9.77 (1 H, sa), 8.36 (1 H, sa), 8.18 (1 H, d, J = 8.6, Hz), 7.87-7.83 (2H, m), 7.71-7.57 (3H, m), 7.40 (1 H, dd, J = 1.0, 7.6 Hz), 7.10 (1 H, dd, J = 7.6, 8.4 Hz), 2.26 (2H, s). The chemical structures of the compounds prepared in Examples 1 to 393 are summarized in the following tables.

(Ex. # LXY R1 R¿ Q 1 0 6-CI HH phenyl 2 0 6-CI H CH3-C (O) - phen i lo 3 0 6-CI H (CH3) 2C (O) - phenyl 4 0 6 -CI H phenyl-C (O) -phenyl 5 0 6-CI H C2H5-C (O) -phenyl 6 0 6-CI H CH2 = CH-C (O) -phenyl 7 0 6-CI H C3H7-C (O) - phen i lo • 10 8 0 6-CI H cyclohexyl-C (O) - phenyl 9 0 6-CI H (CH3) 3C-C (O) - phenyl 10 0 6-CI H (CH3) 2CH -CH2-C (O) - phenyl 11 0 6-CI H cyclopropyl-C (O) -phenyl 12 0 6-CI H C4H9-C (O) - phen i lo 13 0 6-CI H 2 -thien? LC (O) - phenyl 14 0 6-CI H phenyl- (CH 2) 2-C (O) -phen i lo 0 0 6-CI H F 3 C-C (O) -phenyl 16 0 6-CI H CH 3 -O- CH2-C (O) -phenyl 17 0 6-CI H CH 3 -C (O) -4-methox-phenyl 18 0 6-CI H H 3-methox? Phenyl 19 0 6-CI H CH3-C (O) -3-methoxyphenyl 0 6-CI H CH3-C (O) -2-methylphenyl 21 0 6-CI H H 3-met? Lphenyl 22 0 6-CI H CH3-C (O) - 3-methylphenol 23 0 6-CI H C2H5-C (O) - 3-methylphenol 24 0 6-CI H C3H7-C (O) - 3-methylphenol Ex. # LXY * "R1 R2 Q 25 0 6-CI H C4H9-C (O) -3-methylphenyl 26 0 6-CI H (CH3) 2CH-CH-3-methylphenyl C (O) - 27 0 6- CI H CH3-O-CH2-C (O) -3-methylphenyl 28 0 6-CI H CH3-C (O) -4-methylphenyl • 29 or 6-CI H CH3-C (O) -2-chlorophenyl 30 or 6-CI HH 3-chlorophenyl 31 0 6-CI H CH3-C (O) -3-chlorophenyl 32 or 6-CI H C2H5- C (O) -3-chlorophenyl 33 0 6-CI H C3H7-C (O) -3-chlorophenyl 34 0 6-CI H C4H9-C (O) -3-chlorophenyl 35 0 6-CI H (CH3) 2CH -CH2- 3-chlorophenyl C (O) - 36 0 6-CI H CH3-O-CH2-C (O) -3-chlorophenyl 37 0 6-CI H CH3-C (O) -4-chlorophenol 38 0 6-CI H CH 3 -C (O) -3-fluorophenyl 39 0 6-CI H CH 3 -C (O) -4-fluorophenyl 10 40 0 6-CI HH 4-CH 3 S-phenyl 41 0 6-CI H CH 3 -C (O) -4-CH3S-phenyl 42 0 6-CI HH 3-bromophenyl 43 or 6-CI H CH 3 -C (O) -3-bromophenyl 44 0 6-CI H CH 3 -C (O) -3 -benzyloxyphenyl 45 0 6-CI H CH3-C (O) -3-hydroxyphenyl 46 0 6-CI H CH3-C (O) - 3,4-dichlorophenyl 47 0 6-CI H H 3,5-difluorophenyl 48 0 6-CI H CH3-C (O) - 3,5-difluorophenyl 49 0 6-CI HH 3-F3C-phenyl 50 0 6-CI H (CH3) 2CH-CH-3-F3C-phenyl 15 C (O) - 51 0 6-CI HH 4-CF3O-phenyl 52 0 6- CI H CH3-C (O) -4-CF3O-phenyl 53 0 6-CI HH 3-CH3-4-CI-phenyl 54 0 6-CI H (Cp3) 2CH-CH2- 3-CH3-4-CI-phenyl C (O) - 55 0 6-CI H 2-chloro-phenyl-C (O) -phenyl 56 0 6-CI H C2H5-OC (O) -phenyl (CH2) 2-C (O) -57 0 6-CI H NH2-C (O) - (CH2) 2- phenyl C (O) -20 58 0 6-CI H CH 3 C (O) -O- phenyl CH (CH 3) -C (O) -59 0 6-CI H CH 3 CH (OH) -C (O) -phenyl 60 0 6-CI H CH 3 C (O) -O-phenyl ( CH3) 2C-C (O) - 61 0 6-CI H (CH3) 2 (HO) CC (O) - phenyl 62 or 6-CI H CH3-C (O) -2-thienyl Ex. # R1 Q 63 0 6-CI H CH3-C (O) -2-furyl 64 0 6-CI HH 3-pyridyl 65 0 6-CI H CH 3 -C (O) -3-pyridyl 66 0 6-CI HH 4-pyridyl • 67 0 6-CI H CH 3 -C (O) -4-pyridyl 68 0 6-CI HH 4-CI-2-pyridyl 69 0 6-CI H CH 3 -C (O) -4-CI-2-pyridyl 70 0 6-CI HH 4-CH3-2-pyridyl 71 0 6-CI H CH3-C (O) - 4-CH3-2-pyridyl 72 0 6-CI H H 4-CH 3 O-2-pyridyl 73 0 6-CI H CH3-C (O) -4-CH3O-2-pyridyl 74 0 6-CI H (CH3) 2CH-CH2-C (O) 4-CH3O-2-pyridyl 75 or 6-CI H H 2-thiazolite 76 0 6-CI H CH3-C (O) -2-thiazolite 77 0 6-CI H H 2- (5-methylfuryl) 78 0 6-CI H CH3-C (O) -2- (5-methylfuryl) 79 0 6-CI HH 3-furyl • 10 80 or 6-CI H CH3-C (O) -3-furyl 81 0 6-CI HH 3-phenyl-5-isoxazolyl 82 0 6-CI H CH3-C ( O) - 3-phenyl-5-isoxazolyl 83 or 6-CI-CH 2- HH phenyl 84 0 6-CI -CH 2- H CH 3 -C (O) - phenyl 85 or 6-CI HH methyl 86 0 6- CI H CH3-C (O) -methyl 87 0 6-CI HH ethyl 88 or 6-CI H CH3-C (O) -ethyl 15 89 0 6-CI HH (CH3) 3C- 90 0 6-CI H CH3 -C (O) - (CH3) 3C- 91 0 6-CI H CH3-C (O) -2-pyrazinyl 92 or 6-CI H CH3-C (O) -2-naphthyl 93 0 6-CI HH cyclohexyl 94 0 6-CI H CH3-C (O) -cyclohexyl 95 0 6-CI H (Cp3) 2CH-CH 2 -cyclohexyl C (O) -96 0 5-nitro H CH 3 -C (O) -phenyl 97 0 5 -n¡tro H (Cp3) 2CH-CH2- 3-chlorophenol C (O) - 20 98 0 5-nitro H CH3-O-CH2-C (O) - 3-CH3-phenyl 99 0 5-amino H CH 3 -C (O) -phenyl 100 0 5-H 3 C- H CH 3 -C (O) -phenyl (O) 2S-NH-101 6-CF 3 H CH 3 -C (O) -phenyl HH 2- (6-CH 3 -pyridyl) 113 or 6-CI-H CH 3 -C (O) 2- (6-CH 3 -pyridyl) 114 0 6-CI-H 2 -tetrahydrofuryl-phenyl C (O) -115 or 6-CI - H (CH 3 O) (CH 3) C- phenyl C (O) - 10 116 0 6-CI - H CF 3 -CH 2 -C (O) -phenyl • 117 0 6-CI - H cyclopropyl-CH2- phenyl C (O) - 118 0 6-CI - H (CH2) 2 (HO) C-CH2- phenyl C (O) - 119 0 6-CI - H CH3S -CH2-C (O) - phenyl 120 0 6-CI-H CH3-S (O) -CH2- phenyl C (O) -121 0 6-CI-H CH3-S (O) 2-CH2-phenyl C (O) - 122 0 6-CI-CH 2 - H (CH 3) 2 N -CH 2 -C (O) -phenyl 15 123 0 5,6- -CH 2 - H CH 3 -C (O) - phenyl di methoxy 124 0 6 -CI - H CH 3 -C (O) -1-CH 3 -imidazol-2-yl 125 0 6-CI-HH 2-pyridyl H 126 or 6-CI-H CH 3 -C (O) -2-pyridyl 0 6-CI - HH 3-cyano-phenyl 128 0 6-CI - HH 3-NH2-C (O) - phenyl 129 0 6-CI - H CH 3 -C (O) - 3-NH 2 -C (O) - phenyl 20 130 0 6-CI - H CH 3 -C (O) -3-cyano-phenyl 131 0 6-CI-HH 3-HO-C (O) -phenyl 132 0 6-CI - H CH 3 -C ( O) - 3-HO-C (O) phenyl 133 0 6-CI-HH 3-H 3 C-OC (O) -phenyl, or 0-6-CI-H CH 3 -C (O) -3-H 3 C-OC ( O) - phenyl 135 0 6-CI-H CH 3 -C (O) -3-NH 2 -phenyl Ex. # X R 1 R2 Q 136 0 6-CI CH 3 -C (O) -3-NH 2 -phenyl fc H ( hydrochloride) 137 0 6-CI H CH 3 -C (O) -3-CH 3 -C (O) -HN-phenyl 138 0 6-CI H CH 3 -C (O) -3-CH 3 -S (O) 2- HN-phenyl 139 0 6-CI H CH3-C (O) -3- (CH3) 2N-fe Nile 140 0 6-CI H CH3-C (O) -3- (CH3) 2N-phenyl (hydrochloride) 141 or 6-CI H CH3-C (O) - 3,4- (HO) 2-phenyl 142 0 6-CI HH 3-NH 2 -S (O) 2-phenyl 143 0 6-CI H CH 3 -C (O) -3-NH 2 -S (O) 2-phenyl 144 0 6-CI HH 3-CH 3 -cyclohexyl 145 0 6-CI H CH3-C (O) - 3-CH3-cyclohexyl 146 0 6-CI CH3 CH3-C (O) - phenyl 147 0 6-CI CH3 CH3-C (O) - 3-CH3-cyclohexyl 148 0 6-CI CH3 CH3-C (O) -3-chlorophenyl 149 0 6-CI CH3 CH3-C (O) - cyclohexyl 150 0 6-CI HO2C- CH3-C (O) - phenyl CH2 151 0 6-CI CH3 CH3 phenyl 152 0 6-nitro H CH3-C (O) -phenyl 153 0 6-amino H CH3-C (O) - phenyl 154 or 5-CH3O H CH3-C (O) -phenyl 155 0 6-CH3O H CH3-C (O) -phenyl 156 0 5-FH CH3-C (O) -phenyl 157 0 6-CI H ( CH3) 3C-CH2-C (O) - phenyl 158 or 6-CI H 2 -bromophenyl-C (O) -phenyl 159 0 6-CI H 3-bromophenyl-C (O) -phenyl 160 0 6-CI H bromomethyl-C (O) -phenyl 161 0 6-CI H 4-bromophenyl-C (O) -phenyl 162 or 6-CI H C16H33-C (O) -phenyl 163 0 6-CI H CnH23-C (O) - phenyl 164 0 6-CI H 3,4-dichlorophenyl phenyl C (O) - 165 0 6-CI H 3,5-dichlorophenyl phenyl C (O) - 166 0 6-CI H C6H19-C (O) - phenyl 167 0 6-CI H 2 -furyl-C (O) -phenyl 168 0 6-CI H 4-fluorophenyl-C (O) -phenyl 169 0 6-CI H 2-iodophenyl-C (O) -phenyl 170 or 6-CI H C3F7-C (O) -phenyl 171 0 6-CI H 4-CF 3 -phenyl-C (O) -phenyl 172 0 6-CI H 4-methylphenyl-S (O) 2-N- phenyl CH (benzyl) - > «.

Eg # Y R1 R Q 173 or 6-CI H C5H? C (O) - phenyl 174 0 6-CI H C7H15-C (O> phenyl 175 0 6-CI H (C4H9) CH (C2H5-phenyl C (T ^ 176 or 6-CI H 3-fluorophenyl-C ( O) - phenyl 177 0 6-CI H C 16 H 13 -C (O) -phenyl 178 0 6-CI H phenoxymethyl-C (O) -phenyl 179 0 6-CI H (C 3 H 7) 2 CH-C (O) -phenyl 0 6-CI H phenyl-CH = CH-C (O) -phenyl 181 or 6-CI H phenylmethyl-C (O) -phenyl 182 0 6-CI H 4-CH 3 O -phenyl-C (O) -phenyl 0 6-CI H CH3S- (CH2) 2-C (O) -phenyl 184 0 6-CI H 2 -CH 3 O -phenyl-C (O) -phenyl 185 0 6-CI H C15F31-C (O) -phenyl 186 0 6-CI H (phenoxy) (CH 3) CH- phenyl C (O) - 187 0 6-CI H CH 2 = C (CH 3) -C (O) - phenyl 188 0 6-CI H 3,5-dinitrophenyl - phenyl C (O) - 189 0 6-CI H phenyl-CHCl-C (O) -phenyl 190 0 6-CI H (CH 3) 3 C-phenyl-C (O) -phenyl 191 0 6-CI H CH2CI- (CH2) 3-C (O) -phenyl 192 or 6-CI H (CH3) BrCH-C (O) -phenyl 193 0 6-CI H 4-nitro-2-chlorophenyl-phenyl C (O) -194 0 6-CI H 4-chloromethylphenyl-phenyl C (O) -190 0 6-CI H CH 2 Cl -CH 2 -C (O) -phenyl 196 0 6-CI H trans-CH 3 -CH = CH 2 -phenyl C (O) - 197 0 6-CI H (CH3) CHCl-C (O) - phenyl 198 or 6-CI H CH2CI- (CH2) 2-C (O ) - phenyl 199 0 6-CI H (CH 3) 2 C (CH 2 Cl) -phenyl C (O) - 200 0 6-CI H CH 2 -CH- (CH 2) β-phenyl C (O) - 201 0 6-CI H C10H21-C (O) -phenyl 202 0 6-CI H 4-cyanophenyl-C (O) -phenyl 203 0 6-CI H 4-CI-phenyloxymethyl-phenyl C (O) -204 0 6-CI H 4- CI-phenyl-C (O) -phenyl 205 0 6-CI H C8H17-C (O) -phenyl 206 0 6-CI H 3-nitrophenyl-C (O) -phenyl 207 0 6-CI H pentafluorophenyl-phenyl C (O) - 208 or 6-CI H CCI3-C (O) -phenyl 209 6-CI H 2 -nitrophenoxymethyl-phenyl C (O)-210 0 6-CI H 4-nitrophenyl-C (O) -phenyl 211 0 6-CI H l-naphthyl-C (O) -phenyl 212 0 6-CI H 2 -naphthyl-C (O) -phenyl 213 0 6-CI H 1 -naphthyl-S (O) 2-N-phenyl CH (benzyl) -C (O) - 214 6-CI H N-CH (benzyl) -phenyl C (O) -215 0 6-CI H C 17 H 33 -C (O) -phenyl 216 0 6-CI H C 2 H 5 O- C (O) - (CH2) 3- phenyl C (O) - 217 0 6-CI H 2-CF 3 -phenyl-C (O) -phenyl 218 0 6-CI H 3-CF 3 -phenyl-C (O) - phenyl 219 0 6-CI H 2,4,6-trichlorophenyl-phenyl C (O) -220 0 6-CI H 3 -CH 3 -phenyl-C (O) -phenyl • 221 0 6-CI H 4-CH 3 -phenyl-C (O) -phenyl 222 0 6-CI H 2 -CH 3 -phenyl-C (O) -phenyl 223 0 6-CI H C13H27-C (O) - phenyl 224 0 6-CI H (CH3) 3C-CH2- phenyl CH (CH3) -CH2-C (O) - 225 or 6-CI H 4-phenyl-phenyl-C (O) -phenyl 226 0 6- CI H (CH3) 2C = CH-C (O) - phenyl 227 0 6-CI H 5-CF3-3-phenyl-C (O) -phenyl 228 0 6-CI H 3-CF3-2-phenyl-C (O) - phenyl 229 0 6-CI H 2,4-diCF3-phenyl-phenyl C (O) - 15 230 0 6-CI H 2 -FC3-4-F-phenyl-phenyl C (O) -231 0 6-CI H 3,4,5-triF-phenyl-C (O) -phenyl 232 0 6-CI H CHF 2 - (CF 2) 3-C (O) -phenyl 233 0 6-CI H 2-chlorophenylmethyl- • phenyl C (O) - 234 0 6-CI H 3-CF3-4-F-phenyl-phenyl C (O) - 235 0 6-CI H 3,5-diCH 3 O-phenyl-phenyl C (O) - 236 0 6-CI H 2,4-difluorophenyl phenyl C (O) - 237 0 6-CI H (C2H5) (CH3) CH- phenyl C (O) - 238 0 6-CI H C2p5-CH- CH-CH2- phenyl CH = CH-CH2- CH = CH - (CH2) 7- C (O) - 242 0 6-CI H CH3CH2C (NO2) (CH3 phenyl) - (CH2) 2-C (O) - 243 0 6-CI H CI2C = CHCI-C (O) - phenyl 244 0 6-CI H 2,4f6-trifluorophenyl-phenyl-f-iP) - 245 6-CI H -f-CI-6-F-phenyl) -5-phenyl methaloxysol-4-yl-C (O ) - 246 6-CI H 5-CF3-2-F-phenyl-phenyl C (O) -247 or 6-CI H 4-nitro-2-furyl-C (O) -phenyl 248 0 6-CI H (phenoxy) (et? L) CH-phenyl • 10 C (O) - 249 0 6-CI H CH2CI- (CH2) 4-C (O) phenyl 250 0 6-CI H 2 -ethoxy-1 -naphthyl phenyl 251 0 6-CI H 2-chloro-3-pihdyl-phenyl C (O) -252 6-CI H 3- (2,6-di-C-phenyl) -5-phenyl methyl isoxaxol-4-yl-C (O) - 253 6-CI H 4-CF3-2-F-phenyl-phenyl C (O) - 254 0 6-CI H 3-CF 3 O -phenyl-C (O) phenyl 255 0 6-CI H (C3H7) (CH3) CH- phenyl C (O) - 256 0 6-CI H CH3O-C (O) - (CH2) 4- phenyl C (O) - 257 0 6-CI H (C2H5) (phenyl) CH- phenyl C (O) -258 or 6-CI H 3- (2-CI-phenyl) -5- phenyl methyl isoxaxol-4-yl- C (O) - 259 0 6-CI H 4-chlorophenyl-methyl-phenyl C (O) -20 260 0 6-CI H 4 -CH 3 -phenyl-chlorophenyl-methyl-C (O) -261 0 6-CI H 1 -CH 3 -cyclohexyl-phenyl C (O) -262 or 6-CI H (CH2Br) - (CH2) 2- phenyl C (O) - Ex. # X R1 Q 263 6-CI H CH3O-C (O) - (CH2) 2- phenyl C (O) - 264 0 6-CI H 3,4,5-tri (CH 3 O) - phenyl phenyl-C (O) - 265 0 6-CI H CH 3 O -C (O) - (CH 2) 3- phenyl C (O) - 266 0 6 -CI H 2,3,4-triF-phenyl-C (O) -phenyl 267 0 6-CI H 3-nitro-4-CI-phenyl-phenyl C (O) - 268 0 6-CI H 4-C3H7 -phenyl-C (O) -phenyl 269 0 6-CI H CH3-C (O) -O-phenyl CH (phenyl) -C (O)-270 0 6-CI H CH2CI-CHCI-C (O) - phenyl 271 0 6-CI H (CH2Br) - (CH2) 3- phenyl C (O) - 272 0 6-CI H 4-CH3O-phenylmethylphenyl C (O) - 273 0 6-CI H phenyl-CH2O- CH2- phenyl • 10 C (O) - 274 0 6-CI H 2 -thienylmethyl-C (O) - phenyl 275 0 6-CI H 2,3-di-F-phenyl-C (O) -phenyl 276 0 6-CI H 2,5-di-F-phenyl-C (O) -phenyl 277 or 6-CI H (CH 2 Br) - (CH 2) 4- phenyl C (O)-278 or 6-CI H 3,4-di ( CH3O) -phenyl-phenyl C (O) - 279 0 6-CI H cyclobutyl-C (O) -phenyl 280 0 6-CI H 3 -CH 3 O -phenyl-C (O) -phenyl 281 0 6-CI H 2,6-di-F-phenyl-C (O) - phen i lo 282 0 6-CI H (CH2Br) -CH2-C (O) -phenyl 283 0 6-CI H 2 , 3,6-triF-phenyl-C (O) -phenyl 284 0 6-CI H 3-CHCI2-phenyl-C (O) -phenyl 285 0 6-CI H cyclopentylethyl-C (O) -phenyl • 286 or 6-CI H 4-butylphenyl-C (O) -phenyl 287 0 6-CI H 2 -CH 3 C (O) O-phenyl-phenyl C (O) -288 0 6-CI H 3-CICH 2 -phenyl -C (O) - phenyl 289 0 6-CI H 2 -nitro-phenyl-C (O) -phenyl 290 0 6-CI H 3,5-diF-phenyl-C (O) -phenyl 291 0 6-CI H 3,4-di (CH 3 O) phenylphenol or methyl-C (O) -292 0 6-CI H (phenyl) 2CH-C (O) -phenyl 293 0 6-CI H 3,5- (CF 3) 2-phenyl-phenyl C (O) -294 0 6-CI H 2,4-diCI-5-F-phenyl-phenyl C (O) -295 or 6-CI H 3-methoxyphenylmethyl - C (O) phenyl - * .a Q Ex. # X R1 329 or 6-CI H 5-tert-butyl-2-methyl-pyrrazol-3-yl-C (0) -phenyl 330 or 6-CI H 2,3- (CH 3) 2-phenyl-C (0) -phenyl 331 or 6-CI H 2 -CL-4-F-phenyl-C (0) - Phenyl 332 or 6-CI H 4-Br-2-ethyl-5-methyl-pyrazol-3-yl-C (0) - Phenyl 333 or 6-CI H 4-methyl-1, 2,3-thiadiazol-5-yl Phenyl 334 or 6-CI H 5-methyl-3-phenyl-isoazol-4-yl-C (0) - Phenyl 335 or 6-CI H 2-chloro-5-pyridyl-C (0) - Phenyl 336 or 6-CI H 2 -benzyl-5-tert-bu.-l-pyrazol-3-l-C (0) - Phenyl 337 or 6-CI H 2-chloro-3-methoxy-4-thienyl-C (0) - Phenyl 338 or 6-CI H 3-chloro-4- (CH 2 -S (0) 2-) 2-thienyl-C (0) - Phenyl 339 or 6-CI H 1- (4-CI-phenyl) -5-CF3-pyrazol-4-yl-C (0) - Phenyl 340 or 6-CI H 5-methylisoxazol-3-yl-C (0) - Phenyl 341 or 6-CI H 3-chloro-2-thienyl-C (0) - Phenyl 342 or 6-CI H CHF2-CF2-C (0) - Phenyl 343 or 6-CI H CCIF2-CFCI-CF2-C (0) - Phenyl 344 or 6-CI H CHF2- (CF2) 7-C (0) - Phenyl 345 or 6-CI H CCIF2-CF2-C (0) - Phenyl 346 or 6-CI H 1- (4-CI-phenyl) -5-propylpyrazol-4-yl-C (0) - Phenyl 347 or 6-CI H trans-3-CF3-phenyl-CH = CH-C (0) - Phenyl 348 or 6-CI H 4-C5F110-phenyl-C (0) - Phenyl 349 or 6-CI H 4-C7F150-phenyl-C (0) - Phenyl 350 or 6-CI H 2,5-diCI-3-thienyl-C (0) - Phenyl 351 or 6-CI H 3-cyano-phenyl-C (0) - Phenyl 352 or 6-CI H iodoacetyl-C (O) - Phenyl 353 or 6-CI H 2,3-di-CI-5-p¡pdil-C (0) - Phenyl 354 or 6-CI H HOC (0) - (CH2) 2-C (0) - Phenyl 355 or 6-CI H CH3-C (0) -CH2-C (0) - Phenyl 356 or 6-CI H CH3CH (OH) -CH2-C (0) - Phenyl 357 or 6-CI H (CH3) 3C-CH2-C (0) -3-furyl 358 or 6-CI H C2H5-C (0) - 4-chloro-2-pyridyl 359 or 6-CI H (CH3) 2C-CH2-C (0) - 4-chloro-2-pyridyl 360 or 6-CI H CH3-C (0) -0- (CH3) 2C-C (0) -4-chloro-2-pyridyl 361 or 6-CI H (CH3) 2C (OH) -C (0) - 4-chloro-2-pyridyl 362 or 6-CI H CH3-C (0) -0- (CH3) CH-C (0) -4-chloro-2-pyridyl 363 or 6-CI H CH3CH (OH) -C (0) - 4-chloro-2-pipdyl 364 or 6-CI • CH3 CH3-C (O) - 4-chloro-2-pyridyl 365 or 6-CI - CH3 C2H5-C (0) - 3-chloro-phenyl 366 or 6-CI H CH3-C (0) - 5-pyrimidyl 367 or 6-CI H H 3-methyl-2-pyridyl 368 or 6-CI H CH3-C (0) - 3-methyl-2-pyridyl 369 or 6-CI H (CH3) 2CH-CH2-C (0) - 3-methyl-2-pyridyl 370 or H 4-hydroxymethyl-2-6-CI CH3C (0) - pyridyl 371 or 6-CI H C2H5-C (0) - 4-amino-2-pyridyl (hydrochloride) 372 or H 3-hydroxymethyl-2-6-CI CH3-C (0) - furyl 373 or H 3-hydroxymethyl-2-6-CI (CH3) 2CH-CH2-C (0) - furyl 374 or 4-hydroxymethyl-2-6-CI H C2H5-C (0) - furyl 375 or 4-hydroxymethyl-2-6-CI H (CH3) CH (CH) -C (0) - furyl Ex. # Y R2 Q 376 or 6-CI HH 5-methyl-2-thiazoyl 377 or 6-CI H (CH3) 2C-CH2-C (0) -5-methyl-2-thiazoyl 378 or 6-CI H CH3-C (0) -5-methyl-2-thiazoyl 379 or 6-CI H CH3-C ( 0) - 1 -methyl-3-pyrrolyl • 380 or 6-CI H (AcO) (CH3) 2C-C (0) -4-methyl-2-pyridyl 381 or 6-CI H (HO) (CH3) 2c-C (0) -4-methyl- 2-pyridyl 382 or 6-CI H (S) - (AcO) CH (CH 3) -C (0) -4-methyl-2-pyridyl 383 or 6-CI H (S) - (HO) CH ( CH3) -C (0) -4-methyl-2-pyridyl 384 or 6-CI H CH2CI-C (0) -4-methyl-2-pyridyl 385 or 6-CI H (CH3) 2N-CH2-C ( 0) - 4-methyl-2-pyridyl 386 or 6-CI H CH2CI-CH2-C (0) -4-methyl-2-pyridyl 387 or 6-CI H (CH3) 2N- (CH2) 2- C (0) - 4-Methyl-2-pyridyl 388 or 6-CI H Isopropyl-C (O) -3-HO-methyl-2-furyl 389 or 6-CI H ethyl-C (O) -2-HN2 -5-CI-phenyl 390 or 6-CI H ethyl-C (O) -2-HN2-5-CI-phenyl (hydrochloride) 2-acetylamino-5-CI-391 or 6-CI H ethyl-C (O ) - phenyl 3-HO-methyl-2- • 0 392 or 6-CI H ethyl-C (O) -pyridyl 393 or 6-CI H methyl-C (O) -phenyl •

Claims (11)

1. - A compound of the following formula: (O and the pharmaceutically acceptable salts thereof, wherein L is oxygen or sulfur, Y is a direct bond or an alkylidene C? -; Q is (a) alkyl C-? 6 or alkyl C-? 6 halosubstituted , said alkyl being optionally substituted with up to three substituents independently selected from hydroxy, C 1 alkoxy, amine and mono- or di- (C 1 .4 alkylamino), (b) C 3-7 cycloalkyl optionally substituted with up to three substituents independently selected from hydroxy, C 1 -C 4 alkyl, (c) phenyl or naphthyl, said phenyl or naphthyl being optionally substituted with up to four substituents independently selected from (c-1) halo, C 1 -C alkyl, halo-substituted, hydroxy, C alkoxy , alkoxy CM halosubstituted, S (O) mR3, SO2NH2, SO2 N (C-alkyl) 2, amino, mono- or di- (alkyl C? 4) amino, NHSO2R3, NHC (O) R3, CN, CO2H, CO2 (alkyl CM), alkyl C -OH, alkyl d.4-OR3, CONH2, CONH (C alquilo4 alkyl), CON (C? _4) 2 alkyl and OY-phenyl, said faith being nyl optionally substituted with one or two substituents independently selected from halo, alkylCM, CF3, hydroxy, OR3, S (O) mR3, amino, mono- or di- (C C4 alkyl) amino and CN, (d) a group 5-atom monocyclic aromatic, said aromatic group having a heteroatom selected from O, S and N and optionally containing up to three N atoms in addition to said heteroatom, and said aromatic group being substituted with up to three substituents independently selected from (d-1) ) halo, C 1 -alkyl, halo-substituted alkyl, hydroxy, alkoxy CM, halosubstituted alkoxy CM, alkyl CM-OH, S (O) mR 3, SO 2 NH 2, SO 2 N (alkyl d 4) 2, amino, mono- or di- (alkyl C) ? _4) amine, NHSO2R3, NHC (O) R3, CN, CO2H, CO2 (alkyl CM), alkyl CM-OR3, CONH2, CONH (alkyl CM), CON (alkyl d_4) 2, phenyl and phenyl mono -, di- or tri-substituted, wherein the substituent is independently selected from halo, CF3, alkylCM, hydroxy, C1-alkoxy. 4, OCF3, SR3, SO2CH3, SO2NH2, amino, alkylamine d-4 and NHSO2R3, (e) a monocyclic aromatic group of 6 atoms, said aromatic group having a heteroatom which is N and optionally containing up to three atoms in addition to said heteroatom , and said aromatic group being substituted with up to three substituents independently selected from the above group (d-1); R1 is hydrogen or d6 alkyl optionally substituted with a substituent independently selected from hydroxy, OR3, nitro, amino-mono- or di- (alkyld.) Amino, CO2H, CO2 (d4 alkyl), CONH, CONH (d4 alkyl) ) and CON (alkyl d.4) 2; R2 is (a) hydrogen, (b) alkyl d_4, (c) C (O) R5, wherein R5 is selected from (c-1) C? _22 alkyl or C2.22 alkenyl, said alkyl or alkenyl being optionally substituted with up to four substituents independently selected from (c-1-1) halo, hydroxy, OR3, S (0) mR3, nitro, amino, mono- or di- (alkyld4) amino, NHSO2R3, C02H, CO2 (C? .4 alkyl), CONH2, CONH (alkyl d) -4), CON (alkyl d.4) 2, OC (O) R3, thienyl, naphthyl and the groups of the following formulas: (c-2) C? _22 alkyl or C2.22 alkenyl, said alkyl or alkenyl being optionally substituted with five to forty-five halogen atoms, (c-3) -Y-cycloalkyl C3. or -Y-cycloalkenyl C3.7, said cycloalkyl or cycloalkenyl being optionally substituted with up to three substituents independently selected from (c-3-1) alkyl d_, hydroxy, OR3, S (O) mR3, amino, mono- or di- (alkyl d-4) amine, CONH2, CONH (alkyl d.4) and CON (C4-4) alkyl, (c-4) phenyl or naphthyl, said phenyl or naphthyl being optionally substituted with up to seven selected substituents independently between (c-4-1) halo, C? _8 alkyl, alkyl d_-OH, hydroxy, C1-8 alkoxy, halo substituted d8 alkyl, CN, nitro, S (O) mR3, SO2 NH2, SO2 NH (alkyl CM), SO 2 N (C 1 -) alkyl, amino, alkylamino CM, di- (alkyl d 4) amino, CONH 2, CONH (C 1 alkyl) 2, OC (0) R 3 and phenyl optionally substituted with up to three substituents independently selected from halo, alkyl CM, hydroxy, OCH3, CF3, OCF3, CN, nitro, amino, mono- or di- (alkyl d.4,) amino, CO2H, CO2 (alkyl d_4) and CONH2. (c-5) a monocyclic aromatic group as defined in (d) and (e) above, said aromatic group being optionally substituted with up to three substituents independently selected from (c-5-1) halo, C-? 8 alkyl, alkyl Cu-OH, hydroxy, alkoxy C? _8, CF3, OCF3, CN, nitro, S (O) mR3, amino, mono-di- (alkyl d-4) amino, CONH2, CONH (C? ), CON (alkyl d_4) 2, CO2H and CO2 (alkyl CM), and -Y-phenyl, said phenyl being optionally substituted with up to three substituents independently selected from halogen, alkyl CM, hydroxy, alkoxy CM, CF3, OCF3, CN , nitro, S (O) mR3, amine, mono- or di- (alkyl d_) amino, CO2H, CO2 (alkyl CM), CONH2, CONH (C? _ alkyl) and CON (C? _4) alkyl 2, ( c-6) a group of the following formula: X is halo, alkyl CM, hydroxy, alkoxy CM, halosubstituted alkoxy, S (O) mR3, amino, mono- or di- (alkyl d4) amino, NHSO2R3, nitro, halosubstituted CM alkyl, CN, CO2H, CO2 (alkyl) CM), alkyl d-4-OH, alkyl CM-OR3, CONH2, CONH (alkyl CM) OR CON (alkyl d4) 2; R3 is alkyl or C halosubstituted alkyl; m is 0,, 1 or 2; n 3; p is 1, 2, 3, 4 or 5; q is 2 or 3; Z is oxygen, sulfur or NR * '1; and R 4 is hydrogen, C 1-6 alkyl, halo-substituted C 1-4 alkyl or -Y-phenyl, said phenyl being optionally substituted with up to two substituents independently selected from halo, C alkyl, hydroxy, alkoxy d, S (O) mR 3, amino, mono- or di- (alkyl d.4) amino, CF3, OCF3, CN and nitro; with the proviso that a group of the formula -Y-Q is not methyl or ethyl when X is hydrogen; L is oxygen; R1 is hydrogen; and R2 is acetyl. 2. A compound according to claim 1, wherein Y is a direct bond, methylene or ethylene; Q is (a) C6_6 alkyl or C6_6 alkyl substituted, said alkyl optionally substituted with up to two substituents independently selected from hydroxy, CM alkoxy, amino and mono- or di- (alkyl d4) amine, ( b) C3 cycloalkyl. optionally substituted with up to two substituents independently selected from hydroxy, alkyl CM and alkoxy d. (c) phenyl or naphthyl, said phenyl or naphtyl being optionally substituted with up to four substituents independently selected from (c-1) halo, CM alkyl, halo d.4) halo substituted, hydroxy, d 4 alkoxy, halo substituted C, S (O) mR3, SO2NH2, SO2 N (alkyl) CM) 2, amino, mono- or di- (alkyld4) amino, NHSO2R3, NHC (O) R3, CN, CO2H, CO2 (alkyl CM), alkyl d.4-OH, alkyl d.4-OR3, CONH2 , CONH (alkyl d_4) and CON (C _ 4 alkyl) 2, (d) a monocyclic aromatic group of 5 atoms, said aromatic group having a heteroatom selected from O, S and N and optionally containing an N atom in addition to said heteroatom, and said aromatic group being substituted with up to three substituents independently selected from (d-1) halo, alkyl d-4, alkyl d. halo-substituted, hydroxy, alkoxy CM, halosulfided alkoxy, S (O) mR3, SO2NH2, SO2N (alkyl d4) 2, amino, mono- or di- (alkylC?) amino, NHSO2R3, NHC (O) R3, CN, CO2H, CO2 (C? _4 alkyl), alkyl d-4-OH, alkyl d_4OR3, CONH2, CONH (alkyl CM), CON (C? _4 alkyl) 2, phenyl and mono-, di- or trisubstituted phenyl, wherein the substituent is independently selected from halo, CF3, alkylCM, hydroxy, alkoxyCM, OCF3, SR3, SO2CH3, SO2NH2, amino, mono- or di- (alkylC? .4) amino and NHSO2R3, (e) a group monocyclic aromatic • 10 of 6 atoms, said aromatic group having a heteroatom which is N and optionally containing one or two N atoms in addition to said heteroatom, and said aromatic group being substituted with up to three substituents independently selected from the above group (d-1) ); R1 is hydrogen or d_6 alkyl optionally substituted with a substituent 15 independently selected from hydroxy, OR3, nitro, amino, mono- or di- (alkyl d-4) amino, CO2H; R2 is (a) hydrogen, (b) alkyl d4, (c) C (O) R5, • where R5 is selected from (c-1) alkyl d-? or C2_? 7 alkenyl, said alkyl or alkenyl being optionally substituted with up to four substituents independently selected from (c-1-1) halo, hydroxy, 20 OR3, S (O) mR3, nitro, amine, mono- or di- (alkyl d.4) amine, NHSO2R3, CO2H, CO2 (alkyl d.4), CONH2, CONH (alquik) d.4) , CON (alkyl d4) 2, OC (O) R3, and the groups of the following formulas: (c-2) C? _7 alkyl or C2? 7 alkenyl, said alkyl or alkenyl being optionally substituted with five to twenty halogen atoms, (c-3) -Y- C3 cycloalkyl. or -Y-cycloalkenyl C3. wherein said cycloalkyl or cycloalkenyl is optionally substituted with a substituent independently selected from CM alkyl, hydroxy and OR3, (c-4) phenyl or naphthyl, Wherein said phenyl or naphthyl is optionally substituted with up to three substituents independently selected from halo, C alquilo ?. alquilo alkyl, alkyl d_-OH, hydroxy, C? _8 alkoxy, halo-substituted C? _8 alkyl, halo-substituted d-8 alkoxy, CN, nitro, amine and mono- or di- (alkyl d_) amino, (c-5) a monocyclic aromatic group as defined in (d) and (e) above, said

The aromatic group optionally substituted with up to three substituents independently selected from halo, d, alkyl, alkyl d-4-OH, hydroxy, C 1 -8 alkoxy, CF 3, OCF 3, CN, nitro, amino and mono- or di- ( alkyl d. 4) amino, (c-6) tetrahydrofuryl, tetrahydropyrrolyl, tetrahydrothienyl or 1-methyl-tetrahydropyrrolyl; X is halo, d-4 alkyl, hydroxyl, d-alkoxy, halo-substituted alkoxy, amino, mono- or di- (C 1 .4 alkylamino), NHSO 2 R 3, nitro, halo-substituted alkyl, CN or CO 2 H; and R3 is haloalkyl C-alkyl.

3. A compound according to claim 2, wherein L is oxygen; And it's a direct link or methylene; Q is (b) C3 cycloalkyl. optionally substituted with d 4 alkyl or d 4 alkoxy (c) phenyl or naphthyl, said phenyl or naphthyl being optionally substituted with up to three substituents independently selected from (c-1) halo, CM alkyl, halo-substituted f, hydroxy, alkoxy CM, alkoxy C halosubstituted, amino, mono od-5 (alkyl d.4) amino, CN, CO2H, and SR3, (d) a monocyclic aromatic group of 5 atoms, said aromatic group having a heteroatom selected from O, S and N and optionally containing an N atom in addition to said heteroatom, and said aromatic group being substituted with up to three substituents independently selected from (d-1) halo, alkylCM, C halosubstituted alkyl, hydroxy, d-alkoxy, halosu-substituted alkoxy, amino, mono- or di- (alkyl CM) amino and alkyl d-4-OH, (e) a monocyclic aromatic group having 6 atoms, said aromatic group having a heteroatom.y optionally containing an N atom in addition to said heteroatom, and said aromatic group being substituted with up to three substituents 15 independently selected from the previous group (d-1); R1 is hydrogen or C-alkyl; R2 is (a) hydrogen (c) C (O) R5, where R5 is selected from (c-1) C8_8 alkyl or C2_8 alkenyl, said alkynyl being optionally substituted with up to three substituents independently selected from (c-1) -1) halo, hydroxy, OR3, SOR3, nitro, amino, 20 mono- or di- (alkyl d_4) amino, NHSO2R3, CO2H, CO2 (alkyl d.4), CON H2, CONH (alkyl d_4), CON (alkyl CM) and OC (0) R3, (c-2) C.sub.8-8 alkyl or C.sub.2-8 alkenyl, said alkyl or alkenyl being optionally substituted with five to seventeen halogen atoms, (c-3) -Y-cycloalkyl C3_7 or -Y- cycloalkenyl C3. , said replacement being substituted with an " substituent " independently substituted between alkyl substituted with up to three between halo, alkyl d. 5-hydroxy, (c-5) heteroaryl selected from pyridyl, quinolyl, thienyl, tialolyl, pyrimidyl and indolyl, said heteroaryl optionally substituted with up to two substituents independently selected from halo, alkyl d, hydroxy, alkoxy CM and CF3, (c -6) tetrahydrofuryl or tetrahydrothienyl; X is halo, alkyl CM, hydroxy, alkoxy CM, amino, nitro or CN; and R3 is alkyl C? _3 or • 10 CF3.

4. A compound according to claim 3, wherein Y is a direct bond; Q is phenyl, cyclohexyl optionally substituted with methyl, ethyl or methoxy, or a monocyclic aromatic group selected from pyridyl, pyrazinyl, thienyl, furyl, thiazolyl, imidazolyl and pyrrolyl, said Phenyl or aromatic group optionally substituted with up to two substituents independently selected from halo, methyl, methoxy, amino and hydroxymethyl, R 1 is hydrogen or methyl; R 2 is (a) hydrogen, (c) C (O) R 5, wherein R 5 is selected from (c-1) C 1-6 alkyl optionally substituted with up to two substituents independently selected from hydroxy, OR 3, 20 SOR3, nitro, amine, mono- or di- (alkylCM) amino, NHS02R3, C02H, C02 (C-alkyl), CONH2, CONH (alkylCal), CON (alkyl d.4) 2, OC (0) R3 and phenyl, (c-2) trifluoromethyl or trichloromethyl, (c-3) cyclopropyl or cyclohexyl, (c-4) phenyl or halophenyl, (c-5) thienyl, (c-6) tetrahydrofuryl; X is chlorine, fluoro or cyano; and R3 is methyl, ethyl, propyl or CF3.

5. A compound according to claim 4, wherein Y is a direct bond; Q is phenyl, 3-methoxyphenyl, 3-methylphenyl, 2-chlorophenyl, 3-chlorophenyl, 3-bromophenyl, 2-pyridyl, 4-chloro-2-pyridyl, 4-methyl-2-pyridyl, 4-methoxy-2- pyridyl, 2-pyrazinyl, cyclohexyl, 3-methyl-cyclohexyl, 3-NH2-phenyl, 3-methylcyclohexyl, 3-hydroxymethyl-2-furyl or 3-fluorophenyl; R1 is hydrogen or methyl; R2 is hydrogen, CH3-C (0) -, (CH3) 2-C (0) -, phenyl-C (O) -, C2H5-C (0) -, C3H7-C (0) -, cyclohexyl -C (O) -, (CH3) 2-CH-CH2-C (0) -, cyclopropyl -C (O) -, CH3- 0 -CH2-C (0) - , 2-chlorophenyl-C (0) -, C2H5-0-C (0) -CH2-C (0) -, (CH3) 2-CH-C (0) -, 2-tetrahydrofuryl-C (O) - , (CH30) (CH3) CC (O) -, CF3-CH2-C (0) -, cyclopropyl-CH2- C (O) -, CH3S-CH2-C (0) -, (CH3) 2N-CH2- C (0) - or (CH 3) 2 C (OH) -C (0) -; x is 6-chloro, 6-fluoro, 6-cyano or 6-nitro; and n is 1.

6. A compound according to claim 1, selected from: 3-amino-2-benzoyl-6-chloroindole; 3-acetylamino-2-benzoyl-6-chloroindole; 2-benzoyl-6-chloro-3- (isobutyrylamino) ethylene; 3- (benzamido) -2-benzoyl-6-chloroindole; 2-benzoyl-6-chloro-3- (propionylamino) indol; 2-benzoyl-3- (butyrylamino) -6-chloroindole; 2-benzoyl-6-chloro-3- (cyclohexylcarboxamido) -indole; 2-benzoyl-6-chloro-3- (isovalerylamino) ethylene; 2-benzoyl-6-chloro-3- (cyclopropylcarboxamido) indole; 2-benzoyl-6-chloro-3- (methoxyacetylamino) ddol; 3-amino-6-chloro-2- (3-methoxybenzoyl) indole 3-acetylamino-6-chloro-2- (3-methoxybenzoyl) indole; 3-amino-6-chloro-2- (3-methylbenzoyl) indole; 3-Acetylamino-6-chloro-2- (3-methylbenzoyl) indole; 5-chloro-2- (3-methylbenzoyl) -3- (propionylamino) indol; 6-chloro-3- (methoxyacetylamino) -2- (3-methylbenzoyl) ethylene; 3-amino-6-chloro-2- (3-chlorobenzoyl) ddol; 3-acetylamino-6-chloro-2- (3-chlorobenzoyl) dol; 6-chloro-2- (3-chlorobenzoyl) -3- (propionylamino) indole; 10 3- (butyrylamino) -6-chloro-2 (3-chlorobenzoyl) ddol; 6-chloro-2- (3-chlorobenzoyl) -3- (isovalerylamino) indole; 6-chloro-2- (3-chlorobenzoyl) -3- (methoxyacetylamino) indole; 3-acetylamino-6-chloro-2- (3-fluorobenzoyl) indole; 3-amino-2- (3-bromobenzoyl) -6-chloroindole; 15-acetylamino-2- (3-bromobenzoyl) -6-chloroindole; 2-benzoyl-6-chloro-3- (2-chlorobenzamido) indole; • 2-benzoyl-6-chloro-3- [(3-ethoxycarbonyl) propionylamino] indole; (s) - (+) -2-benzoyl-6-chloro-3- [(2-hydroxypropionyl) amino] -indole; 3-amino-6-chloro-2- (4-chloropyridine-2-carbonyl) indole; 3-Acetylamino-6-chloro-2- (4-chloropyridine-2-carbonyl) ethylene; 3-amino-6-chloro-2- (4-methylpyridine-2-carbonyl) indole; 3-acetylamino-6-chloro-2- (4-methylpyridine-2-carbonyl) indole; 3-amino-6-chloro-2- (4-methoxypyridine-2-carbonyl) indole; 3-acetylamino-6-chloro-2- (4-methoxypyridine-2 * carbonyl) indole; 6-Chloro-3-isovalerylamino-2- (4-methoxypyridine-2-carbonyl) ddol; 3-acetylamino-6-chloro-2- (pyrazine-2-carbonyl) dol; 3-Acetylamino-6-chloro-2- (cyclohexanecarbonyl) ethylene; 5-acetylamino-2-benzoyl-6-fluoroindole; 3-acetylamino-2-benzoyl-6-cyanoindole; 2-benzoyl-6-chloro-3- [(2-tetrahydrofuryl) carboxamido] indole; 2-benzoyl-6-chloro-3- [(2-methoxypropionyl) aminol] indole; 2-benzoyl-6-chloro-3- (3,3,3-trifluoropropylamino) indole; • 10 2-benzoyl-6-chloro-3- (cyclopropaneacetylamino) indole; 2-benzoyl-6-chloro-3- (methylthoacetylamino) indole; 2-benzoyl-6-chloro-3- [(N, N-dimethylaminoacetyl) amino] ddol; 3-amino-6-chloro-2- (pyridine-2-carbonyl) indole; 3-acetylamino-6-chloro-2- (pyridine-2-carbonyl) indole; 3-Acetylamino-2- (3-aminobenzoyl) -6-chloroindole hydrochloride; 3-acetylamino-6-chloro-2- (3-methylcyclohexylcarbonyl) ddol; • 3- (N-Acetyl-N-methylamino) -6-chloro-2- (3-chlorobenzoyl) indole; 2-benzoyl-6-chloro-3- (N, N-d-methylammon) indole; 3-acetylamino-2-benzoyl-6-nitroindol; 3-Acetylamino-6-chloro-2- (3-hydroxymethyl-2-furoyl) indole; 6-chloro-2 - (4-chloropyridine-2-carbonyl) -3- (propionylamino) indole; 6-chloro-2 - (4-chloropyridine-2-carbonyl) -3- (2-hydroxyisobutyrylamino) ) indole; 3-acetylamino-6-chloro-2- [2- (5-methylalzo..f)? indole; 3- (2-acetoxyisobutyrylamino) -6 ^ .oro-2- (4-chloropyridine-2-carbonyl) ddol; 6-chloro -2- (4-chloropyridine-2-carbop) -3- (isovalerylamino) ddol; 6-chloro-2 - (4-chloropyridine fe-carbonyl) -3 - [[(S) -2-5-hydroxypropionyl] amino] indole; 3- (N-acetyl-N-methylamino) -6-chloro-2- (4-chloropyridine-2-carbonyl) indole; and 2- (4-aminopyridine-2-carbonyl) -6-chloro-3- (propynylamino) hydrochloride Ndol.

7. A compound according to claim 6, selected from: 3-acetylamino-2-benzoyl-6-chloroindole; 2-benzoyl-6-chloro-3- (isovalerylamino) ethylene; 3-Acetylamino-6-chloro-2- (3-methylbenzoyl) idol; 3-acetylamino-6-chloro-2- (3-chlorobenzoyl) ddol; 15 6-chloro-2- (3-chlorobenzoyl) -3- (propionylamino) indole; 3-acetylamino-6-chloro-2- (4-chloropyridine-2-carbonyl) indole; ^ 3-acetylamino-6-chloro-2- (4-methy1pyridine-2-carbonyl) ddol; 2-benzoyl-6-chloro-3- (methylthoacetylamino) ethylene; 6-chloro-2 - (4-chloropyridine-2-carbonyl) -3- (propionylamino) indole; 3-Acetylamino-6-chloro-2- (3-hydroxymethyl-2-furoyl) dol; 6-chloro-2 - (4-chloropyridine-2-carbonyl) -3- (2-hydroxyisobutyrylamino) ddol; and 3-acetylamino-6-chloro-2- [2- (5-methylthiazole)] dol;

8. - A compound according to claim 7 selected from: 3-acetylamino-2-benzoyl-6-chloroindole; 2-benzoyl-6-chloro-3- (isovalerylamino) indole; 3-Acetylamino-6-chloro-2- (3-methylbenzoyl) indole; 3-acetylamino-6-chloro-2- (3-chlorobenzoyl) ddol; 6-chloro-2- (3-chlorobenzoyl) -3- (propionylamino) indole; 3-acetylamino-6-chloro-2- (4-methylpyridine-2-carbonyl) indole; 2-benzoyl-6-chloro-3- (methylthioacetylamino) indole; • 10 6-chloro-2 - (4-chloropyridine-2-carbonyl) -3- (propynylamino) indole; and 6-chloro-2 - (4-chloropyridine-2-carbonyl) -3- (2-hydroxyisobutyrylamino) -dol.

9. A pharmaceutical composition useful for the treatment of a medical condition in which prostaglandins are implicated as 15 pathogens, which comprises a compound of the formula (I) of claim 1 and a pharmaceutically inert carrier.

10. A pharmaceutical composition useful for the treatment of a medical condition in which prostaglandins are implicated as pathogens, comprising a compound of the formula (I): (I) and the pharmaceutically acceptable salts thereof, wherein L is oxygen or sulfur; And it is a direct bond or an alkylidene d_4; Q is (a) halosubstituted C? -alkyl, said alkyl optionally substituted with up to three substituents independently selected from hydroxy, alkoxy, amino, and mono- or di- (alkyl d_4), amino, (b) cycloalkyl C3.7 optionally substituted with up to three substituents independently selected from hydroxy, Cu alkyl and Cu alkoxy, (c) phenyl or naphthyl, said phenyl or naphthyl being optionally substituted with up to four substituents independently selected from (c-1) halo, Cu alkyl, Cu alkyl , halo-substituted, hydroxy, halo-substituted alkoxy, S (0) mR3, S02NH2, S02N (alkylCou) 2, amine, mono- or di- (alkylCu) amino, NHS02R3, NHC (0) R3, CN, C02H, C02 ( alkyl Cu), alkyl d.4OH, alkyl Cu-OR3, CONH2, CONH (alkyl Cu), CON (alkyl Cu) 2 and OY-phenyl, said phenyl optionally substituted with one or two substituents independently selected from halo, alkyl Cu , CF3, hydroxy, OR3, S (O) mR3, amine, mono- or di- (alkyl) Cu) amino and CN, (d) a monocyclic aromatic group of 5 atoms having said aromatic group a heteroatom selected from O, S and N and optionally containing up to three N atoms in addition to said heteroatom, and said aromatic group being substituted with to three substituents independently selected from (d-1) halo, Cu alkyl, halo substituted Hal, hydroxy, Cu alkoxy, halo substituted Alkoxy, alkyl d_-OH, S (O) mR3, S02NH2, S02 N (alkyl d4) 2, amine, mono- or di- (alkyl Cu) amino, NHS02R3, NHC (0) R3, CN, C02H, C02 (alkyl Cu), alkyl Cu-OR3, CONH2, CONH (alkyl Cu), CON (alkyl CM) 2 , phenyl and phenyl mono-, di or tri-substituted, where the substituent is independently selected from halo, CF3, alkyl Cu, hydroxy, alkoxy Cu, OCF3, SR3, S02CH3, S02NH2, amino, alkylamino C? _4 and NHS02R3, ( e) a monocyclic aromatic group of 6 atoms, said aromatic group having a heteroatom which is N and optionally containing up to three volumes in addition to said heteroatom, and said aromatic group substituted with up to three substituents independently selected from the above group (d-1) wherein; R1 is hydrogen or d6 alkyl optionally substituted with a substituent independently selected from hydroxy, OR3, nitro, amino, mono- or di- (alkyl Cu) amino, C02H, C02 (alkyl Cu), CONH2, CONH (alkyl Cu), and CON (alkyl Cu) 2; R2 is (a) hydrogen, (b) alkyl Cu, (c) C (0) R5, wherein R5 selects from (c-1) d.22 alkyl or C2.22 alkenyl, said alkyl or alkenyl being optionally substituted with up to four substituents independently selected from (c-1-1) halo, hydroxy, OR3, S (O) mR3, nitro, amino, mono- or di- (alkyl Cu) amino, NHS02R3, C02H, C02 (alkyl Cu), CON H2, CONH (alkyl Cu), CON (alkyl Cu) 2, OC (0) R3, thienyl, naphthyl and the groups of the following formulas: (c-2) alkyl d.22 or alkengjp C2.22, said alkyl or alkenyl is cycloalkenyl or cycloalkenyl optionally substituted with up to three substituents independently selected from (c-3-1) alkyl Cu, hydroxy, OR3, S (O) mR3, amino, mono- or di- (alkyl Cu) amine, CONH2, CONH (alkyl) Cu) and CONH (CM alkyl) 2, (c-4) phenyl or naphthyl, said phenyl or naphthyl optionally substituted with up to seven substituents independently selected from (c-4-1) halo, alkyl d.8, alkyl Cu- OH, hydroxyl, C? -8 alkoxy, substituted d.sub.8 halo alkyl, haloalken d8 alkoxy, CN, nitro, S (O) mR3, S02NH2, S02NH (alkyl Cu), S02N (C) alkyl, amino, alkylamine Cu , di- (alkyl Cu) amino, CONH2, CONH (alkyl Cu), CON (alkyl d_) 2, OC (O) R3 and phenyl optionally substituted with up to three substituents independently selected from halo, alkylCM, hydroxy, OCH3, CF3 , OCF3, CN, nitro, amino, mono- or di- (alkyl d_4) amino, C02H, C02 (alkyl CM) and CONH2, (C-5) a monocyclic aromatic group as defined in (d) and (e) ant The aromatic group is optionally substituted with up to three substituents independently selected from (c-5-1) halo, alkyl d-8, alkyl d_-OH, hydroxy, alkoxy C-? -8, CF3, OCF3, CN, nitro , S (O) mR3, amino, mono- or di- (alkyl CM) amino, CONH2, CONH (alkyl Cu), CON (alkyl Cu) 2, C02H and C02 (alkyl C? _), And -Y-phenyl said phenyl being optionally substituted with up to three substituents independently selected from halogen, alkylCal, hydroxy, alkoxy Cu, CF3, OCF3, CN, nitro, & (0) mR3, amine, mono- or di- (alkyl Cu) amino, C02H, C02 (alkyl Cu), CONH2, CONH (alkyl Cu) and CON (alkyl d_) 2, (c-6) a group of the following formula: X is halo, alkyl Cu, hydroxy, alkoxy Cu, alkoxy Cu, halosubstituted, S (O) mR3, amino, mono- or di- (C4u alkyl) amine, NHS02R, nitro, alkyl d_4 halosubstituted, CN, C02H, C02 (alkyl Cu), alkyl Cu OH, alkyl Cu-OR 3, CONH 2, CONH (alkyl Cu) or CON (alkyl d 4) 2; R3 is alkyl d4 or haloalkyl substituted; m is 0, 1 or 2; n is 0, 1, 2 or 3; p is 1, 2, 3, 4 or 5; q is 2 or 3; z is oxygen, sulfur or NR4; and R 4 is hydrogen, C 1-6 alkyl, halo-substituted alkyl or -Y-phenyl, said phenyl being optionally substituted with up to two substituents independently selected from halo, alkyl Cu, hydroxy, alkoxy Cu, S (O) mR 3, amine, mono - or di- (alkyl Cu) amine, CF3, OCF3, CN and nitro; and a pharmaceutically inert vehicle.

11. A method for the treatment of a medical condition in which the prostaglandins are implicated as pathogens, in a mammalian subject, comprising administering said pharmaceutical composition according to claim 10. This invention provides a compound of the following formula: And pharmaceutically acceptable salts thereof, wherein L is oxygen or sulfur, Y is a direct bond or Cu alkylidene; Q is C 1-6 alkyl, C 3-7 cycloalkyl, phenyl, naphthyl, heteroaryl or the like; R1 is hydrogen, C-? 6 alkyl, or the like; R2 is hydrogen, alkylCal, C (O) R5 where R5 is alkyl d. 22, or C2.22 alkenyl, d-s alkyl, halo-substituted, C2_8 alkenyl, halo-substituted, -15 Y-C3.7 cycloalkyl, -C3.7-cycloalkenyl, phenyl, naphthyl, heteroaryl or the like; X is halo, alkyl Cu, hydroxy, alkoxy Cu or the like; and n is 0, 1, 2 or 3, with the proviso that a group of formula -Y-Q is not methyl or ethyl when X is hydrogen; L is oxygen; R1 is hydrogen; and R2 is acetyl; This invention also provides a pharmaceutical composition useful for the treatment of 20 a medical condition in which prostaglandins are implicated as pathogens. PF / all * P99 / 1807F : •* Y-