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US4585859A Expired / Lapsed US ⏱️ 0.0 years remaining

Analogues of morpholinyl daunorubicin and morpholinyl doxorubicin

Assignee: SRI International Inc
•
Filing: 1984-04-09
•
Granted: 1986-04-29
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Expires: 2004-04-09
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Abstract

Abstract A group of new daunorubicin and doxorubicin derivatives is disclosed. Included in this group are 3'-deamino-3'(3''-cyano-4''-morpholinyl doxorubicin; 3'-deamino-3'-(3''-cyano-4''-morpholinyl)-13-dihydoxorubicin; (3'-deamino-3'-(3''-cyano-4''-morpholinyl) daunorubicin; 3'-deamino-3'-(3''-cyano-4''-morpholinyl)-3-dihydrodaunorubicin; and 3'-deamino-3'-(4''-morpholinyl-5-iminodoxorubicin and derivatives thereof which have excellent activity as antitumor agents.

Inventors

  • 👤 Carol W. Mosher
  • 👤 George L. Tong
  • 👤 Edward M. Acton

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 10:15
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/20; C07H15/24; C07H15/252; A; A61; A61P; A61P35/00

Claims Analysis

Total Claims: 9
Claim 1
Independent Claim 183 words
A compound of the formula ##STR17## wherein R is --CO--CH 3 , --CHOH--CH 3 , --CO--CH 2 OH, or --CHOH--CH 2 OH; hydroxy; a 1 to 3 carbon alkyl; a 1 to 3 carbon terminal hydroxyalkyl; a 2 to 7 carbon organic acid ester or diester of --CO--CH 2 OH, --CHOH--CH 2 OH, or --CHOH--CH 3 ; the groups --COCH 2 OH, --CHOHCH 2 OH or --CHOHCH 3 having a 1 to 6 carbon alkyl or aryl ether replacement of one or more hydroxyls; or 13-ketimine derivative of --CO--CH 3 or --CO--CH 2 OH; Y is methoxy or hydrogen; X is ═O or ═NH; R' and R" together are a hydrogen and a hydroxy, both are hydrogens, or R' is O-methoxy and R" is hydrogen; B is CN, or B and the hydrogen bonded to the same carbon taken together are ═O; or B and R' taken together are the oxygen bridge --O--; and A is cyano; Z is oxygen, sulfur, CH 2 , or ##STR18## wherein R'" is a 1 to 3 carbon alkyl, and the pharmaceutically acceptable acid addition salts therof.
Claim 2
Dependent Claim 183 words
A compound of the formula ##STR17## wherein R is --CO--CH 3 , --CHOH--CH 3 , --CO--CH 2 OH, or --CHOH--CH 2 OH; hydroxy; a 1 to 3 carbon alkyl; a 1 to 3 carbon terminal hydroxyalkyl; a 2 to 7 carbon organic acid ester or diester of --CO--CH 2 OH, --CHOH--CH 2 OH, or --CHOH--CH 3 ; the groups --COCH 2 OH, --CHOHCH 2 OH or --CHOHCH 3 having a 1 to 6 carbon alkyl or aryl ether replacement of one or more hydroxyls; or 13-ketimine derivative of --CO--CH 3 or --CO--CH 2 OH; Y is methoxy or hydrogen; X is ═O or ═NH; R' and R" together are a hydrogen and a hydroxy, both are hydrogens, or R' is O-methoxy and R" is hydrogen; B is CN, or B and the hydrogen bonded to the same carbon taken together are ═O; or B and R' taken together are the oxygen bridge --O--; and A is cyano; Z is oxygen, sulfur, CH 2 , or ##STR18## wherein R'" is a 1 to 3 carbon alkyl, and the pharmaceutically acceptable acid addition salts therof.
Claim 3
Dependent Claim 20 words
The compound of claim 1 wherein R is COCH 3 , COCH 2 OH, --CHOHCH 3 or --CHOHCH 2 OH.
Claim 4
Dependent Claim 9 words
The compound of claim 2 which is 3'-deamino-3'-(3"-cyano-5"-oxo-4"-morpholinyl) doxorubicin.
Claim 5
Dependent Claim 9 words
The compound of claim 2 which is 3'deamino-3'-(3",5"-dicyano-4"-morpholinyl) doxorubicin.
Claim 6
Dependent Claim 9 words
The compound of claim 2 which is 3'deamino-4',5"-anhydro-3'-(3"-cyano-5"-hydroxy-4"-morpholinyl) doxorubicin.
Claim 7
Dependent Claim 9 words
The compound of claim 2 which is 3'deamino-3'-(3"-cyano-5"-oxo-4"-morpholinyl) daunorubicin.
Claim 8
Dependent Claim 9 words
The compound of claim 2 which is 3'deamino-3'-(3",5"-dicyano-4"morpholinyl) daunorubicin.
Claim 9
Dependent Claim 9 words
The compound of claim 2 which is 3'deamino-4',5"-anhydro-3'-(3"-cyano-5"-hydroxy-4"-morpholinyl) daunorubicin.

References Cited (Backward Citations)

US4202967A Cited
US4301277A Cited
US4314054A Cited
US4464529A Cited
EP0128670A1 Cited
GB2140006A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-04-28 1989-10-28 1990-04-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-04-28 1993-10-28 1994-04-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-04-28 1997-10-28 1998-04-29 $7700.00 Window Closed / Lapsed

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