ES2523167T3 - Derivado de (aza)indol intermedio sustituido en la posición 5 - Google Patents

Derivado de (aza)indol intermedio sustituido en la posición 5 Download PDF

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ES2523167T3
ES2523167T3 ES11194457.5T ES11194457T ES2523167T3 ES 2523167 T3 ES2523167 T3 ES 2523167T3 ES 11194457 T ES11194457 T ES 11194457T ES 2523167 T3 ES2523167 T3 ES 2523167T3
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alkenyl
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Maria Alessandra Alisi
Guido Furlotti
Nicola Cazzolla
Caterina Maugeri
Patrizia Dragone
Barbara Garofalo
Isabella Coletta
Giorgina Mangano
Beatrice Garrone
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Angelini Acraf SpA
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Abstract

Compuesto intermedio de fórmula (III):**Fórmula** en la que G1, G2 y G3, que pueden ser idénticos o diferentes, son un átomo de nitrógeno o un grupo CH; R1 es un grupo alquilo (C1-C6), cicloalquilo (C3-C7), alquil (C1-C6)-ORI, (CH2)nCONRIIRIII, (CH2)nCORI, (CH2)nCOORII, (CH2)nOCORI, SO2RI, (CH2)nNRIISO2RI, (CH2)nSO2RI, opcionalmente sustituido con 1 a 3 grupos hidroxilo, en los que n es un entero de 1 a 6, RI es un grupo alquilo (C1-C3) o alquil (C1-C3)-OH, y RII y RIII, que pueden ser idénticos o diferentes, son un átomo de hidrógeno o un grupo alquilo (C1-C3); W es un enlace σ, o un grupo alquilo (C1-C6), alquenilo (C2-C6), O-alquilo (C1-C6), O-alquenilo (C2-C6), (CH2)pCO(CH2)q o (CH2)pC(OH)(CH2)q, en los que p y q, que pueden ser idénticos o diferentes, son un entero de 0 a 3; y R2 es un grupo fenilo o piridina, opcionalmente sustituido con de 1 a 3 sustituyentes, que pueden ser idénticos o diferentes, representados por un grupo L-M, en el que L es un enlace σ, o un grupo alquilo (C1-C6), alquenilo (C2- C6), alquinilo (C2-C6), O-alquilo (C1-C6), O-alquenilo (C2-C6), O-alquinilo (C2-C6), y M es un átomo de hidrógeno o de halógeno, o un grupo OH, CF3, NO2, COORII, SO2NHRII, CH2CONRIIRIII, NRIIRIII, SO2RIV, NHSO2RIV, PORIVRV u OPORIVRV, en los que RII y RIII, que pueden ser idénticos o diferentes, presentan el significado anterior, y RIV y RV, que pueden ser idénticos o diferentes, son un grupo alquilo (C1-C3), siempre que cuando G1, G2 y G3 son todos un grupo CH, R1 es un grupo alquilo (C1-C6) o cicloalquilo (C3-C7), opcionalmente sustituido con 1 a 3 grupos hidroxilo, W es un enlace σ, y el enlace entre los átomos de carbono en la posición 2 y 3 es un doble enlace, R2 no sea un grupo fenilo o piridina, opcionalmente sustituido con 1 a 3 sustituyentes, que pueden ser idénticos o diferentes, seleccionados de entre halógeno, alquilo (C1-C6) opcionalmente sustituido con un grupo hidroxilo, trifluorometilo, nitro, amino, di(alquil (C1-C3))amino, hidroxilo, alcoxilo (C1-C3), COOH, COORII, SO2CH3, SO2NHCH3, NHSO2CH3, PORIVRV, OPORIVRV, alquil (C1-C6)-COOH y alquenil (C2-C6)-COOH; y siempre que cuando G1 es N, y G2 y G3 son un grupo CH, R2 no sea un grupo aromático divalente sustituido con un grupo L-M representado por un grupo O-alquilo (C1-C6), O-alquenilo (C2-C6) y O-alquinilo (C2-C6).

Description

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imagen7
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TABLA 1
Compuesto
Fórmula estructural Ejemplo Purificación Masamonoisotópica CL/EM(M+H)+ 1 H-RMN (300 MHz)
1
imagen21 2(a) B (Hex/EtOAc; del90→40% dehex) 389,13 390,3 1 H-RMN (CDCl3 ): 8,41 (d, J= 2,4 Hz, 1H);8,32 (d, J= 2,4 Hz, 1H); 8,19 (s, 1H); 7,74 (m,1H); 7,50-7,20 (om, 7H); 6,42 (s, 1H); 4,34 (q,J= 7,2 Hz, 2H); 2,42 (s, 3H); 1,27 (t, J= 7,2Hz, 3H).
2
imagen22 2(a) B (Hex/ EtOAc= 8/2) 403,15 404,4 1 H-RMN (CDCl3 ): 8,405 (d, J= 2,4 Hz, 1H);8,30 (d, J= 2,4 Hz, 1H); 8,00 (s, 1H); 7,83 (m,1H); 7,50-7,20 (om, 7H); 6,37 (s, 1H); 4,67(ept. J = 6,9 Hz, 1H); 2,43 (s, 3H); 1,69 (d, J=6,9 Hz, 6H).
3
imagen23 2(a) B (Hex/ EtOAc= 6/4) 419,14 420,4 1 H-RMN (CDCl3 ): 8,45 (d, J= 2,1 Hz, 1H);8,34 (d, J= 2,1 Hz, 1H); 8,13 (s a, 1H); 7,79(m, 1H); 7,55-7,20 (om, 7H); 6,46 (s, 1H);4,49 (t, J= 6,0 Hz, 2H); 3,68 (t, J= 6,0 Hz, 2H);3,17 (s, 3H); 2,42 (s, 3H).
4
imagen24 2(a) B (Hex/ EtOAc= 6/4) 393,10 394,3 1 H-RMN (CDCl3 ): 8,47 (d, J=2,4 Hz, 1H); 8,33(d, J= 2,4 Hz, 1H): 8,07 (s, 1H); 7,78 (m, 1H);7,60-7,10 (2 m, 7H), 6,45 (s, 1H); 4,34 (q, J=6,9 Hz, 2H); 1,28 (t, J= 6,9 Hz 3H)
5
imagen25 2(a) B (Hex/EtOAc;del 70→60%de hex) 423,11 424,2 1 H-RMN (CDCl3 ): 8,44 (d, J = 2,1 Hz); 8,33 (d,J = 2,1 Hz); 8,10 (s a, 1H), 7,78 (m, 1H), 7,657,10 (3 m, 7H); 6,46 (s, 1H); 4,44 (t, J= 5,7Hz, 2H); 3,72 (t, J= 5,7 Hz, 2H); ); 3,18 (s,3H).
6
imagen26 2(a) B (Hex/ EtOAc= 6/4) 422,12 423,3 1 H-RMN (300 MHz, DMSO-d6 ) 3,07 (s, 3H) 3,54 (t, J=5,61 Hz, 2H) 4,31 (t, J=5,45 Hz, 2H) 6,52 (s, 1H) 7,29 - 7,69 (m, 10 H) 8,03 (d,J=1,65 Hz, 1H) 10,32 (s, 1H)
22 23 24 25 26 27
7
imagen27 2(a) B (Hex/EtOAcdel 100→70%) 460,13 461,7 1 H-RMN (300 MHz, DMSO-d6 ) 1,10 (t, J=7,27Hz, 3H) 1,80 (quin, J=7,10 Hz, 2H) 2,09 (t,J=7,10 Hz, 2H) 3,93 (q, J=7,27 Hz, 2H) 4,25(t, J=7,10 Hz, 2H) 6,54 (s, 1H) 7,38 -7,65 (m,11H) 8,06 (d, J=1,98 Hz, 1H) 10,33 (s, 1H)
8
imagen28 2(a) B (Hex/EtOAc; del100→60% dehex) 446,14 447,7 1 H-RMN (300 MHz, DMSO-d6 ) 1,05 (t, J=7,27Hz, 3H) 2,59 (t, J=7,27 Hz, 2H) 3,90 (q,J=7,27 Hz, 2H) 4,48 (t, J=7,27 Hz, 2H) 6,54(s, 1H) 7,38 -7,66 (m, 11H) 8,04 (d, J=1,98Hz, 1H) 10,33 (s, 1H)
9
imagen29 2(a) A (Hex/ EtOAc= 8/2) 417,16 418,7 1 H-RMN (300 MHz, DMSO-d6 ) 2,00 (s, 6H)2,41 (t, J=7,10 Hz, 2H) 4,26 (t, J=7,10 Hz, 2H)6,52 (s, 1H) 7,38 -7,63 (m, 11H) 8,04 (d,J=1,65 Hz, 1H) 10,32 (s, 1H)
10
imagen30 2(a) A (Hex/ EtOAc= 8/2) 380,17 381,6 1 H-RMN (300 MHz, DMSO-d6 ) 1,17 -1,57 (m,6H) 1,25 (t, J=7,10 Hz, 3H) 1,61 -1,87 (m,2H) 1,88 -2,06 (m, 2H) 2,61 -2,83 (m, 1H)4,16 (q, J=6,94 Hz, 2H) 6,17 (s, 1H) 7,26 7,38 (m, 2H) 7,39 -7,62 (m, 4 H) 7,88 (s, 1H)10,21 (s, 1H)
11
imagen31 2(a) B (Hex/EtOAc; del100→70% dehex) 432,12 433,8 1 H-RMN (300 MHz, DMSO-d6 ) 1,13 (t, J=7,10Hz, 3H) 4,09 (q, J=6,94 Hz, 2H) 5,00 (s, 2H)6,61 (s, 1H) 7,35-7,64 (m, 11H) 8,06 (s, 1H)10,35 (s, 1H)
12
imagen32 2(a) B (Hex/ EtOAc= 9/1) 404,13 405,6 1 H-RMN (300 MHz, DMSO-d6 ) 3,06 (s, 3H)3,54 (t, J=5,61 Hz, 2H) 4,34 (t, J=5,78 Hz, 2H)6,53 (s, 1H) 7,35 -7,68 (m, 11H) 8,03 (d,J=1,98 Hz, 1H) 10,32 (s, 1H)
13
imagen33 2(a) A (Hex/ EtOAc= 8/2) 446,14 447,2 1 H-RMN (300 MHz, DMSO-d6 ) 1,76 -1,93 (m,2H) 1,80 (s, 3H) 3,72 (t, J=5,94 Hz, 2H) 4,32(t, J=6,94 Hz, 2H) 6,54 (s, 1H) 7,38 -7,64 (m,11H) 8,05 (d, J=1,65 Hz, 1H) 10,33 (s, 1H)
14
imagen34 2(a) A (Hex/ EtOAc= 8/2) 432,12 433,4 1 H-RMN (300 MHz, DMSO-d6 ) 1,73 (s, 3H)4,15 (t, J=5,28 Hz, 2H) 4,47 (t, J=5,28 Hz, 2H)6,54 (s, 1H) 7,37 -7,66 (m, 11H) 8,05 (d,J=1,65 Hz, 1H) 10,34 (s, 1H)
15
imagen35 2(a) B (Hex/ EtOAc= 7/3) 416,13 417,3 1 H-RMN (300 MHz, DMSO-d6 ) 1,99 (s, 3H)2,82 (t, J=7,43 Hz, 2H) 4,37 (t, J=7,43 Hz, 2H)6,54 (s, 1H) 7,24 -7,74 (m, 11H) 8,05 (d,J=1,32 Hz, 1H) 10,33 (s, 1H)
16
imagen36 2(f) C (CH3 CN/ H2 O+el 0,1%de HCOOH,del 30→65%,15 minutos) 438,08 439,5 1 H-RMN (300 MHz, DMSO-d6 ) 2,37 (s, 3H)3,01 (s, 3H) 6,87 (s, 1H) 7,24 (d, J=7,60 Hz,2H) 7,39 -7,65 (m, 7 H) 7,92 (d, J=8,92 Hz,1H) 8,18 (d, J=1,65 Hz, 1H) 10,60 (s, 1H)
17
imagen37 2(f) C (CH3 CN/ H2 O+el 0,1%de HCOOH,del 30→65%,15 minutos) 424,06 425,2 1 H-RMN (300 MHz, DMSO-d6 ) 3,04 (s, 3H)6,92 (s, 1H) 7,39 -7,64 (m, 10 H) 7,92 (d,J=9,08 Hz, 1H) 8,19 (d, J=1,98 Hz, 1H) 10,60(s, 1H)
18
imagen38 2(f) C (CH3 CN/H2 O+el 0,1% deHCOOH, del30→65%, 15minutos) 430,11 431,4 1 H-RMN (300 MHz, DMSO-d6 ) 1,16 -1,51 (m,5H) 1,60 -1,90 (m, 3H) 2,10 (d, J=7,76 Hz,2H) 3,04 -3,19 (m, 1H) 3,21 (s, 3H) 6,66 (s,1H) 7,42 -7,61 (m, 5H) 7,83 (d, J=9,25 Hz,1H) 8,04 (d, J=1,98 Hz, 1H) 10,51 (s, 1H)
19
imagen39 2(f) C (CH3 CN/ H2 O+ el 0,1%de HCOOH,del 30→65%,15 minutos) 425,06 426,4 1 H-RMN (300 MHz, DMSO-d6 ) 3,79 (s, 3H)7,10 (s, 1H) 7,35 -7,66 (m, 6H) 7,76 (d,J=7,76 Hz, 1H) 7,86 -8,04 (m, 2H) 8,22 (d,J=1,82 Hz, 1H) 8,69 (ddd, J=4,87, 1,73, 0,83Hz, 1H) 10,59 (s, 1H)
20
imagen40 2(f) C (CH3 CN/ H2 O+ el 0,1%de HCOOH,del 30→65%,15 minutos) 449,06 450,3 1 H-RMN (300 MHz, DMSO-d6 ) 3,08 (s, 3H)7,10 (s, 1H) 7,36 -7,69 (m, 5H) 7,74 -7,82(m, 2H) 7,86 -7,97 (m, 3H) 8,23 (d, J=1,98Hz, 1H) 10,64 (s, 1H)
21
imagen41 2(f) C (CH3 CN/ H2 O+el 0,1%de HCOOH,del 30→65%,15 minutos) 452,10 453,4 1 H-RMN (300 MHz, DMSO-d6 ) 2,95 -3,10 (m,2H) 3,22 (t, J=7,76 Hz, 2H) 3,27 (s, 3H) 6,69(s, 1H) 7,16 -7,26 (m, J=8,48, 4,38, 4,22,4,22 Hz, 1H) 7,31 (d, J=4,46 Hz, 4 H) 7,40 7,64 (m, 5H) 7,84 (d, J=8,92 Hz, 1H) 8,05 (t,J=1,57 Hz, 1H) 10,52 (s, 1H)
22
imagen42 2(f) C (CH3 CN/ H2 O+el 0,1%de HCOOH,del 30→65%,15 minutos) 492,05 493,4 1 H-RMN (300 MHz, DMSO-d6 ) 3,06 (s, 3H)7,09 (s, 1H) 7,40 -7,73 (m, 6H) 7,75 -7,82(m, 1H) 7,85 -8,00 (m, 3H) 8,22 (d, J=1,65Hz, 1H) 10,63 (s, 1H)
23
imagen43 2(f) C (CH3 CN/ H2 O+el 0,1%de HCOOH,del 30→65%,15 minutos) 458,03 459,5 1 H-RMN (300 MHz, DMSO-d6 ) 3,05 (s, 3H)6,97 (s, 1H) 7,40 -7,70 (m, 9 H) 7,92 (d,J=9,08 Hz, 1H) 8,20 (d, J=1,82 Hz, 1H) 10,62(s, 1H)
24
imagen44 2(f) C (CH3 CN/ H2 O+el 0,1%de HCOOH,del 30→65%,15 minutos) 463,08 464,4 1 H-RMN (300 MHz, DMSO-d6 ) 3,05 (s, 3H)4,12 (s, 2H) 6,94 (s, 1H) 7,33 -7,72 (m, 9H)7,92 (d, J=8,92 Hz, 1H) 8,19 (d, J=1,65 Hz,1H) 10,61 (s, 1H)
25
imagen45 2(f) C (CH3 CN/ H2 O+el 0,1%de HCOOH,del 30→65%,15 minutos) 466,11 467,4 1 H-RMN (300 MHz, DMSO-d6 ) 2,12 (s, 3H)2,22 (s, 3H) 2,24 (s, 3H) 3,04 (s, 3H) 6,73 (s,1H) 7,04 (s, 1H) 7,17 (s, 1H) 7,42 -7,65 (m,5H) 7,91 (d, J=9,08 Hz, 1H) 8,16 (d, J=1,98Hz, 1H) 10,58 (s, 1H)
26
imagen46 2(f) C (CH3 CN/ H2 O+el 0,1%de HCOOH,del 30→65%,15 minutos) 468,09 469,4 1 H-RMN (300 MHz, DMSO-d6 ) 2,18 (s, 3H)3,04 (s, 3H) 3,80 (s, 3H) 6,75 (s, 1H) 6,81 (dd,J=8,26, 2,48 Hz, 1H) 6,87 (d, J=2,64 Hz, 1H)7,32 (d, J=8,42 Hz, 1H) 7,41 -7,66 (m, 5H)7,91 (d, J=8,92 Hz, 1H) 8,16 (d, J=1,82 Hz,1H) 10,58 (s, 1H)
27
imagen47 2(g) B (Hex/ EtOAc= 8/2) 390,15 391,6 1 H-RMN (300 MHz, DMSO-d6 ) 0,93 (t, J=7,10Hz, 3H) 2,32 (s, 3H) 2,69 -2,89 (m, 2H) 3,13 3,40 (m, 2H) 4,61 (dd, J=10,24, 9,25 Hz, 1H)6,48 (d, J=8,26 Hz, 1H) 7,05 -7,61 (m, 10 H)10,11 (s, 1H)
28
imagen48 2(h) A (EtOH/H2 O= 2:8) 432,12 433,5 1 H-RMN (300 MHz, DMSO-d6 ) 1,79 (qd,J=7,20, 7,06 Hz, 2H) 2,04 (t, J=7,20 Hz, 2H)4,22 (t, J=7,27 Hz, 2H) 6,54 (s, 1H) 7,34 7,69 (m, 11H) 8,06 (d, J=1,61 Hz, 1H) 10,33(s, 1H) 12,28 (s. a., 1H)
29
imagen49 2(h) A (EtOH/H2 O= 2:8) 418,11 419,8 1 H-RMN (300 MHz, DMSO-d6 ) 2,54 (t, J=7,90Hz, 2H) 4,42 (t, J=7,90 Hz, 2H) 6,54 (s, 1H)7,37 -7,64 (m, 11H) 8,04 (d, J=1,83 Hz, 1H)10,33 (s, 1H) 12,31 (s. a., 1H)
30
imagen50 2(h) A (EtOH/H2 O= 2:8) 404,09 405,6 1 H-RMN (300 MHz, DMSO-d6 ) 4,89 (s, 2H)6,60 (s, 1H) 7,34 -7,65 (m, 11H) 8,05 (s, 1H)10,34 (s, 1H) 13,00 (s. a., 1H)
31
imagen51 2(a) A(EtOAc/EtOH=5:1) 417,12 418,2 1 H-RMN (300 MHz, DMSO-d6 ) 2,35 -2,46 (m,2H) 4,31 -4,44 (m, 2H) 6,54 (s, 1H) 6,84 (s.a., 1H) 7,33 (s. a., 1H) 7,37 -7,68 (m, 11H)8,04 (d, J=1,98 Hz, 1H) 10,32 (s, 1H)
32
imagen52 2(a) A (EtOAc) 445,16 446,3 1 H-RMN (300 MHz, DMSO-d6 ) 2,63 (t, J=7,60Hz, 2H) 2,72 (s, 3H); 2,73 (s, 3H); 4,40 (t,J=7,89 Hz, 2H); 6,54 (s, 1H); 7,35 -7,66 (m,11H); 8,05 (d, J=1,75 Hz, 1H); 10,33 (s, 1H).
33
imagen53 2(a) A (Es/AcOEt) 402,92 403,3 1 H-RMN (300 MHz, DMSO-d6 ) δ 10,22 (s,1H), 7,90 (s, 1H), 7,53 -7,61 (m, 2H), 7,40 7,53 (m, 2H), 7,26 -7,39 (m, 6H), 7,15 -7,26(m, 1H), 6,26 (s, 1H), 4,14 (q, J = 7,02 Hz,2H), 3,04 (s, 4H), 1,22 (t, J = 7,02 Hz, 3H)
34
imagen54 2(a) A (iPrOH /AcOEt / Pr2 O) 388,89 389,0 1 H-RMN (DMSO-d6 ): 10,23 (s, 1H); 7,89 (s,1H); 7,49 (m, 4H); 7,26 (m, 7H); 6,17 (s, 1H);4,15 (s, 2H); 4,09 (q, J = 6,9 Hz, 2H); 1,04 (t,J= 7,1 Hz, 3H).
35
imagen55 2(i) B (Es/AcOEt;del 90→66%de Es) 482,45 482,3 1 H-RMN (DMSO-d6 ): 10,41 (s a, 1H); 10,21 (sa, 1H); 8,09 (s, 1H); 7,85 (d, J= 8,5 Hz, 1H);7,82 (m, 3H); 7,71 (m, 2H); 7,59 (d, J= 8,5 Hz,1H); 7,49 (d, J= 8,5 Hz, 1H); 7,25 (t, J= 8,5Hz, 2H); 7,31 (s, 1H); 7,11 (t, J= 8,5 Hz, 1H);4,61 (t, J= 7,5 Hz, 2H); 4,47 (t, J= 5,0 Hz, 1H);3,41 (d, J= 7,5 Hz, 2H); 1,91 (m, 2H).
36
imagen56 2(a) B (Es/AcOEt;del 90→60%de Es) 443,30 443,2 1 H-RMN (300 MHz, DMSO-d6 ) δ 10,53 (s,1H), 8,00 (d, J = 1,98 Hz, 1H), 7,63 -7,73 (m,2H), 7,45 -7,61 (m, 4H), 7,27 -7,41 (m, 3H),6,53 (s, 1H), 4,89 (t, J = 5,28 Hz, 1H), 4,20 (t,J = 6,28 Hz, 2H), 3,63 (q, J = 6,17 Hz, 2H)
37
imagen57 2(a) B (Es/AcOEt;del 90→60%de Es) 476,85 477,2 1 H-RMN (300 MHz, DMSO-d6 ) δ 10,39 (s,1H), 7,98 (d, J = 1,98 Hz, 1H), 7,73 -7,84 (m,2H), 7,54 -7,71 (m, 5H), 7,51 (d, J = 8,92 Hz,1H), 7,36 (dd, J = 2,15, 8,75 Hz, 1H), 6,56 (s,1H), 4,88 (t, J = 6,11 Hz, 1H), 4,21 (t, J = 6,11Hz, 2H), 3,63 (q, J = 6,06 Hz, 2H)
38
imagen58 2(a) B (Es/AcOEt;del 90→60%de Es) 460,40 461,4 1 H-RMN (300 MHz, DMSO-d6 ) δ 10,60 (s,1H), 7,97 (d, J = 1,98 Hz, 1H), 7,60 -7,81 (m,5H), 7,51 (d, J = 8,92 Hz, 1H), 7,26 -7,41 (m,3H), 6,53 (s, 1H), 4,89 (t, J = 5,45 Hz, 1H),4,20 (t, J = 6,11 Hz, 2H), 3,63 (q, J = 6,17 Hz,2H)
imagen59
imagen60

Claims (3)

  1. E11194457
    03-11-2014
    REIVINDICACIONES
    1.
    Compuesto intermedio de fórmula (III):
    5
    imagen1
    en la que
    10 G1, G2 y G3, que pueden ser idénticos o diferentes, son un átomo de nitrógeno o un grupo CH;
    R1 es un grupo alquilo (C1-C6), cicloalquilo (C3-C7), alquil (C1-C6)-ORI, (CH2)nCONRIIRIII , (CH2)nCORI, (CH2)nCOORII, (CH2)nOCORI, SO2RI, (CH2)nNRIISO2RI, (CH2)nSO2RI, opcionalmente sustituido con 1 a 3 grupos
    15 hidroxilo, en los que n es un entero de 1 a 6, RI es un grupo alquilo (C1-C3) o alquil (C1-C3)-OH, y RII y RIII , que pueden ser idénticos o diferentes, son un átomo de hidrógeno o un grupo alquilo (C1-C3);
    W es un enlace σ, o un grupo alquilo (C1-C6), alquenilo (C2-C6), O-alquilo (C1-C6), O-alquenilo (C2-C6), (CH2)pCO(CH2)q o (CH2)pC(OH)(CH2)q, en los que p y q, que pueden ser idénticos o diferentes, son un entero de 0
    20 a3;y
    R2 es un grupo fenilo o piridina, opcionalmente sustituido con de 1 a 3 sustituyentes, que pueden ser idénticos o diferentes, representados por un grupo L-M, en el que L es un enlace σ, o un grupo alquilo (C1-C6), alquenilo (C2-C6), alquinilo (C2-C6), O-alquilo (C1-C6), O-alquenilo (C2-C6), O-alquinilo (C2-C6), y M es un átomo de hidrógeno o
    25 de halógeno, o un grupo OH, CF3, NO2, COORII, SO2NHRII, CH2CONRIIRIII, NRIIRIII, SO2RIV, NHSO2RIV, PORIVRV u OPORIVRV, en los que RII y RIII, que pueden ser idénticos o diferentes, presentan el significado anterior, y RIV y RV, que pueden ser idénticos o diferentes, son un grupo alquilo (C1-C3),
    siempre que
    30 cuando G1, G2 y G3 son todos un grupo CH, R1 es un grupo alquilo (C1-C6) o cicloalquilo (C3-C7), opcionalmente sustituido con 1 a 3 grupos hidroxilo, W es un enlace σ, y el enlace entre los átomos de carbono en la posición 2 y 3 es un doble enlace,
    35 R2 no sea un grupo fenilo o piridina, opcionalmente sustituido con 1 a 3 sustituyentes, que pueden ser idénticos o diferentes, seleccionados de entre halógeno, alquilo (C1-C6) opcionalmente sustituido con un grupo hidroxilo, trifluorometilo, nitro, amino, di(alquil (C1-C3))amino, hidroxilo, alcoxilo (C1-C3), COOH, COORII , SO2CH3, SO2NHCH3, NHSO2CH3, PORIVRV, OPORIVRV, alquil (C1-C6)-COOH y alquenil (C2-C6)-COOH;
    40 y siempre que
    cuando G1 es N, y G2 y G3 son un grupo CH, R2 no sea un grupo aromático divalente sustituido con un grupo L-M representado por un grupo O-alquilo (C1-C6), O-alquenilo (C2-C6) y O-alquinilo (C2-C6).
    45
  2. 2. Compuesto intermedio según la reivindicación 1, caracterizado por que dicho R1 se selecciona de entre grupo alquilo (C1-C3), alquil (C1-C3)-ORI, (CH2)nNRIIRIII , (CH2)nCONRIIRIII , (CH2)nCORI, (CH2)nCOORII , (CH2)nOCORI, SO2RI, (CH2)nNRIISO2RI, (CH2)nSO2RI, opcionalmente sustituido con 1 a 3 grupos hidroxilo, en los que n es un entero de 1 a 4, RI es un grupo alquilo (C1-C3) o alquil (C1-C3)-OH, y RII y RIII, que pueden ser idénticos o diferentes, son un
    50 átomo de hidrógeno o un alquilo (C1-C3).
  3. 3. Compuesto intermedio según la reivindicación 1, caracterizado por que dicho R1 se selecciona de entre grupo alquilo (C1-C3), alquil (C1-C3)-ORI, (CH2)nCONRIIRIII , (CH2)nCORI, (CH2)nCOORII , (CH2)nOCORI, SO2RI, (CH2)nNRIISO2RI, (CH2)nSO2RI, opcionalmente sustituido con 1 a 3 grupos hidroxilo, en los que n es un entero de 1 a
    55 3, RI es un grupo CH3, C2H5, CH2OH, C2H4OH, y RII y RIII, que pueden ser idénticos o diferentes, son un átomo de hidrógeno o un grupo CH3, C2H5.
    31
    imagen2
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