US5086059A
Expired / Lapsed
US
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Bis-naphthalimides as anticancer agents
Assignee: Bristol Myers Squibb Pharma Co
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Filing: 1990-06-07
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Granted: 1992-02-04
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Expires: 2010-06-07
Abstract
Abstract There are provided novel bis-napthalimide compounds useful as antitumor agents, pharmaceutical compositions containing them and processes for preparing intermediates to such compounds.
Inventors
- 👤 Robert J. Ardecky
- 👤 Arthur D. Patten
- 👤 Jung-Hui Sun
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 19:38
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/08; C07D211/18; C07D221/00; C07D221/02; C07D221/04; C07D221/18; A; A61; A61P; A61P35/00
Claims Analysis
Total Claims: 37
Claim 1
Independent Claim
203 words
A compound of the formula: ##STR12## or a pharmaceutically acceptable salt thereof, wherein: A is RN(CH 2 ) n NR' or NR 1 (n=2-10); R, R' and R 1 independently are H, C 1 -C 6 alkyl, benzyl optionally substituted with 1 or more substituents independently selected from the group consisting of: H, C 1 -C 6 alkyl, halogen, CF 3 , NO 2 , OH, N(R 2 ) 2 , OR 3 , CO 2 R 4 , CONR 5 , NHCOR 6 , SO 2 NR 7 or S(O) t R 8 , (t is 0, 1 or 2); R 2 , R 5 and R 7 independently are H, C 1 -C 3 alkyl including cyclopropyl; R 3 and R 4 independently are H or C 1 -C 6 alkyl; R 6 and R 8 independently are C 1 -C 6 alkyl; X, X', Y and Y' independently are selected from the group consisting of: H, NO 2 , N(R 9 ) 2 , halogen or OR 10 ; R 9 and R 10 independently are H Or C 1 -C 6 alkyl; each α is independently a single or a double bond; and m and p independently are 2-10.
Claim 2
Dependent Claim
203 words
A compound of the formula: ##STR12## or a pharmaceutically acceptable salt thereof, wherein: A is RN(CH 2 ) n NR' or NR 1 (n=2-10); R, R' and R 1 independently are H, C 1 -C 6 alkyl, benzyl optionally substituted with 1 or more substituents independently selected from the group consisting of: H, C 1 -C 6 alkyl, halogen, CF 3 , NO 2 , OH, N(R 2 ) 2 , OR 3 , CO 2 R 4 , CONR 5 , NHCOR 6 , SO 2 NR 7 or S(O) t R 8 , (t is 0, 1 or 2); R 2 , R 5 and R 7 independently are H, C 1 -C 3 alkyl including cyclopropyl; R 3 and R 4 independently are H or C 1 -C 6 alkyl; R 6 and R 8 independently are C 1 -C 6 alkyl; X, X', Y and Y' independently are selected from the group consisting of: H, NO 2 , N(R 9 ) 2 , halogen or OR 10 ; R 9 and R 10 independently are H Or C 1 -C 6 alkyl; each α is independently a single or a double bond; and m and p independently are 2-10.
Claim 3
Dependent Claim
13 words
A compound of claim 1 wherein A is RN(CH 2 ) n NR'.
Claim 4
Dependent Claim
16 words
A compound of claim 1 wherein R and R' are C 1 to C 6 alkyl.
Claim 5
Dependent Claim
9 words
A compound of claim 1 wherein n is 2-6.
Claim 6
Dependent Claim
9 words
A compound of claim 2 wherein n is 2-6.
Claim 7
Dependent Claim
12 words
A compound of claim 1 wherein m and p independently are 2-6.
Claim 8
Dependent Claim
13 words
A compound of claim 1 wherein X, X', Y and Y' are H.
Claim 9
Dependent Claim
12 words
A compound of claim 1 wherein each α is a single bond.
Claim 10
Dependent Claim
46 words
A compound of claim 1 wherein: A is RN(CH 2 ) n NR'; R and R' are independently C 1 -C 6 alkyl; n is 2-6; m and p are independently 2-6; X, X', Y and Y' are H; and each α is a single bond.
Claim 11
Dependent Claim
17 words
The compound of claim 1 which is 1,4-Bis-[3-(1,3,6,7-tetrahydro-1,3-dioxo-2H-indeno[6,7,1-def]isoquinoline-2-yl)propyl-amino]butane, or the dihydromethane sulfonate salt or dihydrochloride salt thereof.
Claim 12
Dependent Claim
13 words
The compound of claim 1 which is 1,4-Bis[3-(1,3,6,7-tetrahydro-1,3-dioxo-2H-indeno[6,7,1-def]isoquinoline-2-yl)-N-ethyl-propylamino]butane, or the dihydrochloride salt thereof.
Claim 13
Dependent Claim
13 words
The compound of claim 1 which is 4-[3-(1,3,6,7-tetrahydro-1,3-dioxo-2H-indeno[6,7,1-def]isoquinoline-2-yl)propyl-amino]-1-(1,3,6,7-tetrahydro-1,3-dioxo-2H-indeno-[6,7,1-def]isoquinoline-2-yl)butane, or the methanesulfonate salt thereof.
Claim 14
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 1.
Claim 15
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 2.
Claim 16
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 3.
Claim 17
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 4.
Claim 18
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 5.
Claim 19
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 6.
Claim 20
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 7.
Claim 21
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 8.
Claim 22
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of a compound of claim 9.
Claim 23
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of the compound of claim 10.
Claim 24
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of the compound of claim 11.
Claim 25
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically acceptable carrier and a therapeutically effective amount of the compound of claim 12.
Claim 26
Dependent Claim
25 words
A method of treating a B16F10 melanoma tumor in a mammal comprising administering to the mammal bearing such tumor, a tumor-inhibiting amount of claim 1.
Claim 27
Dependent Claim
25 words
A method of treating a B16F10 melanoma tumor in a mammal comprising administering to the mammal bearing such tumor, a tumor-inhibiting amount of claim 2.
Claim 28
Dependent Claim
25 words
A method of treating a B16F10 melanoma tumor in a mammal comprising administering to the mammal bearing such tumor, a tumor-inhibiting amount of claim 3.
Claim 29
Dependent Claim
25 words
A method of treating a B16F10 melanoma tumor in a mammal comprising administering to the mammal bearing such tumor, a tumor-inhibiting amount of claim 4.
Claim 30
Dependent Claim
25 words
A method of treating a B16F10 melanoma tumor in a mammal comprising administering to the mammal bearing such tumor, a tumor-inhibiting amount of claim 5.
Claim 31
Dependent Claim
25 words
A method of treating a B16F10 melanoma tumor in a mammal comprising administering to the mammal bearing such tumor, a tumor-inhibiting amount of claim 6.
Claim 32
Dependent Claim
25 words
A method of treating a B16F10 melanoma tumor in a mammal comprising administering to the mammal bearing such tumor, a tumor-inhibiting amount of claim 7.
Claim 33
Dependent Claim
25 words
A method of treating a B16F10 melanoma tumor in a mammal comprising administering to the mammal bearing such tumor, a tumor-inhibiting amount of claim 8.
Claim 34
Dependent Claim
25 words
A method of treating a B16F10 melanoma tumor in a mammal comprising administering to the mammal bearing such tumor, a tumor-inhibiting amount of claim 9.
Claim 35
Dependent Claim
25 words
A method of treating a B16F10 melanoma tumor in a mammal comprising administering to the mammal bearing such tumor, a tumor-inhibiting amount of claim 10.
Claim 36
Dependent Claim
25 words
A method of treating a B16F10 melanoma tumor in a mammal comprising administering to the mammal bearing such tumor, a tumor-inhibiting amount of claim 11.
Claim 37
Dependent Claim
25 words
A method of treating a B16F10 melanoma tumor in a mammal comprising administering to the mammal bearing such tumor, a tumor-inhibiting amount of claim 12.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-02-03 | 1995-08-05 | 1996-02-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-02-03 | 1999-08-05 | 2000-02-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-02-03 | 2003-08-05 | 2004-02-04 | $7700.00 | Window Closed / Lapsed |