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US4591637A Expired / Lapsed US ⏱️ 0.0 years remaining

Open chain-morpholino adriamycins

Assignee: SRI International Inc
•
Filing: 1985-01-17
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Granted: 1986-05-27
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Expires: 2005-01-17
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Abstract

Abstract Compounds of the formula <IMAGE> and the pharmaceutically acceptable salts thereof wherein R is: -CO-CH3, -CHOH-CH3, -CO-CH2OH, -CHOH-CH2OH, hydrogen, hydroxy, 1 to 3 carbon alkyl, 1 to 3 carbon terminal hydroxyalkyl; or, a 2 to 7 carbon ester or diester of said -CO-CH2OH, -CHOH-CH2OH, -CHOH-CH3 or of said 1 to 3 carbon terminal hydroxyalkyl; or said -CO-CH2OH, -CHOH-CH2OH, or -CHOH-CH3 or said 1 to 3 C-terminal hydroxyalkyl having 1 to 6 carbon alkyl or aryl ether replacements of one or more of the hydroxyls; or the 13-ketimine derivatives of -CO-CH3 and -CO-CH2OH; Y is hydrogen, hydroxy, or methoxy, X is O or NH, but when Y is hydrogen or hydroxy, X must be O; at least one of R1 and R2 is hydrogen and the other is hydrogen, hydroxy, or methoxyl; B is H, alkyl or optionally substituted aryl lower alkyl, said alkyl or optionally substituted aryl lower alkyl also optionally containing hydroxy, alkoxy, carbonyl, cyano or ester group substitutions; or B and R2 taken together, in order, are the methylene-oxygen bridge -CH2-O-; and A is -CHR3CN wherein R3 is H, optionally substituted aryl, alkyl or optionally substituted aryl lower alkyl, said alkyl or optionally substituted aryl lower alkyl optionally containing hydroxy, alkoxy, carbonyl, or ester group substitutions are disclosed. These compounds are useful anti-tumor agents.

Inventors

  • 👤 Edward M. Acton
  • 👤 George L. Tong

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 13:15
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/20; C07H15/24; C07H15/252

Claims Analysis

Total Claims: 6
Claim 1
Independent Claim 306 words
A compound of the formula: ##STR4## and the pharmaceutically acceptable salts thereof wherein R is: --CO--CH 3 , --CHOH--CH 3 , --CO--CH 2 OH, --CHOH--CH 2 OH, hydrogen, hydroxy, 1 to 3 carbon alkyl, 1 to 3 carbon terminal hydroxyalkyl; or, a 2 to 7 carbon ester or diester of said --CO--CH 2 OH, --CHOH--CH 2 OH, --CHOH--CH 3 or of said 1 to 3 carbon terminal hydroxyalkyl; or said --CO--CH 2 OH, --CHOH--CH 2 OH, or --CHOH--CH 3 or said 1 to 3 C-terminal hydroxyalkyl having 1 to 6 carbon alkyl or aryl ether replacements of one or more of the hydroxyls; or 13-ketimine derivatives of --CO--CH 3 and --CO--CH 2 OH; Y is hydrogen, hydroxy, or methoxy, X is O or NH, but when Y is hydrogen or hydroxy, X must be O; at least one of R 1 and R 2 is hydrogen and the other is hydrogen, hydroxy, or methoxy; B is H, alkyl (1-6) or aryl (6-15) which is unsubstituted or which contains substituents selected from the group consisting of halo, lower alkyl (1-4) nitro or lower alkoxy; lower alkyl (1-4), said alkyl or said unsubstituted or substituted aryl lower alkyl also being unsubstituted or substituted with hydroxy, alkoxy, carbonyl, cyano or ester group substitutions; or B and R 2 taken together, in order, are the methylene-oxygen bridge --CH 2 --O--; and A is --CHR 3 CN wherein R 3 is H, aryl (6-15), which is unsubstituted or which contains substituents selected from the group consisting of halo, lower alkyl (1-4) nitro or lower alkoxy; alkyl (1-6) or aryl lower alkyl (1-4), wherein the aryl is unsubstituted or contains substituents selected from the group consisting of halo, lower alkyl (1-4) nitro or lower alkoxy; said alkyl or aryl lower alkyl is unsubstituted or contains hydroxy, alkoxy, carbonyl, or ester group substitutions.
Claim 2
Dependent Claim 306 words
A compound of the formula: ##STR4## and the pharmaceutically acceptable salts thereof wherein R is: --CO--CH 3 , --CHOH--CH 3 , --CO--CH 2 OH, --CHOH--CH 2 OH, hydrogen, hydroxy, 1 to 3 carbon alkyl, 1 to 3 carbon terminal hydroxyalkyl; or, a 2 to 7 carbon ester or diester of said --CO--CH 2 OH, --CHOH--CH 2 OH, --CHOH--CH 3 or of said 1 to 3 carbon terminal hydroxyalkyl; or said --CO--CH 2 OH, --CHOH--CH 2 OH, or --CHOH--CH 3 or said 1 to 3 C-terminal hydroxyalkyl having 1 to 6 carbon alkyl or aryl ether replacements of one or more of the hydroxyls; or 13-ketimine derivatives of --CO--CH 3 and --CO--CH 2 OH; Y is hydrogen, hydroxy, or methoxy, X is O or NH, but when Y is hydrogen or hydroxy, X must be O; at least one of R 1 and R 2 is hydrogen and the other is hydrogen, hydroxy, or methoxy; B is H, alkyl (1-6) or aryl (6-15) which is unsubstituted or which contains substituents selected from the group consisting of halo, lower alkyl (1-4) nitro or lower alkoxy; lower alkyl (1-4), said alkyl or said unsubstituted or substituted aryl lower alkyl also being unsubstituted or substituted with hydroxy, alkoxy, carbonyl, cyano or ester group substitutions; or B and R 2 taken together, in order, are the methylene-oxygen bridge --CH 2 --O--; and A is --CHR 3 CN wherein R 3 is H, aryl (6-15), which is unsubstituted or which contains substituents selected from the group consisting of halo, lower alkyl (1-4) nitro or lower alkoxy; alkyl (1-6) or aryl lower alkyl (1-4), wherein the aryl is unsubstituted or contains substituents selected from the group consisting of halo, lower alkyl (1-4) nitro or lower alkoxy; said alkyl or aryl lower alkyl is unsubstituted or contains hydroxy, alkoxy, carbonyl, or ester group substitutions.
Claim 3
Dependent Claim 21 words
The compound of claim 1 wherein R is COCH 3 , CHOHCH 3 , COCH 2 OH, or CHOHCH 2 OH.
Claim 4
Dependent Claim 35 words
The compound of claim 2 wherein Y is hydrogen, R 1 is hydrogen, and R 2 is OH or R 2 and B taken together in order are the methylene oxygen bridge --CH 2 --O--.
Claim 5
Dependent Claim 13 words
The compound of claim 2 wherein B is H or CHR 3 CN.
Claim 6
Dependent Claim 18 words
The compound of claim 4 which is selected from the group consisting of N-(cyanomethyl)daunorubicin, N(cyanomethyl)doxorubicin, N-(1-cyano-2-methoxyethyl)daunorubicin and N-(1-cyano-2-methoxyethyl)doxorubicin.

References Cited (Backward Citations)

US4177264A Cited
US4250303A Cited
US4477444A Cited
US4464529A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-05-26 1989-11-25 1990-05-27 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-05-26 1993-11-25 1994-05-27 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-05-26 1997-11-25 1998-05-27 $7700.00 Window Closed / Lapsed

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