180916. lajstromszámú szabadalom • Eljárás benzo [c] kinolin-származékok előállítására

23

180916

24

R R,

R,

RR<;

Z—W

6a, 10a

PBQ

TF

OH OH

ch3

H (CHdaCrfls-0-CH(CH3) (CH2)3C6H5

transz

29 e 10

OH COCH3

n-CsH;

H

H-0-CH(CH3) (CH2)3C6H5

transz

0,38

2,37

OH COCH3

n-C3H7

H

H-0-CH(CH3) (CH2)3C6H5

cisz

0,16

1,76

OH COCH3

ch3

H

H-0-CH(CH3) (CH2)3C6H3

cisz(a)

25 e 10

OH COCH3

ch3

H

H-O-CH(CHj) (CH2)3C6H5

cisz(b)

0,62

OH COCH3

ch3

H

H-0-CH(CH3) (CH2)3C6H5

transz(a)

2,11

OH COCH3

ch3

H

H-0-CH(CH3) (CH2)3C6H3

transz(b)

7,28

OH COCH3

C2H5

H

H-0-CH(CH3) (CH2)3C6H5

cisz

0,17

0,78

OH COCH3

CgHj;,

H

H-0-CH(CH3) (CH2)3C6H3

transz

35 e 10

OH COCH3

C2H5

H

H-0-CH(CH3) (CH2)3C6H5

transz

1,60

OH COCH3

CeH13

H

H-0-CH(CH3) (CH2)3C6H5

cisz

21 e 10

OH COCH3

-C6H5(CH2)2

H

H-0-CH(CH3) (CH2)3C6H5

transz

100 e 10

OH COCH3

-C6H3(CH2)2

H

H-0-CH(CH3) (CH2)3CgH5

cisz

34 e 10

OH COCH3

ch3

H

H-0(CH2)3C6H5

transz

22 e 56

OH COCH3

ch3

H

H-0(CH2)3C6H5

cisz

12 e 56

OH COCH3

CsHh

H

H-0-CH(CH3) (CH^CfiH

transz

14 e 10

OH COCH3

CgHu

H

H-0-CH(CH3) (CH2)3C6H5

cisz

14 e 10

OH COCH3

C/,H<)

H

H-0-CH(CH3) (CH2)3C6H5

transz

4,36

OH COCH3

C/,H.)

H

H-0-CH(CH3) (CH2)3C6H5

cisz

16 e 10

(a) =6

S, 6aR, 9R, lOaR

(b) =6R, 6aS, 9S, lOaS

HP

83 10

1,62

A XXf általános képletű benzo[c]kinolin-származékok gátló hatása a 3H-dihidro-morfinoknak ópiátreceptorokhoz kapcsolódására

gátló

R

Ri

R-,

R5

Ri;

H

Z—W

HA

hatás (n/o)

ß-OH

COCH,

CH:,

H

H

a-H

a

HC1

31

ß-OH

COCH:J

CH,

H

H

ß-H

a

HC1

59

ß-OH

H

CH;,

H

H

a-H

a

HC1

20

ß-OH

COCH:,

CH;,

H

ch3

a-H

a

HC1

12

ß-OH

COCH3

H

H

H

a-H

a

—

9

ß-OH

coch3

CH.,

H

H

a-H

b

HC1

19

ß-OH

coch3

CH,

H

CH,

a-H

b

—

11

a-OH

coch3

H

H

CH

a-H

a

HC1

44

ß-OH

CO(CH2)3-CH;,

H

H

a-H

a

2HC1

78

piperidino

ß-OH

COCH3

H

ch3

H

a-H

a

HC1

19

a-OH

coch3

CH,

H

H

ß-H

a

HC1

35

ß-OH

coch3

n-CjH;

H

H

a-H

a

HC1

28

ß-OH

COCH;,

n-C.H?

H

H

ß-H

a

HC1

23

ß-OH

H

CH;,

H

(CH2):,CüH5

a-H

a

HC1

—3

ß-OH

H

CH;;

H

n-C3Hj

a-H

a

HC1

19

ß-OH

H

CH;;

H

n-CfiH,;,

a-H

a

HC1

4

ß-OH

H

CH;

H

n-CjH,,

a-H

a

HC1

19

ß-OH

H

CH.;

H

(CH2)/,CgH

a-H

a

HC1

—4

ß-OH

H

CH;

H

n-C,Hj

a-H

a

HC1

7

ß-OH

H

CH,

H

CH3

a-H

a

HC1

8

ß-OH

COCH3

c,h5

H

H

a-H

a

HC1

53

ß-OH

coch3

n-CiHi;i

H

H

a-H

a

HC1

9

a-OH

COCH;,

CH;

H

CH;,

a-H

a

HC1

52

ß-OH

coch3

CH,

H

ch3

ß-H

a

HC1

39

ß-OH

COCH3

(CH2)C(iH)

H

H

a-H

a

HC1

3

ß-OH

CO(CH2).,COOH

CH;

H

H

a-H

a

HC1

17

ß-OH

CÓCH3

CH;,

H

H

a-H

c

HC1

9

/?-COCH3

coch3

CH;

H

H

~H

c

—

—5

ß-CH2OH

H

CH;

H

c2h

a-H

a

HC1

23

a-CH2OH

H

CH.,

H

C2H5

a-H

a

HC1

27

a-CH2OH

H

CH:i

H

COCH;,

a-H

a

—

44

ß-OH2OH

H

CH,

H

COCH;,

a-H

a

—

89

a-CH2OH

H

CH,

H

COCH;,

ß-H

a

—

89

ß-CHiPH

H

CH;,

H

COCH,

ß-H

a

—

88

12