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BY (11) 10373
(13) C1
(46) 2008.02.28
(19)
(12)
(51)
,
(54)
(21)
: a 20040538
(22) 2002.11.08
(31) P200102517 (32) 2001.11.14 (33) ES
(85) 2004.06.14
(86) PCT/ES02/00518, 2002.11.08
(87) WO 03/042175, 2003.05.22
(43) 2004.12.30
(71)
:
.
,
. (ES)
(72)
:
,
,
,
;
(ES)
;
-
(73)
:
.
,
. (ES)
(56) EP 0747353 A2, 1996.
FR 1601070, 1970.
EP 0733628 A1, 1996.
WO 98/46570 A1.
SU 1498386 A3, 1989.
(57)
1.
I:
R3
A
BY 10373 C1 2008.02.28
(2006)
C 07D 209/00
C 07D 401/00
C 07D 409/00
C 07D 413/00
A 61K 31/403
A 61P 25/00
R2
(CH2)n
N
S
O
, (I)
O
N
R1
5-
1
1
2
2
6-
,
,
,
, C1-C4
5,
1
,
,
,
1
R
n
R2
,
C1-C4
0, 1, 2, 3
-NR4R5
2
,
1
,
1
;
, C1-C4
4;
3
2
;
:
6,
-
BY 10373 C1 2008.02.28
N
R1
N
R1
N
N
,
,
,
,
N
R1
N
O
N
,
,
N
N
N
,
N
N
,
N
1
,
R
,
N
1
R
;
3
R,R
4
R
5
C1-C4
,
.
2.
N-[3-(2,
N-[3-(2N-[3-(2,
N-[3-(2,
N-[3-(1,
N-[3-(1-
. 1,
,
]-5-
)-1
-5-
)-1
)-1
-5- ]-5-5- ]-5-
)-1
-5-
,
[b]
-3-
-2-
-2-
,
-3-
[b]
]-6-
-
-2-
[2,1-b]
-
-5-
-
-4-
)-1
-5-
]-5-
-3-
[b]
-2-
-
-4-
)-1
-5-
]-5-
-3-
[b]
-2-
-
-4-4-1-
)-1
)-1
-5-5-
]-5-
,
N-[3-(1N-[3-(1N-[3-(4-
-1
-2-
,
-8-5-
]-5-
,
-3-
[b]
-2-
,
N-[3-(2N-[3-(2N-[3-(2N-{3-[2-(
,
N-[3,
N-[3-(2,
N-[3-(2,
N-[3-(
,
N-[3-(2,
N-[3-(3,
N-{3-[2-(
N-{3-[2-(
-4-
)-1
)-1
)-1
]-1
-1
-5)-1
)-1
-7-
-5-
]-1
]-5-
-3-
-5-52
,
,
-2-2-
[b]
-3-
-2[b]
[2,1-b]
]-5}-5-
-3-
-
-2-
[b]
]-6-
-5-
-2-4,
[b]
[b]
-3-
-5- ]-5-5-
]-1
-3-
]-5-
)-1
)-1
-4-
]-5-
-5-
)-1
-1-
-5- ]-5-(2-5- ]-2,1,3-5-8-5- }-5-3-
-
-2-
-
-5[b]
-2-
-3-
[b]
-8-
.
-2-
-
BY 10373 C1 2008.02.28
3.
I
,
O
,
-
,
-
O
,
S
A
. 1,
II:
(II)
X
. 1;
,
,
5-
-
III:
R3
(CH2)n
R2
N
H
,
(III)
N
R1
n, R1, R2
R3
,
. 1,
.
4.
R4, n
I
. 1,
C1-C4
. 1, R3
,
,
R2, R4, n
C1-C4
5.
,
. 1,
.
R3
I
,
-4-
. 1, n = 0
R
,
,
R1,
I,
1
. 1, n = 0
,
R1.
6.
n = 0 R2
1
R1.
7.
. 1,
I
8.
5- 6
-
R
1
1
R1, R3
2
,
,
R1, R3
1,2,3,6-
. 1,
2
,
4-
R1, R2,
,
1
I,
R,
,
I
4-
. 1, n = 0 R2
R1 ,
I,
R1, R3
1,2,3,6-
R1, R3
, . 1,
. 1,
,
,
-4-
,
I
,
.
,
,
,
,
I
.1
2
-
,
-
.
9.
.1
,
,
,
(ADHD,
,
,
)
3
BY 10373 C1 2008.02.28
,
5-
,
6
.
10.
I:
R3
A
2
(CH2)n R
N
S
O
,
O
(I)
N
1
R
51
1
6-
2
2
6-
,
,
,
,
, C1-C4
5,
1
,
2
,
,
,
,
,
C1-C4
R1
n
R2
3
2
;
, C1-C4
0, 1, 2, 3
4;
-NR4R5
N
1
1
R1
N
;
:
R1
N
N
,
,
,
,
N
R1
N
O
N
,
,
N
N
,
,
N
N
N
R1
N
,
N
,
R1
;
3
R,R
4
R
5
C1-C4
,
,
,
,
,
,
(ADHD,
,
,
)
5-
,
6
I,
.
,
,
,
.
4
-
BY 10373 C1 2008.02.28
R3
A
(CH2)n
2
R
N
S
O
(I)
O
N
R
1
,
,
-
.
(5- )
7
(5-HT1-5- 7),
14
[D. Hoyer, et al., Neuropharmacology, 1997, 36,
419]. 5- 6
,
[F.J. Monsma, et al., Mol. Pharmacol., 1993, 43, 320; M. Ruat, et al., Biochem. Biophys. Res. Commun., 1993, 193, 268],
[R. Kohen, et al., J. Neurochem., 1996, 66, 47].
5- 6
,
.
5- 6
,
[ . Yoshioka, et al., Ann. NY Acad. Sd., 1998, 861, 244; A. Bourson, et al., Br. J.
Pharmacol., 1998, 125, 1562; D.C. Rogers, et al., Br. J. Pharmacol. Suppl., 1999, 127, 22P;
A. Bourson, et al., J. Pharmacol. Exp. Ther., 1995, 274, 173; A.J. Sleight, et al., Behav. Brain
Res., 1996, 73, 245; T.A. Branchek, et al., Annu. Rev. Pharmacol. Toxicol., 2000, 40, 319;
. Routledge, et al., Br. J. Pharmacol., 2000, 130, 1606].
,
5- 6
[B.L. Roth, et al., J. Pharmacol. Exp. Ther., 1994, 268,
1403; C.E. Glatt, et al., Mo1. Med., 1995, 1, 398; F.J. Mosma, et al., Mo1. Pharmacol., 1993, 43,
320; T. Shinkai, et al., Am. J. Med. Genet., 1999, 88, 120].
5- 6
(ADHD,
) [W.D. Hirst, et
al., Br. J. Pharmacol., 2000, 130, 1597; . Gerard, et al., Brain Research, 1997, 746, 207;
M.R. Pranzatelli, Drugs of Today, 1997, 33, 379].
WO 01/32646
5- 6
,
,
6.
0733628
,
,
5-HT1F
,
.
,
,
, ,
,
.
I,
,
.
5-
,
6
,
,
,
,
,
5
BY 10373 C1 2008.02.28
,
,
(ADHD,
)
,
,
5-HT6
.
,
,
R3
A
I:
2
R
(CH2)n
N
S
O
,
O
(I)
N
1
R
,
5-
:
,
6,
,
5-
2
6-
,
;
,
,
1
3
,
C1-C4
R1
n
R2
,
1
,
2
2
,
, C1-C4
1
1
,
1
2
;
0, 1, 2, 3
-NR4 R5
N
R1
N
, C1-C4
4;
;
:
N
N
R1
,
,
,
,
N
R
N
O
1
N
,
,
N
N
,
N
,
N
,
N
N
,
N
,
R1
R1
;
R3, R4
R5
1
,
4
.
1
,
,
,
-2-
-
-2-
-
4
1
4
,
,
,
,
,
.
,
,
2.
[1] N-[3-(2,
[6] N-[3-(2[7] N-[3-(2,
:
. 1,
:
)-1
-5-
)-1
)-1
-5- ]-5-5- ]-5-
6
]-5-
-3-
[b]
-2-
-3-
,
[b]
BY 10373 C1 2008.02.28
[9] N-[3-(2,
[10] N-[3-(1,
[11] N-[3-(1-
)-1
-5-
]-6-
[2,1-b]
-5-
-
-4-
)-1
-5-
]-5-
-3-
[b]
-2-
-4-
)-1
-5-
]-5-
-3-
[b]
-2-
-4-4-1-
)-1
)-1
-5-5-
]-5-
,
[14] N-[3-(1[16] N-[3-(1[19] N-[3-(4-2,
[20] N-[3-(2[21] N-[3-(2[22] N-[3-(2[27] N-{3-[2-(
,
[30] N-[3,
[32] N-[3-(2,
[33] N-[3-(2,
[38] N-[3-(
2,
[39] N-[3-(2,
[43] N-[3-(3,
[44] N-{3-[2-(
2,
[50] N-{3-[2-(
-1
)-1
)-1
)-1
]-1
-4-
-5-
-5-
)-1
]-5-
-5-
]-5-
)-1
)-1
-5-5-
)-1
,
,
-2-2-
-
-3-
[b]
-2-
-
-3-
[b]
-2-
-
]-5-
-3-
[b]
[2,1-b]
-5- ]-5-
-3-
-5-
}-5-
]-1
-
[b]
]-6-
]-1
-4-
[b]
-2-4,
[b]
-3-
-5- ]-5-
)-1
-1-
,
,
-5- ]-5-(2-5- ]-2,1,3-5-8-5- }-5-3-
-1
-7-
-2-8]-5-3-
-5-
-
-5-
[b]
-
-2-
-3-
-
[b]
-8-
-
.
-
I,
,
,
,
,
,
,
,
,
,
,
,
,
,
.
R1, R2, R3, R4, n
I,
,
,
-
.
.
II
-
:
O
O
,
S
A
(II)
X
,
I,
,
,
5-
(III)
X
,
-
:
7
BY 10373 C1 2008.02.28
R3
R2
(CH2)n
N
H
,
(III)
N
R1
n, R1, R2
R3
I,
,
.
II
,
III
,
-
,
,
,
-
,
,
,
,
,
,
.
,
,
,
0°
.
,
24
-
5
-
.
,
,
pH
,
-
,
,
;
,
,
,
-
.
II
,
III
,
[J.E. Macor, R. Post K. Ryan,
Synt Comm., 1993, 23, 1, 65-72; J. Guillaume, . Dumont, J. Laurent N. Nedelec, Eur. J. Med.
Chem., 1987, 22, 33-43; M.L. Saccarello, R. Stradi, Synthesis, 1979, 727].
.
I,
R1, R2, R4, n
,
,
3
R
,
1
4
I,
R1, R2, R4, n
R3
,
.
,
,
,
,
,
,
,
,
,
,
,
,
,
,
,
,
,
,
.
0°
,
1 24
.
[
. Gilbert, Synthesis, 1969, 1, 3].
8
BY 10373 C1 2008.02.28
,
pH
,
,
,
,
-
,
,
,
,
.
.
R1, R3
,
I,
2
, n=0
41
3
R,R
I,
R
-
,
,
1,2,3,6-
, n=0
R2
-4- .
,
-
,
25
,
,
150 ° .
,
-
,
.
,
.
1
48
.
,
100 ° ,
,
50
1
pH
48
.
-
,
,
;
,
,
,
-
.
I,
R1, R3
,
,
I,
R1, R3
,
R2
5-
,n=0
.
D.
R2
4I,
,
2
, n=0
R
1,2,3,6-
-4-
,
,n=0
,
R1, R3
-
.
,
,
,
,
,
-
,
,
1
,
,
10
,
,
1
3
2
5
-
.
.
-
.
,
.
.
I
,
9
,
BY 10373 C1 2008.02.28
,
,
,
,
,
,
,
,
,
,
,
-
,
,
,
,
,
,
.
.
,
[Protective groups in Organic Chemistry, ed J. F.W. McOmie, Plenum Press,
1973; T.W. Greene & P.G.M. Wuts, Protective Groups in Organic Chemistry, John Wiley &
sons, 1991].
.
,
,
, I
.
I
,
5- 6
,
,
,
,
,
,
,
,
,
(ADHD,
/
)
,
5- 6
,
.
.
5-
,
6
,
.
,
,
.
7.
N-[3-(2-
)-1
-5-
]-5-
-3-
[b]
-
-23,05
5-
-3-
(15
[b]
) 5-
-3-(2-
-2-
20
20
)-1H4,21
.
.
100
(15
)
,
,
.
.
-
,
5,5 (82 %) N-[3-(2[b]
-2= 226-227 ° .
.
26.
N-[3-(2)-1
285
(0,7
) N-[3-(2(
17) 80
(0,7
)
)-1
-5- ]-N)-1
10
-5-
]-5-
-3-
-
-2-53
-2-
-
BY 10373 C1 2008.02.28
30
.
105
3
(0,7
)
.
.
,
,
N-[3-(2-
)-1
-5-
]-N= 49-50 ° .
-2-
-
.
18.
N-[3-(1-
-1,2,3,6-
-4-
)-1
-5-
-
1712
) N-[1
(2,64
1-
(13,2
)
100
-5-
-1-
850
,
596
(5,28
48
-4,
1,2,3,6-
-5.
-4D.
12.
N-[3-(1417
-1-
3
-5-1,2,3,6-
-1-45%
100
)-1 -
,
(65 %) N-[3-(1-
-4-
-1-
N-[3-(21,05 (2,5
2)
.
.
(52 %) N-[3-(1-
.
,
272
,
573
-1-
-5= 244-245 ° .
-4- )-1
) N-[3-(150
(1
20
-5= 254-256 ° .
.
3.
,
)-1H-
)
.
-
) N-[3-(210
)-1H)-1H0,6
N-[3-(2-
1-
-54,2 N
)-1
-5-
-1-
-1-5= 255-257 ° .
.
11
)-1 -
-
R3
A
(CH2)n
R2
N
S
O
O
N
R1
.
. R1
R2
n
R3
A
.,
-1
1
(300
), δ (
)
°C
(CH3CH2)2N-
2
H
Cl
-
S
2
12
3
(CH3CH2)2N-
2
H
-
(CH3CH2)2N-
2
H
HCl
Cl
4
(CH3CH2)2N-
2
H
-
Cl
3387, 2970,
2931, 1466,
1236, 1158,
170-173
1107, 1080,
993, 862, 805,
657, 565
3451, 3337,
2972, 1466,
1319, 1237,
170
1157, 1132,
1091, 991, 770,
675, 583, 481
0.88 ( , 6 , J = 7.1 ); 2.28 ( , 3H); 2.30-2.46 ( , 6 );
2.58 ( , 2 ); 6.85 ( , 1 , J = 8.6, 2.0 ); 7.10 ( , 2 );
7.20 ( , 1H, J = 8.6 ); 7.50 ( , 1 , J = 8.7, 2.0 );
7.90 ( , 1 , J = 2.0 ); 7.98 ( , 1 , J = 8.7 );
10.10 ( , 1H); 10.80 ( , 1 ). (
-d6)
0.90 ( , 6 , J = 7.1 ); 2.33-2,55 ( , 8 );6.69 ( , 1 ,
J = 8.7, 1.8 ); 6.95 ( , 1 ); 7.02 ( , 1H, J = 1,8 );
7.05 ( , 1H, J = 8.7 ); 7.47 ( , 1 , J = 7.7 ); 7.63
, 1 ); 7.70 ( , 1H); 8.01 ( , 2 ); 8.12 ( , 1 ,
J = 7.5 ); 8.77 ( , 1 , J = 8.1 ); 10.10 ( , 1H);
10,66 ( , 1H). (
-d6)
1.22 ( , 6 , J = 7.2 ); 2.91-3.18 ( , 8 ); 6.65 ( , 1H,
3378, 3065,
J = 8.6 ); 7.08 ( , 1H, J = 8.6 ); 7.17 ( , 1H);
2558, 2489,
7.20 ( , 1H, J = 1.8 ); 7.54 ( , 1 , J = 7.8 );
1460, 1317,
255-257
7.63 ( , 1 ); 7.70 ( , 1 ); 8.03 ( , 1 , J = 7.8 );
1162, 1143,
8.08 ( , 1 , J = 7.1 ); 8.14 ( , 1 , J = 8.2 );
1131, 811, 687,
8.79 ( , 1 , J = 8.4 ); 10.26 ( , 1 ); 10.90 ( , 1 );
602, 588
11.01 ( , 1H). (
-d6)
3309, 3047,
2974, 1566, 0.95 ( , 6 , J = 7.1 ); 2.44-2.58 ( , 6 ); 2.66 ( , 2 );
1467, 1235, 6.79 ( , 1H, J = 8.6, 1.7 ); 7.08 ( , 1 , J = 0.9 );
168-170
1167, 1143, 7.13 ( , 1 , J = 1.7 ); 7.23 ( , 1H, J = 8.6 );
1116, 1001, 7.58 ( , 2 ); 7.87 ( , 1 ); 9,95 ( , 1 ); 10.82 ( , 1H).
-d6)
910, 799, 672,
587
BY 10373 C1 2008.02.28
1
CH3
.
. R1
R2
n
R3
A
.,
-1
1
(300
), δ (
)
°C
5
H
(CH3CH2)2N-
(CH3CH2)2N-
2
2
H
H
Cl
2
H
-
3375, 2978,
1467, 1417,
180-181
1236, 1212,
1115, 994, 624
-
226-227
3422, 3238,
1332, 1155,
1114, 1079,
986, 861, 803,
655, 564
203-205
3357, 1475,
1282, 1157,
112, 990, 957,
809, 773, 613,
587, 557, 498
S
7
(CH3)2N-
-
CH3
Cl
13
S
8
(CH3)2N-
2
H
-
S
9
H
(CH3)2N-
2
N
H
-
N
215
.)
Cl
10
H3C N
0
H
Cl
CH3
-
S
250
.)
3247, 3094,
1467, 1272,
1261, 1230,
625
2.17 ( , 6 ); 2.36 ( , 2 ); 2.65 ( , 2 ); 6.77 ( ,
J = 8.6, 1.7 , 1 ); 7.07 ( , 1 ); 7.09 ( , 1 );
7.18 ( , J = 8.6 , 1 ); 7.51 ( , J = 4.5 , 1H);
7.81 ( , J = 4.5 , 1 ); 10.80 ( , 1 ). (
-d6)
1.53-1.80 ( , 4 ); 2.26 ( , 3H); 2.39-2.71 ( , 6 ); 3.02
3407, 2390,
, 2 , J = 8.8 ); 6.76 ( , 1 , J = 8.8 ); 7.05 ( , 1H);
1466, 1334,
7.11 ( , 1 );7.19 ( , 1H, J = 8.8 ); 7.51 ( , 1H,
1156, 113,
J = 8.7 ); 7.91 ( , 1H); 8.00 ( , 1 , J = 8.7 );
1080, 651, 565
10.10 ( , 1 ); 10.90 ( , 1H). (
-d6)
BY 10373 C1 2008.02.28
6
H
3387, 2971,
1323, 1157,
161-163
1095, 765, 670,
590
0.89 ( , 6 , J = 7.1 ); 2.32-2.55 ( , 6 ); 2.62 ( , 2 );
6.85 ( , 1H, J = 8.6 ); 7.08 ( , 1H, J = 2.0 );
7.13 ( , 1H); 7.18 ( , 1H, J = 8.6 ); 7.33-7.50 ( , 3 );
7.64 ( , 2 , J = 7.5 ); 7.72 (
, 2 , J = 8.6 );
7,78 (
, 2 , J = 8.6 ); 9.80 ( , 1 );
10.75 ( , 1 ). (
-d6)
0.96 ( , 6 , J = 7.1 ); 2.52 ( , 4 ); 2.57 ( , 2 );
2.66 ( , 2 ); 6.83 ( , 1H, J = 8.6, 1.9 ); 7.11 ( , 1 ,
J = 4.0 ); 7.14 ( , 1H, J = 1.9 ); 7.17 ( , 1H,
J = 1.9 ); 7.20-7.24 ( , 2 ); 10.01 ( , 1 );
10.81 ( , 1 ). (
-d6)
2.04 ( , 6 ); 2.23 ( , 2 ); 2.28 ( , 3H); 2.59 ( , 2 );
6.83 ( , 1H, J = 8.4, 1.5 ); 7,09 ( , 2 ); 7.19 ( , 1H,
J = 8.4 ); 7.49 ( , 1 , J = 8.7, 1.6 ); 7.91 ( , 1 ,
J = 1.6 ); 7.99 ( , 1 , J = 8.7 ); 10,13 ( , 1 ),
10,79 ( , 1 ). (
-d6)
2.09 ( , 6 ); 2.21 ( , 2 ); 2.54 ( , 2 ); 6.69 ( , 1H,
J = 8.6, 1.7 ); 6,94 ( , 1H); 7.03 ( , 1 ); 7.06 ( , 1 ,
J = 8.1 ); 7.49 ( , 1H, J = 7.8 ); 7.64 ( , 1H);
7.71 ( , 1H); 8.02 ( , 2 ); 8.13 ( , 1H, J = 8.1 );
8.79 ( , 1 , J = 8.4 ); 10.10 ( , 1H); 10.68 ( , 1 ).
-d6)
.
. R1
R2
n
R3
A
.,
-1
1
(300
), δ (
)
°C
11
H
H3C N
0
H
CH3
Cl
HCl
12
H
0
13
H3C N
0
14
H3C N
0
H3C N
0
15
H
H
HCl
Cl
H
1.49 ( , 2 ); 1.61 ( , 2 ); 2.14 ( , 2 ); 2.30 ( , 3H);
2.40 ( , 1 ); 2,90 ( , 2 , J = 10.6 ); 6.65 ( , 1H,
J = 8.6 ); 6.90 ( , 1H); 6.96 ( , 1H); 7.05 ( , 1 ,
J = 8.6 ); 7.46 ( , 1H, J = 7.51, 1.83 ); 7.64 ( ,
); 7.71 ( , 1H); 7.99 ( , 1H, J = 8.6 ); 8.03 ( , 1 ,
J = 8.6 ); 8.12 ( , 1 , J = 8.2 ); 8.77 ( , 1H,
J = 8.6 ); 10.07 ( , 1H); 10.71 ( , 1 ). (
-d6)
1.80 ( , 4 ); 2.74 ( , 4 ); 3.04 ( , 2 ); 3.39 ( , 2 );
3423, 3269,
6.63 ( , 1H, J = 8.6 ); 7.00 ( , 2 ); 7.08 ( , 1H,
3114, 2955,
212
J = 8.6 );7.49 ( , 1H, J = 7.7 ); 7.60-7.77 ( , 2 );
2733, 1469,
.)
8.04 ( , 2 , J = 7.5 ); 8.13 ( , 1 , J = 8.2 );
1321, 1155,
8.79 ( , 1 , J = 8.2 ); 10.16 ( , 1H); 10.66 ( , 1H);
1133, 947, 769
10.88 ( , 1 ). (
-d6)
1.62 ( , 2 ); 1.78 ( , 2 , J = 11.7 ); 1.99 ( , 2 );
3371, 2943,
2.18 ( , 3H); 2.55 ( , 1 ); 2.84 ( , 2 , J = 10.6 );
1468, 1410,
284
6.81 ( , 1 , J = 8.6 ); 7.07 ( , 1 ); 7.1 3 ( , 1 );
.)
1324, 1148,
7.16 ( , 1 ); 7.20-7.26 ( , 1H); 9.90 ( , 1 );
993, 604
10.83 ( , 1 ). (
-d6)
1.52 ( , 2 ); 1.67 ( , 2 ); 1.85 ( , 2 ) 2.08 ( , 3H);
3361, 2936, 2.44 ( , 1H); 2.67 ( , 2 , 10.25 ); 6.83 ( , 1H,
1318, 1155, J = 8.4 ); 7.01 ( , 1 ); 7,03 ( , 1 ); 7.19 ( , 1H,
247-248
1095, 767 670, J = 8.4 ); 7.35-7.50 ( , 3H); 7.63-7.73 ( , 4 );
587
7.79 (
, 2 , J = 7.6 ); 9.71 ( , 1H);
10.76 ( , 1H). (
-d6)
3343, 2938,
2929, 1470
254-256
1154, 1121,
1108, 988, 947,
805, 769, 589
14
H3C N
.)
-
S
-
1.75-1.92 ( , 4 ); 2.31 ( , 3H); 2.66 ( , 3H); 2.80 ( ,
1H); 2.95 ( , 2 ); 3.24 ( , 2 , J = 11.4 ); 6.76 ( , 1H,
J = 8.7 ); 7.07 ( , 1 ); 7.19 ( , 2 ); 7.50 ( , 1H,
J = 8.6 ); 7.93 ( , 1 ); 8.01 ( , 1H, J = 8.6 );
8,34 ( , 1 ); 10.90 ( , 1H); 11.01 ( , 1H). (
-d6)
BY 10373 C1 2008.02.28
S
220
3423, 3214,
3043, 2942,
2688, 1464,
1317, 1149,
1114, 1080,
748, 670, 646
.
. R1
R2
n
R3
A
.,
-1
1
(300
), δ (
)
°C
16
H
(CH3CH2)2N-
-
N
2
-
18
15
H
19
0
H3C N
H3C N
N
1
H
-
CH3
Cl
-
S
20
(CH3)2N-
2
N
S
-
BY 10373 C1 2008.02.28
17
0
H3C N
1.25-1.52 ( , 4 ); 1.85 ( , 2 ); 2.18 ( , 3 );
2.27 ( , 1 ); 2.74 ( , J = 11.4 , 2 ); 6.72 ( , J = 8.6,
2.0 , 1 ); 6.83 ( , J = 1.5 , 1 ); 6.90 ( , J = 2.0 ,
3398, 3257,
280
1H); 7.02 ( , J = 8.6 , 1 ); 7.57 ( , 1 ); 7.74 ( ,
2933, 1161,
.)
J = 8.4, 4.3 , 1 ); 8.12 ( , J = 7.3, 1.3 , 1H);
1143, 789, 589
8.19 ( , J = 8.2, 1.3 , 1 ); 8.52 ( , J = 8.4, 1.7 ,
); 9.21 ( , J = 4.3, 1.7 , 1 ); 9.36 ( , 1H);
10.64 ( , 1 ). (
-d6)
3199, 2970,
0.87 ( , J = 7.1 , 6 ); 2.39 ( , 6 ); 2.55 ( , 2 );
2930, 2870,
6.82 ( , J = 8.6 , 1 ); 7.05 ( , 1 ); 7.09 ( , 1 );
1327, 1153,
172-173
7.13 ( , J = 8.6 , 1 ); 7.60 ( , 2 ); 7.73 ( ,
1130, 1110,
J = 8.6 , 1H); 7.95 ( , J = 7.9 , 1H); 8.01 ( , 2 );
1075, 956, 676,
8.26 ( , 1H); 9.86 ( , 1 ); 10.71 ( , 1 ). (
-d6)
658, 551, 476
2.25 ( , 3 ); 2.31 ( , 2 ); 2.46 ( , 2 ); 2.90 ( , 2 );
3346, 2943, 5.34 ( , 1 ); 6.78 ( , J = 8.6, 2.0 , 1H);
1474, 1283, 7.09 ( , J = 1.5 , 1H); 7.14 ( , J = 8.6 , 1 );
244-245
1261, 1156, 7.25 ( , J = 2.0 , 1H); 7.49 ( , J = 7.8 , 1H);
.)
1123, 801, 771, 7.66 ( , 1 ); 7.75 ( , 1H); 8.04 ( , 2 );
589, 503
8.14 ( , J = 8.2 , 1H); 8.83 ( , J = 8.6 , 1 );
10.14 ( , 1 ); 11.03( , 1H). (
-d6)
2796, 1452, 1.80-2.26 ( , 8 ); 2.04 ( , 3 ); 2.30 ( , 3 ); 3.41 ( ,
1316, 1149,
); 6.89 ( , J = 8.6, 1.56 , 1H); 7.16 ( , 1H);
230
1114, 1080, 7.22 ( , J = 8.6 , 1H); 7.29 ( , 1H); 7.49 ( , J = 8.7,
.)
1001, 810, 646, 1.7 , 1 ); 7.90 ( , J = 1.7 , 1 ); 7.98 ( , J = 8.7 ,
559
); 10.13 ( , 1H); 10.93 ( , 1 ). (
-d6)
2.05 ( , 6 ); 2.32 ( , 2 ); 2.65 ( , 2 ); 6.86 ( ,
J = 8.6, 1.8 , 1 ); 7.10 ( , J = 1.8 , 1 ); 7.18 ( ,
3377, 2951,
J = 1.8 , 1H); 7.21 ( , J = 8.6 , 1H); 7.32 ( ,
2798, 1469,
209-211
J = 7.5, 4.6 , 1 ); 7.36 ( , J = 3.9 , 1H); 7.71 ( ,
1429, 1321,
J = 3.9 , 1 ); 7.83 ( , 1H); 7.93 ( , 1H); 8.49 ( ,
1158, 777, 594
J = 4.6 , 1 ); 9.97 ( , 1 ); 10.79 ( , 1 ).
-d6)
1
.
. R
1
R
2
n
R
3
A
.,
-1
(300
), δ (
)
°C
N
H
(CH3)2N-
2
H
22
H
(CH3)2N-
2
H
S
N
N
-
-
16
23
Cl
H
(CH3)2N-
2
H
-
24
H
(CH3)2N-
2
H
-
25
H
(CH3)2N-
2
H
-
O
BY 10373 C1 2008.02.28
21
2.10 ( , 6 ); 2.21 ( , 2 ); 2.56 ( , 2 );
3321, 2949,
6.72 ( , J = 8.6 , 1 ); 6.96 ( , 1H); 7.03 ( , 1H);
1474, 1327,
192
7.07 ( , J = 8.6 , 1H); 7.70 ( , 1 ); 8.07 ( , J = 7.0
1152, 1138,
, 1 ); 8.29 ( , J = 8.8 , 1 ); 10.14 ( , 1 );
1104, 981, 614
10.69 ( , 1 ). (
-d6)
2.07 ( , 6 ); 2.16 ( , 2 ); 2.51 ( , 2 ); 6.73 ( ,
3252, 2857,
J = 8.6, 1.8 , 1 ); 6.94 ( , 1 ); 6.99 ( , 1 ); 7.02 ( ,
1459, 1426,
250
J = 8.6 , 1H); 7.59 ( , J = 7.8 , 1 ); 7.73 ( ,
1333, 1161,
.)
J = 8.4, 4.1 , 1 ); 8.18 ( , 2 ); 8.50 ( , J = 8.4,
1144, 789, 680,
1.5 , 1 ); 9.20 ( , J = 4.1, 1.5 , 1 ); 9.45 ( ,
589
1H); 10.64 ( , 1 ). (
-d6)
3404, 2944, 2.01 ( , 6 ); 2.18 ( ,2 ); 2.57 ( ,2 ); 6.81 ( , J = 8.6,
2918,2855, 1.7 , 1H); 7.02 ( , 1 ); 7.05 ( , J = 1.7 , 1 );
230-240
1465, 1332, 7.15( , J = 8.6 , 1 ); 7.57 ( , 1 ); 7.82 ( , J = 7.5 ,
.)
1157, 1140, 1H); 7.91 ( , J = 8.9 , 1 ); 8.06 ( , J = 8.2 , 1 );
1080, 650, 639, 8.29 ( , J = 8.9 , 1H); 8.35 ( , 1 ); 9.94 ( , 1 );
526
10.74 ( , 1H). (
-d6)
3232, 2862,
2827, 2785,
2.16 ( , 6 ); 2.37 ( , 2 ); 2.66 ( , 2 );
1583, 1488,
6.80 ( , J = 8.6 , 1 ); 6.96-7.12 ( , 6 ); 7.14-7.25 ( ,
152-154
1333, 1248,
); 7.41 ( , 2 ); 7.64 ( , J = 8.5, 1.9 , 2 );
1155, 1091,
9.69 ( , 1 ); 10.75 ( , 1H). (
-d6)
755, 693, 571,
541
2.08 ( , 6 ); 2.32 ( , 2 ); 2.64 ( , 2 ); 6.83 ( ,
3451, 3388,
J = 8.6, 1.9 , 1H); 7.08 ( , J = 2.0 , 1 ); 7.11 ( ,
2950, 2775,
J = 1.9 , 1 ); 7.17 ( , J = 8.6 , 1H); 7.34-7.50 ( ,
184-186
1466, 1322,
); 7.66 ( , J = 7.5 , 2 ); 7.72 (
, J = 8.6 ,
1159, 1095,
); 7.79 (
, J = 8.6 , 2 ); 9.79 ( , 1 );
763, 670, 591
10.75 ( , 1H). (
-d6)
.
. R1
R2
n
R3
A
.,
-1
1
(300
), δ (
)
°C
26
H
O
N
2
2
Et
H
Cl
-
49-50
-
200-201
-
218-220
-
134-136
-
148-152
-
76-80
CH3
S
17
28
O
29
30
H
H
N
(CH3CH2)2N-
(CH3)2N-
2
H
2 CH3
Cl
1
CH3
S
31
(CH3CH2CH2)2N-
2
H
BY 10373 C1 2008.02.28
27
(CH3CH2)2N-
0.82 ( , J = 7.0 , 6 ); 0.98 ( , J = 7.0 , 3 ); 2.37
3386, 2970,
, J = 7.0 , 4 ); 2.49 ( , 2 ); 2.54 ( , 2 ); 3.66 ( ,
2931, 1474,
J = 7.1 , 2 ); 6.73 ( , J = 8.61, 1.6 , 1 ); 6.98 ( ,
1337, 1167,
1H); 7.17 ( , J = 1.6 , 1 ); 7.26 ( , J = 8.61 , 1H);
1151, 1130,
7.56-7.72 ( , 3H); 7.99-8.11 ( , 3H); 8.26 ( , 1 );
1073, 661, 550
10.97 ( , 1 ). (
-d6)
3366, 2951,
2.25 ( , 6 ); 2.27 ( , 3H); 2.62 ( , J = 7.9 , 2 ); 3.52
2816, 1460,
, 4 ); 6.84 ( , J = 8.2 , 1 ); 7.06 ( , 1 ); 7.10 ( ,
1421, 1319,
1H); 7.20 ( , J = 8.6 , 1H); 7.50 ( , J = 8.6 , 1H);
1283, 1157,
7.92 ( , 1H); 8.00 ( , J = 8.6 , 1H); 10.13 ( , 1 );
1114, 1078,
10.80 ( , 1H). (
-d6)
865, 651, 561
3389, 3152, 2.30 ( , 6 ); 2.56 ( , 2 ); 3.56 ( , 4 );
2916, 2819, 6.69 ( , J = 8.4 , 1H); 6.93 ( , 1H); 7.06 ( , 2 );
1466, 1313, 7.48 ( , J = 7.3 , 1 ); 7.67 ( , 2 ); 8.02 ( , 2 );
1157, 1129, 8.13 ( , J = 8.1 , 1 ); 8.78 ( , J = 8.1 , 1 );
1108, 771, 587 10.10 ( , 1H); 10.68 ( , 1 ). (
-d6)
0.98 ( , J = 7.1 , 6 ); 2.55 ( , 6 ); 2.70 ( , 2 );
2968, 2930,
3.67 ( , 3H); 6.84 ( . 1 ); 6.93 ( , J = 8.6, 2 , 1H);
1488, 1329,
7.10 ( , J = 8.7 , 1H); 7.18 ( , J = 1.7 , 1H); 7.26 ( ,
1159, 1131,
); 7.57 ( , 2 ); 7.67 ( , J = 8.7, 1.8 , 1 ); 7.84 ( ,
1074, 660, 550
3H); 8.27 ( , J = 1.7 , 1 ). (
-d6)
3398,2930,
1467, 1158, 1.89 ( , 6 ); 2.29 ( , 3H); 2.48 ( , 2 ); 6.83 ( , 1 );
1113, 1079, 7.18 ( , 3H); 7.50 ( , 1H); 7.91 ( , 1 ); 8.00 ( , 1 );
861, 803, 651, 10.13 ( , 1 ); 10.92 ( , 1 ). (
-d6)
561
0.82 ( , J = 6.7 , 6 ); 1.34 ( , J = 6,71 , 4 );
3399, 2959, 2.31 ( , 4 ); 2.40 ( , 2 ); 2.52 ( , 2 ); 6.69 ( ,
2931, 1466, J = 8.6 , 1H); 7.04 ( , 3H); 7.47 ( , 1H); 7.66 ( , 2 );
1159, 1132, 8.02 ( , 2 ); 8.11 ( , J = 8.1 , 1 ); 8.78 ( ,
802, 770, 588 J = 8.4 , 1H); 10.12 ( , 1H); 10.67 ( , 1H).
-d6)
.
. R1
R2
n
R3
A
.,
-1
1
(300
), δ (
)
°C
32
H
(CH3CH2CH2)2N-
2
H
CH3
Cl
-
S
H
(CH3CH2CH2CH2)2N
2
H
CH3
Cl
-
S
18
34
H
(CH3CH2CH2CH2)2N
2
H
-
Cl
35
(CH3CH2)2N-
36
37
(CH3CH2)2N-
H
H3C N
N
2
H
-
2
H
-
1
H
-
3404, 2972, 0.94 ( , J = 7.1 , 6 ); 2.50 ( , J = 7.1 , 4 );
1473, 1319, 2.59 ( , 2 ); 2.68 ( , 2 ); 6.94 ( , J = 8.6, 1.8 , 1 );
125-130
1142, 967, 745, 7.26 ( , 1 ); 7.59 ( , 2 ); 9.54 ( , 1 ); 10.77 ( , 1H).
541
-d6)
2.06 ( , 3H); 2.22 ( , 6 ); 3.36 ( , 2 ); 3.49 ( , 2 );
203
2809, 1340, 6.95 ( , J = 8.6, 1.8 , 1 ); 7.18 ( , 2 ); 7.24 ( , 2 );
.) 1150, 746, 542 7.37 ( , 3H); 7.45 ( , J = 1.8 , 1 ); 7.61 ( , 2 );
9.53 ( , 1 ); 10.90 ( , 1 ). (
-d6)
BY 10373 C1 2008.02.28
33
0.80 ( , J = 7.3 , 6 ); 1.31 ( , J = 7.3 , 4 );
3406, 2959,
2.26 ( , 7 ); 2.38 ( , 2 ); 2.56 ( , 2 ); 6.83 ( ,
2932, 2872,
J = 8.4, 1.8 , 1 ); 7.08 ( , 2 ); 7.20 ( , J = 8.6 ,
90-95
1466, 1157,
1H); 7.50 ( , J = 8.6, 2.0 , 1 ); 7.90 ( , J = 2.0 ,
1079, 861, 652,
); 7.99 ( , J = 8.6 , 1H); 10.12 ( , 1H);
561
10.79 ( , 1 ). (
-d6)
0.84 ( , J = 6.8 , 6 ); 1.24 ( , 8 ); 2.26 ( , 3H);
3398, 2956,
2.28 ( , 4 ); 2.39 ( , 2 ); 2.57 ( , 2 );
2930, 2870,
6.82 ( , J = 8.6, 1.9 , 1H); 7.09 ( , J = 1.8 , 2 );
79-80
1466, 1158,
7.18 ( , J = 8.6 , 1H); 7.50 ( , J = 8.6, 1.9 , 1 );
1080, 862, 801,
7.89 ( , J = 1.8 , 1 ); 7.98 ( , J = 8.6 , 1H);
653, 562
10.14 ( , 1H); 10.78 ( , 1H). (
-d6)
0.86 ( , J = 7.0 , 6 ); 1.29 ( , 8 ); 2.35 ( , 4 );
3291, 2955,
2.41 ( , 2 ); 2.53 ( , 2 ); 6.67 ( , J = 8.5, 1.9 , 1 );
2926, 2870,
7.09 ( , 3H); 7.48 ( , J = 7.9 , 1 ); 7.68 ( , 2 );
111-113
1327, 1158,
8.01 ( , 1 ); 8.04 ( , 1 ); 8.12 ( , J = 8.2 , 1 );
1136, 772, 676,
8.78 ( , J = 8.2 , 1 ); 10.13 ( , 1 ); 10.67 ( , 1 ).
611, 585
-d6)
3402, 2978, 0.88 ( , J = 6.7 , 6 ); 2.41 ( , 6 ); 2.49 ( , 2 );
1471, 1285, 6.71 ( , J = 8.1 , 1H); 6.88 ( , 1 ); 7.07 ( , 2 );
1162, 1135, 7.66 ( , 2 ); 7.84 ( , J = 7.0 , 1 ); 8.09 ( , J = 7.0
154-156
, 1H); 8.41 ( , J = 8.2 , 1 ); 8.79 ( , J = 8.6 ,
1018, 780, 629,
1H); 10.17 ( , 1 ); 10.71 ( , 1 ). (
-d6)
606
1
.
. R
1
R
2
n
R
3
A
.,
-1
(300
), δ (
)
°C
38
H
0
N
H
CH3
Cl
-
S
(CH3CH2)2N-
2
N
H
S
N
-
Cl
40
2
H
-
N
1
H
-
(CH3CH2)2N-
3
H
-
19
O
41
H
42
H
43
H3C N
N
(CH3CH2)2N-
3
Cl
CH3
-
S
BY 10373 C1 2008.02.28
39
1.12 ( , 3H); 1.81 ( , 9 ); 2.22 ( , 3H); 2.93 ( , 2 );
3413, 2929,
6.84 ( , J = 8.5, 1.7 , 1H); 6.99 ( , 1 ); 7.03 ( , 1H);
1157, 1113,
142-144
7,20 ( , J = 8.6 , 1H); 7.52 ( , J = 8.6, 2.0 , 1H);
1080, 862, 651,
7.90 ( , J = 1.7 , 1H); 8.00 ( , J = 8.6 , 1H);
564
10.01 ( , 1H); 10.61 ( , 1 ). (
-d6)
0.96 ( , J = 7.1 , 6 ); 2.53 ( , 6 ); 2.63 ( , 2 );
3338, 1466,
6.78 ( , J = 8.5, 1.6 , 1 ); 7.10 ( , 2 );
1270, 1237,
197-198
7.18 ( , J = 8.6 , 1 ); 7.51 ( , J = 4.6 , 1 );
117, 986, 626
7.80 ( , J = 4.6 , 1 ); 10.78 ( , 1 ). (
-d6)
3399, 3257,
2.27 ( , 6 ); 2.61 ( , J = 7.9 , 2 ); 3.52 ( , J = 4.6 ,
2920, 2855,
); 6.82 ( , J = 8.6, 2.0 , 1H); 7.06 ( , 1 ); 7.07 ( ,
2814, 1460,
); 7.15 ( , J = 8.6 , 1H); 7.61 ( , 2 ); 7.74 ( ,
85-90
1330, 1157,
J = 8.8, 1.8 , 1H); 7.96 ( , J = 8.1 , 1 ); 8.03 ( ,
1131, 1113,
); 8.27 ( , 1H); 9.87 ( , 1H); 10.74 ( , 1 ).
1074, 659, 551,
-d6)
477
3398, 2934,
2806, 1458, 2.11 ( , 3H); 2.32 ( , 6 ); 3.35 ( , 2 ); 3.56 ( , 2 );
99 -102
1331, 1284, 4.29 ( , 2 ); 6.98 ( , J = 8.2 , 1H); 7.29 ( , 7 );
1153, 1127, 7.53 ( , 1H); 9.40 ( , 1H); 10.94 ( , 1 ). (
-d6)
700, 542
0.86 ( , J = 7.0 , 6 ); 1.51 ( , J = 6.9 , 2 );
3259, 2973,
2.27 ( , J = 6.9 , 2 ); 2.35 ( , J = 7.0 , 4 );
2939, 2827,
2.46 ( , 2 ); 6.77 ( , J = 8.6 , 1 ); 7.00 ( , 1 );
128-130
1468, 1332,
7.10 ( , 2 ); 7.60 ( , 2 ); 7.72 ( , J = 8.8 , 1H);
1159, 1131,
7.95 ( , J = 7.9 , 1 ); 8.02 ( , 2 ); 8.26 ( , 1H);
1075, 670, 555
9.86 ( , 1 ); 10.67 ( , 1H). (
-d6)
0.88 ( , J = 7.0 , 6 ); 1.52 ( , 2 ); 2.29 ( , 5 );
3247, 2969,
2,37 ( , J = 7.0 , 4 ); 2.47 ( ,2 ); 6.81 ( , J = 8.6,
2938, 1467,
1.5 , 1 ); 7.06 ( , J = 1.6 , 1 ); 7.12 ( , J = 1.5 ,
156-158
1340, 1159,
1H); 7.18 ( , J = 8.6 , 1 ); 7.51 ( , J = 8.6, 2.0 ,
1113, 1080,
);); 7.91 ( , J = 2.0 , 1 ); 7.99 ( , J = 8.6 , 1H);
862, 666, 558
10.06 ( , 1H); 10.76 ( , 1H). (
-d6)
.
. R1
R2
n
R3
A
.,
-1
1
(300
), δ (
)
°C
N
44
2
H
CH3
Cl
-
S
H
N
2
H
-
46
20
H
47
N
(CH3CH2CH2)2N-
2
2
H
-
H
-
Cl
48
49
H
(CH3)2N-
2
H
-
(CH3)2N-
2
H
-
1.62 ( , 4 ); 2.29 ( , 3H); 2.30 ( , 4 ); 2.36 ( , 2 );
2.63 ( , 2 ); 6.86 ( , J = 8.6 , 1 ); 7.05 ( , 1H);
7.09 ( , 1 ); 7.21 ( , J = 8.6, 2.2 , 1 ); 7.50 ( ,
J = 8.7, 2.0 , 1H); 7.92 ( , 1H); 7.99 ( , J = 8.7,
2.2 , 1 ); 10,10 ( , 1H); 10.81 ( , 1 ). (
-d6)
1.66 ( , 4 ); 2.36 ( , 6 ); 2.58 ( , 2 ); 6.71 ( , J = 8.6 ,
); 6.93 ( , 1H); 7.02 ( , 1 ); 7.07 ( , J = 8.6 , 1H);
7.48 ( , 1H); 7,68 ( , 2 ); 8.02 ( , J = 7.2, 1.2 , 2 );
8.12 ( , J = 8.2 , 1H); 8.79 ( , J = 8.6 , 1 ); 10.10
, 1 ); 10.68 ( , 1 ). (
-d6)
1.60 ( , 4 ); 2.26 ( , 4 ); 2.35 ( , 2 ); 2.61 ( , 2 );
6.82 ( , J = 8.6, 2.0 , 1H); 7.05 ( , 2 ); 7.14 ( ,
J = 8.6 , 1H); 7.61 ( , 2 ); 7.74 ( , J = 8.6, 1.8 ,
); 7.95( , J = 7.9 , 1H); 8.02 ( , 2 ); 8.27 ( , 1 );
9.86 ( , 1H); 10.72 ( , 1 ). (
-d6)
0.79 ( , J = 7.3 , 6 ); 1.31 ( , J = 7.3 , 4 ); 2.28
, J = 7.3 , 4 ); 2.42 ( , 2 ); 2.57 ( , 2 ); 6.80 ( ,
J = 8.6, 1.7 , 1H); 7.04 ( , J = 1.7 , 1 ); 7.12 ( ,
); 7.60 ( , 2 ); 7.72 ( , J = 8.6, 1.7 , 1 ); 7.98 ( ,
3H); 8.25 ( , 1H); 9.87 ( , 1H); 10.70 ( , 1H).
-d6)
2.06 ( , 6 ); 2.15 ( , J = 8.2 , 2 ); 2.52 ( , J = 8.2 ,
); 6.69 ( , J = 8.7 , 1H); 6.85 ( , 1H); 7.02 ( , 1 );
3369, 1473,
7.08 ( , J = 8.7 , 1 ); 7.67 ( , 2 ); 7.84 ( , J = 7.3 ,
201-203
1161, 1125,
); 8.10 ( , J = 7.3 , 1 ); 8.41 ( , J = 8.4 , 1 );
1017, 789, 619
8.79 ( , J = 8.7 , 1 ); 10.15 ( , 1H); 10.70 ( , 1 ).
-d6)
3399, 3255, 2.03 ( , 6 ); 2.22 ( , J = 8.2 , 2 ); 2.58 ( , J = 8.2 ,
2943, 1466,
); 6.80 ( , J = 8.4 , 1H); 7.04 ( , 1H); 7.07 ( , 1 );
180-190
1330, 1156, 7.13 ( , J = 8.6 , 1H); 7.60 ( , 2 ); 7.74 ( , J = 8.6
1131, 1075,
, 1 ); 7.95 ( , J = 7.7 , 1H); 8.02 ( , 2 ); 8.26 ( ,
659, 550
); 9.86 ( , 1H); 10.71 ( , 1 ). (
-d6)
BY 10373 C1 2008.02.28
45
3386, 2929,
1466, 1157,
201-203
1106, 1080,
992, 861, 650,
564
3354, 2964,
2812, 1466,
212-214
1201, 1157,
1124, 808, 773,
593
3375, 2968,
2821, 1467,
1323, 1313,
180-182
1146, 1139,
113, 1079, 972,
654, 549
3398, 3255,
2958, 2931,
58-64
2872, 1466,
.)
1330, 1156,
1130, 1074,
659, 551
1
.
. R
1
R
2
n
R
3
A
.,
-1
(300
), δ (
)
°C
50
H
O
N
N
2
H
N
2
-
-
21
52
H
H3C N
2
H
-
Cl
53
H
H3C N
2
H
-
246-249
3329, 2940,
2916, 1470,
1158, 1125,
1110, 1015,
791, 598
2.29 ( , 6 ); 2.54 ( , 2 ); 3.57 ( , 4 ); 6.72 ( ,
J = 8.1 , 1H); 7.01 ( , 3H); 7.60 ( , J = 7.7 , 1 );
7.74 ( , J = 8.4 , 1 ); 8.19 ( , 2 ); 8.52 ( ,
J = 8.4 , 1 ); 9.21 ( , 1 ); 9.44 ( , 1 ); 10.65 ( , 1 ).
-d6)
2.29 ( , 6 ); 2.66 ( , 2 ); 3.47 ( , 4 ); 6.84 ( ,
J = 8.6 , 1 ); 7.07 ( , 1 ); 7.09 ( , 1H); 7.18 ( ,
J = 8.4 , 1H); 7.45 ( , 3H); 7.70 ( , 4 ); 7.79 ( , 2 );
9.79 ( , 1 ); 10.77 ( , 1 ). (
-d6)
1.40-1.60 ( , 4 ); 1.83 ( , 2 ); 2.14 ( , 3H); 2.36 ( ,
); 2.67 ( , J = 11.2 , 2 ); 6.78 ( , J = 8.4 , 1 );
6.97 ( , 1 ); 7.00 ( , 1H); 7.12 ( , J = 8.6 , 1H); 7.507.68 ( , 2 ); 7.73 ( , J = 9.0 , 1H); 8.00 ( , 3H);
8.23 ( , 1H); 9.78 ( , 1H); 10.71 ( , 1 ). (
-d6)
1.35-1.47 ( , 4 ); 1.86 ( , 2 ); 2.17 ( , 3H); 2.28 ( ,
); 2.76 ( , J = 10.6 , 2 ); 6.68 ( , J = 8.8 , 1 );
6.75 ( , 1H); 6.94 ( , 1H); 7.08 ( , J = 9.0 , 1 ); 7.607.73 ( , 2 ); 7.85 ( , J = 7.1 , 1H); 8.06 ( , J = 7.1
, 1H); 8.40 ( , J = 7.9 , 1 ); 8.79 ( , J = 9.0 ,
); 10.20 ( , 1H); 10.68 ( , 1 ). (
-d6)
BY 10373 C1 2008.02.28
51
O
3400, 3279,
2913, 2852,
234-235
1464, 1420,
1315, 1163,
1118, 951, 592
3340, 2857,
1479, 1324,
225-228
1153, 1116,
1094, 768, 670,
588
3367, 2924,
2852, 2799,
129-131
1465,1311,
1154, 1130,
1077, 666, 557
BY 10373 C1 2008.02.28
5-HT6
-293
,
5-
,
6
-
.
2,18
,
9,17
.
.L. Roth et at.
.L. Roth, S. . Craigo, M.S. Choudhary, A. Uluer, F.J. Monsma, Y. Shen, H.Y. Meltzer,
D.R. Sibley: Binding of Typical and Atypical Antipsychotic Agents to 5-Hydroxytryptamine-6
and Hydroxytriptamine-7 Receptors. The Journal of Pharmacology and Experimental Therapeutics, 1994, 268, 1403]
.
(1:40
)
: 50
-HCl, 10
MgCl2, 0,5
EDTA
3
(pH 7,4).
[ H]-LSD
2,7
200
.
100
(≈ 22,9
)
60
37 ° .
Brandel Cell Harvester
,
Schleicher
& Schuell GF 3362,
0,5 %
.
Tris-HCI 50
pH 7,4.
5
Ecoscint
.
Wallac Winspectral 1414.
100
.
( i,
)
,
EBDA/LIGAND [Munson and Rodbard, Analytical Bio.
.
,
chemistry, 1980, 107, 220].
10-6
%
1
3
4
5
6
7
8
9
11
13
14
15
16
17
Ki ( )
0,28
3,5
9,3
1,0
8,7
0,13
0,76
2,2
0,98
4,7
24,3
6,8
21,2
5,3
98,1 ± 4,0
96,6 ± 5,2
96,2 ± 0,6
101,2 ± 0,1
97,6 ± 1,8
103,0 ± 7,9
94,5 ± 7,0
96,8 ± 3,7
101,3
98,3
95,7 ± 3,4
97,4 ± 0,8
94,4 ± 8,6
102,0
1
,
-
.
,
,
- 500
,
,
,
,
I)
1
40-99
60
,
.
.%
( ,
.%
.
,
.
22
BY 10373 C1 2008.02.28
:
1
5
60
25
5
3
1
1
100
90
.
220034, .
,
.
, 20.
23
.
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