Patent US2923378A successfully refreshed from Google Patents.
US4014883A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Indoloquinolines, intermediates and processes
Assignee: Hoffmann La Roche Inc
•
Filing: 1975-07-16
•
Granted: 1977-03-29
•
Expires: 1995-07-16
Abstract
Abstract Derivatives of 7H-indolo[2,3-c]quinolin-6(5H)-one and 7H-indolo[2,3-c]quinoline, prepared, inter alia, from the corresponding 3-azido-4-phenylcarbostyrils or corresponding N-(lower alkylamino)-3-(2-fluorophenyl)-indole-2-carboxamides, are described. The end products of the invention are useful as anti-tumor agents, i.e., they inhibit the growth of transplantable tumors.
Inventors
- 👤 Rodney Ian Fryer
- 👤 Robert Ye-Fong Ning
- 👤 Leo Henryk Sternbach
- 👤 Armin Walser
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 02:15
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/38; C07C; C07C251/00; C07C251/72; C07D209/00; C07D209/02; C07D209/04; C07D209/30; C07D209/42; C07D471/00; C07D471/02; C07D471/04
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
224 words
A compound of the formula ##STR31## wherein R 1 and R 5 / , independently, are hydrogen, halogen, trifluoromethyl, lower alkyl of 1 of 7 carbon atoms, lower alkoxy of 1 to 7 carbon atoms, amino, cyano or nitro; R 2 and R 4 , independently, are hydrogen, lower alkyl of 1 to 7 carbon atoms, cyano-lower alkyl wherein lower alkyl is of 1 to 7 carbon atoms, dihydroxy-lower alkyl of 1 to 7 carbon atoms, 2,3-epoxy-propyl, lower alkenyl of 2 of 7 carbon atoms, ##STR32## or -A--O-13 B, wherein A is a straight chain lower alkylene of 1-7 carbon atoms or a straight chain lower alkylene of 1 to 7 carbon atoms mono-substituted by lower alkyl of 1-7 carbon atoms, R 6 and R 7 , independently, are hydrogen, lower alkyl of 1 to 7 carbon atoms, hydroxy-lower alkyl of 1 to 7 carbon atoms or halo-lower alkyl of 1 to 7 carbon atoms, or taken together with the nitrogen atom, are piperidino, piperazino, pyrrolidino, morpholino, imidazoline, 4-lower alkylpiperazino wherein lower alkyl is of 1-7 carbon atoms or methylpiperidino, and B is hydrogen, lower alkyl of 1 to 7 carbon atoms or lower alkanoyl of 1 to 7 carbon atoms; provided that at least one of R 2 or R 4 is ##STR33## or an addition salt thereof with a pharmaceutically acceptable acid.
Claim 2
Dependent Claim
224 words
A compound of the formula ##STR31## wherein R 1 and R 5 / , independently, are hydrogen, halogen, trifluoromethyl, lower alkyl of 1 of 7 carbon atoms, lower alkoxy of 1 to 7 carbon atoms, amino, cyano or nitro; R 2 and R 4 , independently, are hydrogen, lower alkyl of 1 to 7 carbon atoms, cyano-lower alkyl wherein lower alkyl is of 1 to 7 carbon atoms, dihydroxy-lower alkyl of 1 to 7 carbon atoms, 2,3-epoxy-propyl, lower alkenyl of 2 of 7 carbon atoms, ##STR32## or -A--O-13 B, wherein A is a straight chain lower alkylene of 1-7 carbon atoms or a straight chain lower alkylene of 1 to 7 carbon atoms mono-substituted by lower alkyl of 1-7 carbon atoms, R 6 and R 7 , independently, are hydrogen, lower alkyl of 1 to 7 carbon atoms, hydroxy-lower alkyl of 1 to 7 carbon atoms or halo-lower alkyl of 1 to 7 carbon atoms, or taken together with the nitrogen atom, are piperidino, piperazino, pyrrolidino, morpholino, imidazoline, 4-lower alkylpiperazino wherein lower alkyl is of 1-7 carbon atoms or methylpiperidino, and B is hydrogen, lower alkyl of 1 to 7 carbon atoms or lower alkanoyl of 1 to 7 carbon atoms; provided that at least one of R 2 or R 4 is ##STR33## or an addition salt thereof with a pharmaceutically acceptable acid.
Claim 3
Dependent Claim
165 words
A compound of the formula ##STR34## wherein R 2 and R 4 , independently, are hydrogen, lower alkyl of 1 to 7 carbon atoms, hydroxy-lower alkyl of 1 to 7 carbon atoms, lower alkoxy of 1 to 7 carbon atoms, lower alkyl of 1 to 7 carbon atoms lower alkenyl of 2 to 7 carbon atoms or ##STR35## wherein A is a straight chain lower alkylene of 2-7 carbon atoms or straight chain lower alkylene of 2 to 7 carbon atoms mono- substituted by lower alkyl of 1 to 7 carbon atoms, and R 6 and R 7 , independently, are hydrogen or lower alkyl of 1 to 7 carbon atoms, or taken together with the nitrogen atom, are piperidino, piperazino, pyrrolidino, morpholino, imidazoline, 4-lower alkylpiperazino wherein lower alkyl is of 1-7 carbon atoms or methylpiperidino; and R 5 is nitro, halogen, or trifluoromethyl; provided that one of R 2 or R 4 is ##STR36## or an addition salt thereof with a pharmaceutically acceptable acid.
Claim 4
Dependent Claim
165 words
A compound of the formula ##STR34## wherein R 2 and R 4 , independently, are hydrogen, lower alkyl of 1 to 7 carbon atoms, hydroxy-lower alkyl of 1 to 7 carbon atoms, lower alkoxy of 1 to 7 carbon atoms, lower alkyl of 1 to 7 carbon atoms lower alkenyl of 2 to 7 carbon atoms or ##STR35## wherein A is a straight chain lower alkylene of 2-7 carbon atoms or straight chain lower alkylene of 2 to 7 carbon atoms mono- substituted by lower alkyl of 1 to 7 carbon atoms, and R 6 and R 7 , independently, are hydrogen or lower alkyl of 1 to 7 carbon atoms, or taken together with the nitrogen atom, are piperidino, piperazino, pyrrolidino, morpholino, imidazoline, 4-lower alkylpiperazino wherein lower alkyl is of 1-7 carbon atoms or methylpiperidino; and R 5 is nitro, halogen, or trifluoromethyl; provided that one of R 2 or R 4 is ##STR36## or an addition salt thereof with a pharmaceutically acceptable acid.
Claim 5
Dependent Claim
22 words
A compound is accordance with claim 2, wherein one of R 2 or R 4 is hydrogen and the other is ##STR37##
Claim 6
Dependent Claim
8 words
The compound in accordance with claim 3, 5-(2-dimethylaminoethyl)-7H-indolo[2,3-c]quinolin-6(5H)-one.
Claim 7
Dependent Claim
8 words
The compound in accordance with claim 3, 7-(2-diethylaminoethyl)-7H-indolo[2,3-c]quinolin-6(5H)-one.
Claim 8
Dependent Claim
12 words
A compound in accordance with claim 3, wherein R 5 is chloro.
Claim 9
Dependent Claim
8 words
The compound in accordance with claim 6, 10-chloro-5-(2-dimethylaminoethyl)-7H-indolo[2,3-c]quinolin-6(5H)-one.
Claim 10
Dependent Claim
8 words
The compound in accordance with claim 6, 10-chloro-5-(2-methylaminoethyl)-7H-indolo[2,3-c]quinolin-6(5H)-one.
Claim 11
Dependent Claim
8 words
The compound in accordance with claim 6, 10-chloro-5-(2-aminoethyl)-7H-indolo[2,3-c]quinolin-6(5H)-one.
Claim 12
Dependent Claim
8 words
The compound in accordance with claim 6, 10-chloro-7-(2-dimethylaminoethyl)-7H-indolo[2,3-c]quinolin-6(5H)-one.
Claim 13
Dependent Claim
387 words
A compound of the formula ##STR38## wherein R 1 is hydrogen, halogen, trifluoromethyl, lower alkyl of 1 to 7 carbon atoms, lower alkoxy of 1 to 7 carbon atoms, amino, cyano or nitro; R 3 is hydrogen, halogen, trifluoromethyl, hydrazino, lower alkyl of 1 to 7 carbon atoms, amino, lower alkylamino of 1 to 7 carbon atoms, di-lower alkylamino of 1 to 7 carbon atoms, lower alkoxy of 1 to 7 carbon atoms, lower alkoxyamino of 1 to 7 carbon atoms, ##STR39## wherein A is a straight chain lower alkylene of 2-7 carbon atoms or a straight-chain lower alkylene of 2 to 7 carbon atoms mono-substituted by lower alkyl of 1 to 7 carbon atoms, R 6 and R 7 , independently, are hydrogen, lower alkyl of 1 to 7 carbon atoms, hydroxy-lower alkyl of 1 to 7 carbon atoms or halo-lower alkyl of 1 to 7 carbon atoms, or taken together with the nitrogen atom, are piperidino, piperazino, pyrrolidino, morpholino, imidazoline, 4-lower alkylpiperazino wherein lower alkyl is of 1-7 carbon atoms or methylpiperidino, R 8 is hydrogen or lower alkyl of 1 to 7 carbon atoms and B is hydrogen, lower alkyl of 1 to 7 carbon atoms or lower alkanoyl of 1 to 7 carbon atoms; R 4 is hydrogen, lower alkyl of 1 to 7 carbon atoms, ##STR40## or -A-O-B, wherein A is a straight chain lower alkylene of 2-7 carbon atoms or a straight chain lower alkylene of 2-7 carbon atoms mono-substituted by lower alkyl of 1-7 carbon atoms, R 6 and R 7 , independently, are hydrogen, lower alkyl of 1 to 7 carbon atoms, hydroxy-lower alkyl of 1 to 7 carbon atoms or halo-lower alkyl of 1 to 7 carbon atoms, or taken together with the nitrogen atom, are piperidino, piperazino, pyrrolidino, morpholino, imidazoline, 4-lower alkylpiperazino wherein lower alkyl is of 1-7 carbon atoms an methylpiperidino, and B is hydrogen, lower alkyl of 1 to 7 carbon atoms or lower alkanoyl of 1 to 7 carbon atoms; and R 9 is halogen, lower alkyl of 1 to 7 carbon atoms, lower alkoxy of 1 to 7 carbon atoms, amino, cyano or nitro; provided that at least one of R 3 or R 4 is a basic amino side chain or --A--O--B, or an addition salt thereof with a pharmaceutically acceptable acid.
Claim 14
Dependent Claim
387 words
A compound of the formula ##STR38## wherein R 1 is hydrogen, halogen, trifluoromethyl, lower alkyl of 1 to 7 carbon atoms, lower alkoxy of 1 to 7 carbon atoms, amino, cyano or nitro; R 3 is hydrogen, halogen, trifluoromethyl, hydrazino, lower alkyl of 1 to 7 carbon atoms, amino, lower alkylamino of 1 to 7 carbon atoms, di-lower alkylamino of 1 to 7 carbon atoms, lower alkoxy of 1 to 7 carbon atoms, lower alkoxyamino of 1 to 7 carbon atoms, ##STR39## wherein A is a straight chain lower alkylene of 2-7 carbon atoms or a straight-chain lower alkylene of 2 to 7 carbon atoms mono-substituted by lower alkyl of 1 to 7 carbon atoms, R 6 and R 7 , independently, are hydrogen, lower alkyl of 1 to 7 carbon atoms, hydroxy-lower alkyl of 1 to 7 carbon atoms or halo-lower alkyl of 1 to 7 carbon atoms, or taken together with the nitrogen atom, are piperidino, piperazino, pyrrolidino, morpholino, imidazoline, 4-lower alkylpiperazino wherein lower alkyl is of 1-7 carbon atoms or methylpiperidino, R 8 is hydrogen or lower alkyl of 1 to 7 carbon atoms and B is hydrogen, lower alkyl of 1 to 7 carbon atoms or lower alkanoyl of 1 to 7 carbon atoms; R 4 is hydrogen, lower alkyl of 1 to 7 carbon atoms, ##STR40## or -A-O-B, wherein A is a straight chain lower alkylene of 2-7 carbon atoms or a straight chain lower alkylene of 2-7 carbon atoms mono-substituted by lower alkyl of 1-7 carbon atoms, R 6 and R 7 , independently, are hydrogen, lower alkyl of 1 to 7 carbon atoms, hydroxy-lower alkyl of 1 to 7 carbon atoms or halo-lower alkyl of 1 to 7 carbon atoms, or taken together with the nitrogen atom, are piperidino, piperazino, pyrrolidino, morpholino, imidazoline, 4-lower alkylpiperazino wherein lower alkyl is of 1-7 carbon atoms an methylpiperidino, and B is hydrogen, lower alkyl of 1 to 7 carbon atoms or lower alkanoyl of 1 to 7 carbon atoms; and R 9 is halogen, lower alkyl of 1 to 7 carbon atoms, lower alkoxy of 1 to 7 carbon atoms, amino, cyano or nitro; provided that at least one of R 3 or R 4 is a basic amino side chain or --A--O--B, or an addition salt thereof with a pharmaceutically acceptable acid.
Claim 15
Dependent Claim
255 words
In accordance with claim 11, a compound of the formula ##STR41## wherein R 3 is hydrogen, halogen, trifluoromethyl, hydrazino, lower alkyl of 1 to 7 carbon atoms, lower alkoxy of 1 to 7 carbon atoms, lower alkoxyamino of 1 to 7 carbon atoms or ##STR42## wherein A is a straight chain lower alkylene of 2-7 carbon atoms or a straight chain lower alkylene of 2 to 7 carbon atoms mono-substituted by lower alkyl of 1 to 7 carbon atoms, R 6 and R 7 , independently, are hydrogen or lower alkyl of 1 to 7 carbon atoms, or taken together with the nitrogen atom, are piperidino, piperazino, pyrrolidino, morpholino, imidazoline, 4-lower alkylpiperazino wherein lower alkyl is of 1 to 7 carbon atoms or methylpiperidino, and R 8 is hydrogen or lower alkyl of 1 to 7 carbon atoms; R 4 is hydrogen or ##STR43## wherein A is a straight chain lower alkylene of 2-7 carbon atoms or a straight chain lower alkylene of 2-7 carbon atoms mono- substituted by lower alkyl of 1 to 7 carbon atoms, R 6 and R 7 , independently, are hydrogen or lower alkyl of 1 to 7 carbon atoms, or taken together with the nitrogen atom, are piperidino, piperazino, pyrrolidino, morpholino, imidazoline, 4-lower alkylpiperazino wherein lower alkyl is of 1 to 7 carbon atoms or methylpiperidino and R 9 is nitro, halogen, or trifluoromethyl; provided that one of R 3 or R 4 is a basic amino side chain; or an addition salt thereof with a pharmaceutically acceptable acid.
Claim 16
Dependent Claim
26 words
A compound in accordance with claim 12, wherein one of R 3 or R 4 is hydrogen and the other is a basic amino side chain.
Claim 17
Dependent Claim
8 words
The compound in accordance with claim 13, 6,10-dichloro-7-(2-diethylaminoethyl)indolo[2,3-c]quinoline.
Claim 18
Dependent Claim
8 words
The compound in accordance with claim 13, 10-chloro-6-(2-diethylaminoethylamino)indolo[2,3-c]quinoline.
References Cited (Backward Citations)
US3420834A
Cited
US3326920A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-03-28 | 1980-09-27 | 1981-03-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-03-28 | 1984-09-27 | 1985-03-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-03-28 | 1988-09-27 | 1989-03-29 | $7700.00 | Window Closed / Lapsed |