US4266060A
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US
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Dipyrido [4,3-b] [3,4-f] indoles and process for obtaining them
Assignee: Bpifrance Financement SA
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Filing: 1978-04-13
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Granted: 1981-05-05
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Expires: 1998-04-13
Abstract
Abstract The invention relates to compounds of formula: <IMAGE> wherein R'1=H, OH or an alkyl group, preferably a lower alkyl group, alkylthio or alkoxy, an halogen or an amino group, R'2=H or a lower alkyl group.
Inventors
- 👤 Emile Bisagni
- 👤 Claire Ducrocq
- 👤 Christian Rivalle
- 👤 Pierre Tambourin
- 👤 Francoise Wendling
- 👤 Jean-Claude Chermann
- 👤 Luc Montagnier
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 21:59
CPC Classifications
C; C07; C07D; C07D487/00; C07D487/02; C07D487/04; A; A61; A61P; A61P31/00; A61P31/04; A61P35/00; A61P35/02; C07C; C07C205/00; C07C205/44; C07C205/49; C07C205/56; C07C247/00; C07D217/00; C07D217/22; C07D217/24; C07D487/12; C07D487/14
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
70 words
A dipyrido [ 4,3-b] [3,4-f] indole of the formula ##STR33## in which: R' 1 is hydrogen, hydroxy, lower alkyl, halogen or an amino group of the formula ##STR34## wherein n is an integer from 1 to 3, R' 6 is hydrogen or lower alkyl, R' 4 and R' 5 each independently is hydrogen or lower alkyl, and R' 2 is hydrogen or lower alkyl, or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
70 words
A dipyrido [ 4,3-b] [3,4-f] indole of the formula ##STR33## in which: R' 1 is hydrogen, hydroxy, lower alkyl, halogen or an amino group of the formula ##STR34## wherein n is an integer from 1 to 3, R' 6 is hydrogen or lower alkyl, R' 4 and R' 5 each independently is hydrogen or lower alkyl, and R' 2 is hydrogen or lower alkyl, or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
18 words
A compound according to claim 1, wherein R' 2 is methyl and R' 1 is hydrogen or hydroxy.
Claim 4
Dependent Claim
16 words
A compound according to claim 1, wherein R' 2 is hydrogen and R' 1 is chloro.
Claim 5
Dependent Claim
24 words
A compound according to claim 1, wherein R' 2 is methyl and R' 1 is halogen or an amino group of the formula ##STR35##
Claim 6
Dependent Claim
25 words
A compound according to claim 1, wherein R' 2 is hydrogen, and R' 1 is hydroxy, halogen or an amino group of the formula ##STR36##
Claim 7
Dependent Claim
26 words
A compound according to claim 5, wherein R' 6 is hydrogen or methyl and R' 4 and R' 5 each independently is hydrogen methyl or ethyl.
Claim 8
Dependent Claim
80 words
A compound according to claim 1, selected from the group consisting of 5,11-dimethyl dipyrido [4,3-b] [;3,4-f] indole; 2,5,9,11-tetramethyl dipyrido [4,3-b] [3,4-f] indolinium diacetate; 5,11-dimethyl dipyrido [4,3-b] [3,4-f]indole acetate; 5,11-dimethyl dipyrido [4,3-b] [3,4-f] indole dihydrochloride; 1,2-dihydro-oxo-5-methyl dipyrido [4,3-b] [3,4-f] indole; 1-chloro-5-methyl dipyrido [4,3-b] [3,4-f] indole; 1[(γ-diethylaminopropyl) amino]5-methyl dipyrido [4,3-b 3,4-f] indole; 1-[(γ-dimethylaminopropyl) amino]5-methyl dipyrido [4,3-b ] [3,4-f] indole; 1[(β-dimethylaminoethyl) amino]-5-methyl dipyrido [4,3-b] [3,4] indole; -1[(α-methyl-δ-diethylamino-butyl) amino]-5-methyl dipyrido [4,3-b] [3,4-f] indole; -1-[(γ-amino-propyl)amino]-5-methyl dipyrido [4,3-b] [3,4-f] indole; and 1,2-dihydro-1-oxo-5,11-dimethyl dipyrido [4,3-b] [3,4-f] indole.
Claim 9
Dependent Claim
79 words
A process for preparing a compound according to claim 1, comprising the steps of: (1) reacting a 6-amino-isoquinoline with 3-nitro-4-chloropyridine to form the corresponding 6-[4'-(3'-nitropyridyl) amino] isoquinoline; (2) hydrogenating said isoquinoline thus obtained into the corresponding amino compound; (3) reacting the corresponding amino compound with sodium nitrite to form the corresponding triazolopyridine; (4) converting the triazolopyridine thus obtained into the corresponding dipyrido [4,3-b] [3,4-f] indole, and (5) optionally forming the pharmaceutically acceptable salt of the dipyrido indole thus obtained.
Claim 10
Dependent Claim
21 words
A process according to claim 8, wherein the hydrogenation of step (2) is effected in the presence of a hydrogenation catalyst.
Claim 11
Dependent Claim
20 words
A process according to claim 8, wherein step (4) is effected in the presence of an inert high melting material.
Claim 12
Dependent Claim
76 words
A process according to claim 8, wherein the 6-amino-isoquinoline is one of the tautomers ##STR37## and is obtained by converting the amino group of a 2-methyl-3-amino-benzonitrile into an acetylamino group, converting the cyano group of the 2-methyl-3-acetylamino-benzonitrile into the aldehyde group, condensing the latter with malonic acid to form an acid of the formula ##STR38## forming the azide of the acid cyclizing to form the corresponding isoquinolone, and eliminating the acetyl group from the amino group.
Claim 13
Dependent Claim
67 words
A process according to claim 8, wherein the 6-amino- isoquinoline is one of the tautomers ##STR39## and is obtained by converting a 2-methyl-3-nitro-aniline into a (2-methyl-3-nitro-phenyl) chloropropionic acid, converting the latter compound into a 2-methyl-3-nitro-cinnamic acid by elimination of HCl, converting the nitro group into the amino group and thenthe acetylamino group, cyclizing to form the corresponding isoquinolone, and eliminating the acetyl group from the amino group.
Claim 14
Dependent Claim
73 words
A process according to claim 8, wherein the 6-aminoisoquinoline is one of the tautomers ##STR40## and is obtained by converting the chloromethyl group of ##STR41## into an aldehyde group, condensing this aldehyde group with malonic acid to form the corresponding cinnamic acid, reducing the nitro group into an amino group, coverting the amino group into an acetylamino group, cyclizing to form the corresponding isoquinolone, and eliminating the acetyl group from the amino group.
Claim 15
Dependent Claim
34 words
A process according to claim 8, wherein R, 1 is ##STR42## comprising the further steps of chlorinating the 1,2-dihydro-1-oxo- 5-methyl-dipyrido [4,3-b] [3,4-f] indole, and reacting the chlorinated compound so obtained with the appropriate amine.
Claim 16
Dependent Claim
11 words
A compound according to claim 1, wherein R' 2 is hydrogen.
Claim 17
Dependent Claim
11 words
A compound according to claim 1, wherein R' 2 is methyl.
References Cited (Backward Citations)
US4045565A
Cited
US3933827A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-05-04 | 1984-11-03 | 1985-05-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-05-04 | 1988-11-03 | 1989-05-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-05-04 | 1992-11-03 | 1993-05-05 | $7700.00 | Window Closed / Lapsed |