US4785085A
Expired / Lapsed
US
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Rebeccamycin analogs
Assignee: Bristol Myers Co
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Filing: 1986-11-21
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Granted: 1988-11-15
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Expires: 2006-11-21
Abstract
Abstract There are disclosed analogs of the antitumor agent, rebeccamycin, which possess antineoplastic properties against mammalian, particularly experimental animal, tumor systems. The compounds of the invention are aminoalkylated derivatives of rebeccamycin produced by first reacting rebeccamycin with a strong base to obtain a reactive intermediate and then reacting the reactive intermediate with an aminoalkyl compound.
Inventors
- 👤 Takushi Kaneko
- 👤 Henry S. Wong
- 👤 Jacob J. Utzig
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 22:43
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/12; C07D487/14; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/044; A; A61; A61P; A61P35/00; C07H19/23
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
256 words
A compound having the formula ##STR6## wherein: n is an integer from 1 to 6; A 6 and A 13 are selected from H and --(CH 2 ) n NR 1 R 2 and at least one of A 6 and A 13 is --(CH 2 ) n --NR 1 R 2 ; R 1 and R 2 , independently, are selected from hydrogen, unsubstituted and substituted C 1 -C 6 alkyl, aralkyl having 1 to 3 carbons in the alkyl moiety and unsubstituted phenyl or phenyl substituted with 1 to 3 alkyl, alkoxy, hydroxy, halo, carboxyl, alkoxycarbonyl, and amino and mono- and di-lower-alkylamino groups in the aryl moiety, and aryl selected from unsubstituted phenyl and phenyl substituted with 1 to 3 alkyl, alkoxy, hydroxy, halo, amino, mono- and dialkylamino, nitro, carboxyl, alkoxycarbonyl, and cyano groups provided that both R 1 and R 2 are not each aryl and, when taken together, R 1 and R 2 may be selected from --(CH 2 ) 4 -- and (CH 2 ) 2 --R 3 --(CH 2 ) 2 -- to form a 5- or 6-membered ring together with the N-atom wherein R 3 is selected from CH 2 , NH, O and S; X is selected from H, F, Cl, Br, C 1 -C 3 alkyl, OH, carboxyl, alkoxycarbonyl and alkoxy wherein the alkyl moiety is C 1 -C 3 alkyl, benzyloxy, amino, and mono- and dialkylamino; and R 4 is selected from H and CH 3 ; and pharmaceutically acceptable acid addition and base salts thereof.
Claim 2
Dependent Claim
256 words
A compound having the formula ##STR6## wherein: n is an integer from 1 to 6; A 6 and A 13 are selected from H and --(CH 2 ) n NR 1 R 2 and at least one of A 6 and A 13 is --(CH 2 ) n --NR 1 R 2 ; R 1 and R 2 , independently, are selected from hydrogen, unsubstituted and substituted C 1 -C 6 alkyl, aralkyl having 1 to 3 carbons in the alkyl moiety and unsubstituted phenyl or phenyl substituted with 1 to 3 alkyl, alkoxy, hydroxy, halo, carboxyl, alkoxycarbonyl, and amino and mono- and di-lower-alkylamino groups in the aryl moiety, and aryl selected from unsubstituted phenyl and phenyl substituted with 1 to 3 alkyl, alkoxy, hydroxy, halo, amino, mono- and dialkylamino, nitro, carboxyl, alkoxycarbonyl, and cyano groups provided that both R 1 and R 2 are not each aryl and, when taken together, R 1 and R 2 may be selected from --(CH 2 ) 4 -- and (CH 2 ) 2 --R 3 --(CH 2 ) 2 -- to form a 5- or 6-membered ring together with the N-atom wherein R 3 is selected from CH 2 , NH, O and S; X is selected from H, F, Cl, Br, C 1 -C 3 alkyl, OH, carboxyl, alkoxycarbonyl and alkoxy wherein the alkyl moiety is C 1 -C 3 alkyl, benzyloxy, amino, and mono- and dialkylamino; and R 4 is selected from H and CH 3 ; and pharmaceutically acceptable acid addition and base salts thereof.
Claim 3
Dependent Claim
222 words
A compound according to claim 1 having the formula ##STR7## wherein: n is an integer from 1 to 6; R 1 and R 2 , independently, are selected from hydrogen, unsubstituted and substituted C 1 -C 6 alkyl, aralkyl having 1 to 3 carbons in the alkyl moiety and unsubstituted phenyl or phenyl substituted with 1 to 3 alkyl, alkoxy, hydroxy, halo, carboxyl, alkoxycarbonyl, and amino and mono- and di-lower-alkylamino groups in the aryl moiety, and aryl selected from unsubstituted phenyl and phenyl substituted with 1 to 3 alkyl, alkoxy, hydroxy, halo, amino, mono- and dialkylamino, nitro, carboxyl, alkoxycarbonyl, and cyano groups provided that both R 1 and R 2 are not each aryl and, when taken together, R 1 and R 2 may be selected from --(CH 2 ) 4 -- and (CH 2 ) 2 --R 3 --(CH 2 ) 2 -- to form a 5- or 6-membered ring together with the N-atom wherein R 3 is selected from CH 2 , NH, O and S; X is selected from H, F, Cl, Br, C 1 -C 3 alkyl, OH, carboxyl, alkoxycarbonyl and alkoxy wherein the alkyl moiety is C 1 -C 3 alkyl, benzyloxy, amino, and mono- and dialkylamino; and R 4 is selected from H and CH 3 ; and pharmaceutically acceptable acid addition and base salts thereof.
Claim 4
Dependent Claim
25 words
A compound according to claim 2 wherein X is selected from H, Cl, Br, OH, OCH 3 and OCH 2 C 6 H 5 .
Claim 5
Dependent Claim
40 words
A compound according to claim 3 wherein n is selected from the integers 1, 2, and 3 and R 1 and R 2 , independently, are selected from H, C 1 -C 3 alkyl, and --(CH 2 ) 4 --.
Claim 6
Dependent Claim
17 words
A compound according to claim 4 wherein X is Cl in each of the 1- and 11-positions.
Claim 7
Dependent Claim
29 words
A compound according to claim 5 wherein n is an integer selected from 2 and 3; and R 1 and R 2 are each C 2 H 5 .
Claim 8
Dependent Claim
218 words
A compound having the formula ##STR8## wherein: n is an integer from 1 to 6; R 1 and R 2 , independently, are selected from hydrogen, unsubstituted and substituted C 1 -C 6 alkyl, aralkyl having 1 to 3 carbons in the alkyl moiety and unsubstituted phenyl or phenyl substituted with 1 to 3 alkyl, alkoxy, hydroxy, halo, carboxyl, alkoxycarbonyl, and amino and mono- and di-lower-alkylamino groups in the aryl moiety, and aryl selected from unsubstituted phenyl and phenyl substituted with 1 to 3 alkyl, alkoxy, hydroxy, halo, amino, mono- and dialkylamino, nitro, carboxyl, alkoxycarbonyl, and cyano groups provided that both R 1 and R 2 are not each aryl and, when taken together, R 1 and R 2 may be selected from --(CH 2 ) 4 -- and --(CH 2 ) 2 --R 3 --(CH 2 ) 2 -- to form a 5- or 6-membered ring together the N-atom wherein R 3 L is selected from CH 2 , NH, O and S; X is selected from H, F, Cl, Br, C 1 -C 3 alkyl, OH, carboxyl, alkoxycarbonyl and alkoxy wherein the alkyl moiety is C 1 -C 3 alkyl, benzyloxy, amino, and mono- and dialkylamino; and R 4 is selected from H and CH 3 ; and pharmaceutically acceptable acid addition and base salts thereof.
Claim 9
Dependent Claim
218 words
A compound having the formula ##STR8## wherein: n is an integer from 1 to 6; R 1 and R 2 , independently, are selected from hydrogen, unsubstituted and substituted C 1 -C 6 alkyl, aralkyl having 1 to 3 carbons in the alkyl moiety and unsubstituted phenyl or phenyl substituted with 1 to 3 alkyl, alkoxy, hydroxy, halo, carboxyl, alkoxycarbonyl, and amino and mono- and di-lower-alkylamino groups in the aryl moiety, and aryl selected from unsubstituted phenyl and phenyl substituted with 1 to 3 alkyl, alkoxy, hydroxy, halo, amino, mono- and dialkylamino, nitro, carboxyl, alkoxycarbonyl, and cyano groups provided that both R 1 and R 2 are not each aryl and, when taken together, R 1 and R 2 may be selected from --(CH 2 ) 4 -- and --(CH 2 ) 2 --R 3 --(CH 2 ) 2 -- to form a 5- or 6-membered ring together the N-atom wherein R 3 L is selected from CH 2 , NH, O and S; X is selected from H, F, Cl, Br, C 1 -C 3 alkyl, OH, carboxyl, alkoxycarbonyl and alkoxy wherein the alkyl moiety is C 1 -C 3 alkyl, benzyloxy, amino, and mono- and dialkylamino; and R 4 is selected from H and CH 3 ; and pharmaceutically acceptable acid addition and base salts thereof.
Claim 10
Dependent Claim
40 words
A compound according to claim 7 wherein R 4 is CH 3 and X is selected from Cl, Br, OH, OCH 3 and OCH 2 C 6 H 5 in each of the 1- and 11-positions of the ring system.
Claim 11
Dependent Claim
40 words
A compound according to claim 8 wherein n is selected from the integers 1, 2, and 3 and R 1 and R 2 , independently, are selected from H, C 1 -C 3 alkyl, and --(CH 2 ) 4 --.
Claim 12
Dependent Claim
17 words
A compound according to claim 9 wherein X is Cl in each of the 1- and 11-positions.
Claim 13
Dependent Claim
29 words
A compound according to claim 10 wherein n is an integer selected from 2 and 3; and R 1 and R 2 are each C 2 H 5 .
References Cited (Backward Citations)
US4487925A
Cited
US4552842A
Cited
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