US4472399A
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US
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Indolo[2',3';3,4]pyrido[2,1-b]quinazoline-5-ones, a process for the preparation thereof, and diuretic compositions and methods using them
Assignee: Chinoin Private Co Ltd
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Filing: 1981-10-02
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Granted: 1984-09-18
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Expires: 2001-10-02
Abstract
Abstract New Rutecarpine analogs are disclosed having Rutecarpine-like activity, especially diuretic activity. Also a novel process for the preparation of the Rutecarpine analogs is disclosed.
Inventors
- 👤 Jozsef Kokosi
- 👤 Istvan Hermecz
- 👤 Zoltan Meszaros
- 👤 Sandor Virag
- 👤 nee Debreczy Lelle Vasvari
- 👤 Gyorgy Szasz
- 👤 Agnes Horvath
- 👤 Tibor Breining
- 👤 Tamas Szuts
- 👤 Gyula Sebestyen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 02:15
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/12; C07D471/14
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
224 words
Process for the preparation of an indolo(2',3';3,4)pyrido(2,1-b)quinazoline-5-one of the formula (I) ##STR10## wherein R stands for hydrogen or C 1-4 alkyl, R 1 , R 2 and R 3 are the same or different and stand for hydrogen(s), halogen(s), C 1-4 alkyl, C 1-4 alkoxy, phenyl, cyano, trifuloromethyl, C 1-4 alkanoyl, nitro, carboxy, C 2-5 alkoxycarbonyl, amino, C 1-4 alkanoyl amino, phenyloxy, hydroxy, C 1-4 alkyl containing dialkylamino, carbamoyl, C 7-12 aralkoxy, carbohydrazido, alkylaminocarbonyl of 1-4 carbon atoms in the alkyl group, dialkylaminocarbonyl(s) containing 1-4 carbon atoms in the alkyl part, or optionally R 1 and R 2 together form methylenedioxy or --(CH═CH) 2 attached to two adjacent carbon atoms of the benzene ring, R 4 , R 5 and R 6 are the same or different and stand for hydrogen(s), halogen(s), C 1-4 alkyl, C 1-4 alkoxy, phenyl, cyano, C 1-4 alkanoyl, nitro, carboxy, C 1-4 alkoxycarbonyl, amino, C 1-4 alkanoyl amino, hydroxy, C 1-4 alkylamino, dialkylamino containing 1-4 carbon atoms in the alkyl part, carbamoyl, C 7-12 aralkoxy, carbohydrazido, C 1-4 alkylaminocarbonyl, dialkylaminocarbonyl group(s) containing 1-4 carbon atoms of the benzene ring, and the dotted lines represent optionally present further chemical bonds, which comprises treating a 6-phenyl-hydrazono-11H-pyrido(2,1-b)quinazoline-11-one or a pharmaceutically acceptable acid-addition salt thereof of the formula (II) ##STR11## acid and converting the thus obtained indolo(2',3';3,4)pyrido(2,1-b)-quinazoline-5-one, if desired, to an acid-addition salt.
Claim 2
Dependent Claim
224 words
Process for the preparation of an indolo(2',3';3,4)pyrido(2,1-b)quinazoline-5-one of the formula (I) ##STR10## wherein R stands for hydrogen or C 1-4 alkyl, R 1 , R 2 and R 3 are the same or different and stand for hydrogen(s), halogen(s), C 1-4 alkyl, C 1-4 alkoxy, phenyl, cyano, trifuloromethyl, C 1-4 alkanoyl, nitro, carboxy, C 2-5 alkoxycarbonyl, amino, C 1-4 alkanoyl amino, phenyloxy, hydroxy, C 1-4 alkyl containing dialkylamino, carbamoyl, C 7-12 aralkoxy, carbohydrazido, alkylaminocarbonyl of 1-4 carbon atoms in the alkyl group, dialkylaminocarbonyl(s) containing 1-4 carbon atoms in the alkyl part, or optionally R 1 and R 2 together form methylenedioxy or --(CH═CH) 2 attached to two adjacent carbon atoms of the benzene ring, R 4 , R 5 and R 6 are the same or different and stand for hydrogen(s), halogen(s), C 1-4 alkyl, C 1-4 alkoxy, phenyl, cyano, C 1-4 alkanoyl, nitro, carboxy, C 1-4 alkoxycarbonyl, amino, C 1-4 alkanoyl amino, hydroxy, C 1-4 alkylamino, dialkylamino containing 1-4 carbon atoms in the alkyl part, carbamoyl, C 7-12 aralkoxy, carbohydrazido, C 1-4 alkylaminocarbonyl, dialkylaminocarbonyl group(s) containing 1-4 carbon atoms of the benzene ring, and the dotted lines represent optionally present further chemical bonds, which comprises treating a 6-phenyl-hydrazono-11H-pyrido(2,1-b)quinazoline-11-one or a pharmaceutically acceptable acid-addition salt thereof of the formula (II) ##STR11## acid and converting the thus obtained indolo(2',3';3,4)pyrido(2,1-b)-quinazoline-5-one, if desired, to an acid-addition salt.
Claim 3
Dependent Claim
18 words
Process as claimed in claim 1 which comprises using organic, inorganic acids or Lewis acids as the acid.
Claim 4
Dependent Claim
23 words
Process as claimed in claim 2 which comprises using phosphoric acid, polyphosphoric acid, hydrochloric acid, hydrobromic acid or sulphuric acid as the acid.
Claim 5
Dependent Claim
17 words
Process as claimed in claim 2 which comprises using an alkane carboxylic acids, as the organic acid.
Claim 6
Dependent Claim
17 words
Process as claimed in claim 2 which comprises using as Lewis acid, aluminum chloride or zinc chloride.
Claim 7
Dependent Claim
19 words
Process as claimed in claim 1 which comprises using hydrochloride as acid-addition salt of the compound of formula (II).
Claim 8
Dependent Claim
28 words
Process as claimed in claim 1 which comprises heating a compound of the formula (II) or acid-addition salt thereof at a temperature ranging from 100° to 220° C.
Claim 9
Dependent Claim
33 words
Process as claimed in claim 7, which comprises heating a compound of formula (II) or hydrochloride salt thereof in the presence of polyphosphoric acid at a temperature ranging from 140° to 210° C.
Claim 10
Dependent Claim
45 words
A compound of the formula (I) ##STR12## or a pharmaceutically acceptable acid addition salt thereof wherein R is hydrogen or C 1 to C 4 alkyl; and R 1 , R 2 and R 3 are hydrogen, C 1 to C 4 alkyl, or halogen.
Claim 11
Dependent Claim
45 words
A compound of the formula (I) ##STR12## or a pharmaceutically acceptable acid addition salt thereof wherein R is hydrogen or C 1 to C 4 alkyl; and R 1 , R 2 and R 3 are hydrogen, C 1 to C 4 alkyl, or halogen.
Claim 12
Dependent Claim
14 words
5-oxo-1,2,3,4,7,8-hexahydro-5H,13H-indolo(2',3';3,4)-pyrido]2,1-b)quinazoline or a pharmaceutically acceptable acid addition salt thereof as defined in claim 9.
Claim 13
Dependent Claim
14 words
7,10-dimethyl-5-oxo-1,2,3,4,7,8-hexahydro-5H,13H-indolo(2',3';3,4)pyrido(2,1-b)quinazoline or a pharmaceutically acceptable acid addition salt thereof as defined in claim 9.
Claim 14
Dependent Claim
14 words
7-methyl-10-chloro-5-oxo-1,2,3,4,7,8-hexahydro-5H,13H-indolo(2',3';3,4)pyrido(2,1-b)quinazoline or a pharmaceutically acceptable acid addition salt thereof as defined in claim 9.
Claim 15
Dependent Claim
14 words
8-methyl-5-oxo-1,2,3,4,7,8-hexahydro-5H,13H-indolo(2',3';3,4)pyrido(2,1-b)quinazoline or a pharmaceutically acceptable acid addition salt thereof as defined in claim 9.
Claim 16
Dependent Claim
14 words
9,11-dichloro-5-oxo-1,2,3,4,7,8-hexahydro-5H,13H-indolo(2',3';3,4,)pyrido(2,1-b)quinazoline or a pharmaceutically acceptable acid addition salt thereof as defined in claim 9.
Claim 17
Dependent Claim
14 words
7-methyl-5-oxo-1,2,3,4,7,8-hexahydro-5H,13H-indolo(2',3';3,4,)pyrido(2,1-b)quinazoline or a pharmaceutically acceptable acid addition salt thereof as defined in claim 9.
Claim 18
Dependent Claim
37 words
A diuretic composition comprising as active ingredient a pharmaceutically effective amount of a compound of the formula (I) as defined in claim 9 or a pharmaceutically acceptable acid addition salt thereof along with a pharmaceutically acceptable carrier.
Claim 19
Dependent Claim
44 words
A diuretic method of treatment which comprises the step of administering to an animal subject in need of said treatment a pharmaceutically effective amount of the compound of the formula (I) as defined in claim 9 or a pharmaceutically acceptable acid addition salt thereof.
Claim 20
Dependent Claim
40 words
A compound of the formula (I) ##STR13## or a pharmaceutically acceptable acid addition salt thereof wherein R is hydrogen or C 1 to C 4 alkyl; and R 3 is C 1 to C 4 alkyl, halogen, cyano or phenoxy.
Claim 21
Dependent Claim
40 words
A compound of the formula (I) ##STR13## or a pharmaceutically acceptable acid addition salt thereof wherein R is hydrogen or C 1 to C 4 alkyl; and R 3 is C 1 to C 4 alkyl, halogen, cyano or phenoxy.
Claim 22
Dependent Claim
14 words
10-methyl-7,8-dihydro-5H,13H-indolo(2',3';3,4,)-pyrido(2,1-b)quinazoline-5-one or a pharmaceutically acceptable acid addition salt thereof as defined in claim 18.
Claim 23
Dependent Claim
14 words
10-chloro-7,8-dihydro-5H,13H-indolo(2',3';3,4)-pyrido(2,1-b)quinazoline-5-one or a pharmaceutically acceptable acid addition salt thereof as defined in claim 18.
Claim 24
Dependent Claim
14 words
10-fluoro-7,8-dihydro-5H,13H-indolo(2',3';3,4,)-pyrido(2,1-b)quinazoline-5-one or a pharmaceutically acceptable acid addition salt thereof as defined in claim 18.
Claim 25
Dependent Claim
14 words
10-bromo-7,8-dihydro-5H,13H-indolo(2',3';3,4,)-pyrido(2,1-b)quinazoline-5-one or a pharmaceutically acceptable acid addition salt thereof as defined in claim 18.
Claim 26
Dependent Claim
14 words
10-cyano-7,8-dihydro-5H,13H-indolo(2',3';3,4)-pyrido(2,1-b)quinazoline-5-one or a pharmaceutically acceptable acid addition salt thereof as defined in claim 18.
Claim 27
Dependent Claim
14 words
10-phenyloxy-7,8-dihydro-5H,13H-indolo(2',3';3,4,)-pyrido(2,1-b)quinazoline-5-one or a pharmaceutically acceptable acid addition salt thereof as defined in claim 18.
Claim 28
Dependent Claim
37 words
A diuretic composition comprising as active ingredient a pharmaceutically effective amount of a compound of the formula (I) as defined in claim 18 or a pharmaceutically acceptable acid addition salt thereof along with a pharmaceutically acceptable carrier.
Claim 29
Dependent Claim
44 words
A diuretic method of treatment which comprises the step of administering to an animal subject in need of said treatment a pharmaceutically effective amount of the compound of the formula (I) as defined in claim 18 or a pharmaceutically acceptable acid addition salt thereof.
Claim 30
Dependent Claim
36 words
A compound of the Formula I ##STR14## or a pharmaceutically acceptable acid addition salt thereof wherein R is hydrogen or C 1 to C 4 alkyl and R 3 is C 1 to C 4 alkyl.
Claim 31
Dependent Claim
36 words
A compound of the Formula I ##STR14## or a pharmaceutically acceptable acid addition salt thereof wherein R is hydrogen or C 1 to C 4 alkyl and R 3 is C 1 to C 4 alkyl.
Claim 32
Dependent Claim
27 words
The compound of the Formula I defined in claim 27 wherein R 3 is a substituent in the 10-position of the rutecarpine nucleus, and R is hydrogen.
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) | 1987-09-18 | 1988-03-19 | 1988-09-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-09-18 | 1992-03-19 | 1992-09-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-09-18 | 1996-03-19 | 1996-09-18 | $7700.00 | Window Closed / Lapsed |