Patent US2223415A successfully refreshed from Google Patents.
US3966938A
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Treatment of thrombosis and the inhibition of blood platelet aggregation
Assignee: Sandoz AG
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Filing: 1975-05-08
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Granted: 1976-06-29
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Expires: 1995-05-08
Abstract
Abstract The invention concerns new 4a,10b-cis-substituted benzo-naphthyridines of the formula: ##SPC1## Wherein R 1 is hydrogen, alkyl, alkoxy, alkylthio, fluorine, chlorine, bromine, nitro, trifluoromethyl, amino or acylamino, R 2 is hydrogen, chlorine, alkyl or alkoxy, and R 3 and R 4 are both hydrogen or both methoxy, or R 3 and R 4 together are methylenedioxy. A process for the production thereof and intermediates therefor are also described. The compounds inhibit blood platelet aggregation.
Inventors
- 👤 Hans Ott
- 👤 Rudolf Suess
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 00:08
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/56; C07D211/58
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
226 words
A method of treating thrombosis in animals, which comprises orally administering to an animal in need of such treatment a therapeutically effective amount of a compound of formula: ##SPC16## wherein R 1 is hydrogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms or alkylthio of 1 to 3 carbon atoms, fluorine, bromine, chlorine, nitro, trifluoromethyl, amino or --NH--CO--R, wherein --CO--R is alkanoyl of 1 to 18 carbon atoms, benzoyl, benzoyl wherein the benzene ring is substituted by one X and one Y, X being lower alkyl of 1 to 4 carbon atoms, lower alkoxy of 1 to 4 carbon atoms, fluorine, chlorine, or bromine, and Y being hydrogen, lower alkyl of 1 to 4 carbon atoms, lower alkoxy of 1 to 4 carbon atoms, or chlorine, phenylalkenoyl wherein the akylene section has 1 to 3 carbon atoms, cinnamoyl, phenylalkenoyl as defined above or cinnamoyl which are substituted in the benzene ring by one X and one Y which are as defined above, or A-CO-, A being thienyl, furyl, pyrrolyl, or pyridyl, R 2 is hydrogen, chlorine, alkyl of 1 to 3 carbon atoms or alkoxy of 1 to 3 carbon atoms, and R 3 and R 4 are both hydrogen or both methoxy, or R 3 and R 4 together are methylenedioxy, or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Independent Claim
226 words
A method of treating thrombosis in animals, which comprises orally administering to an animal in need of such treatment a therapeutically effective amount of a compound of formula: ##SPC16## wherein R 1 is hydrogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms or alkylthio of 1 to 3 carbon atoms, fluorine, bromine, chlorine, nitro, trifluoromethyl, amino or --NH--CO--R, wherein --CO--R is alkanoyl of 1 to 18 carbon atoms, benzoyl, benzoyl wherein the benzene ring is substituted by one X and one Y, X being lower alkyl of 1 to 4 carbon atoms, lower alkoxy of 1 to 4 carbon atoms, fluorine, chlorine, or bromine, and Y being hydrogen, lower alkyl of 1 to 4 carbon atoms, lower alkoxy of 1 to 4 carbon atoms, or chlorine, phenylalkenoyl wherein the akylene section has 1 to 3 carbon atoms, cinnamoyl, phenylalkenoyl as defined above or cinnamoyl which are substituted in the benzene ring by one X and one Y which are as defined above, or A-CO-, A being thienyl, furyl, pyrrolyl, or pyridyl, R 2 is hydrogen, chlorine, alkyl of 1 to 3 carbon atoms or alkoxy of 1 to 3 carbon atoms, and R 3 and R 4 are both hydrogen or both methoxy, or R 3 and R 4 together are methylenedioxy, or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
85 words
The method of claim 1, wherein the compound is of the formula: ##SPC17## wherein R is hydrogen, alkyl of 1 to 17 carbon atoms, thienyl, furyl, pyrrolyl, pyridyl or ##SPC18## wherein A is a direct bond, alkylene of 1 to 3 carbon atoms or vinylene, X is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, fluorine, chlorine or bromine, and Y is hydrogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms.
Claim 4
Dependent Claim
89 words
The method of claim 1, wherein in the compound R 1 is hydrogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms or alkylthio of 1 to 3 carbon atoms, fluorine, bromine, chlorine, nitro, trifluoromethyl, amino or amido of 2 to 4 carbon atoms, R 2 is hydrogen, chlorine, alkyl of 1 to 3 carbon atoms or alkoxy of 1 to 3 carbon atoms, and R 3 and R 4 are both hydrogen or methoxy, or R 3 and R 4 together are methylenedioxy.
Claim 5
Dependent Claim
10 words
The method of claim 1, wherein the compound is cis-6-(4-acetamidophenyl)-1,2,3,4,4a,10b-hexyhydro-8,9-dimethoxy-2-methyl-benzo[c][1,6]naphthyridine.
Claim 6
Dependent Claim
10 words
The method of claim 1, wherein the compound is cis-1,2,3,4,4a,10b-hexahydro-8,9-dimethoxy-2-methyl-6-phenyl-benzo[c][1,6]naphthyridine.
Claim 7
Dependent Claim
25 words
The method of claim 1, wherein the compound is administered at a daily dose of from about 0.1 to about 10 mg/kg animal body weight.
Claim 8
Dependent Claim
23 words
The method of claim 6, wherein the compound is administered at a daily dose of from about 10 mg to about 400 mg.
Claim 9
Dependent Claim
26 words
The method of claim 7, wherein the compound is orally administered in unit dosage form, containing from about 3 to about 200 mg of the compound.
Claim 10
Dependent Claim
10 words
The method of claim 8, wherein the compound is cis-1,2,3,4,4a,10b-hexahydro-8,9-dimethoxy-2-methyl-6-phenyl-benzo[c][1,6]naphthyridine.
Claim 11
Dependent Claim
10 words
The method of claim 8, wherein the compound is cis-6-(4-acetamidophenyl)-1,2,3,4,4a,10b-hexahydro-8,9-dimethoxy-2-methyl-benzo[c][1,6]naphthyridine.
Claim 12
Independent Claim
228 words
A method of inhibiting blood platelet aggregation in animals which comprises orally administering to an animal in need of such treatment a therapeutically effective amount of a compound of formula: ##SPC19## wherein R 1 is hydrogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms or alkylthio of 1 to 3 carbon atoms, fluorine, bromine, chlorine, nitro, trifluoromethyl, amino or --NH--CO--R, wherein --CO--R is alkanoyl of 1 to 18 carbon atoms, benzoyl, benzoyl wherein the benzene ring is substituted by one X and one Y, X being lower alkyl of 1 to 4 carbon atoms, lower alkoxy of 1 to 4 carbon atoms, fluorine, chlorine, or bromine, and Y being hydrogen, lower alkyl of 1 to 4 carbon atoms, lower alkoxy of 1 to 4 carbon atoms, or chlorine, phenylalkenoyl, wherein the alkylene section has 1 to 3 carbon atoms, cinnamoyl, phenylalkenoyl as defined above or cinnamoyl which are substituted in the benzene ring by one X and one Y which are as defined above, or A-CO-, A being thienyl, furyl, pyrrolyl, or pyridyl, R 2 is hydrogen, chlorine, alkyl of 1 to 3 carbon atoms, or alkoxy of 1 to 3 carbon atoms, and R 3 and R 4 are both hydrogen or both methoxy, or R 3 and R 4 together are methylenedioxy, or a pharmaceutically acceptable acid addition salt thereof.
Claim 13
Independent Claim
228 words
A method of inhibiting blood platelet aggregation in animals which comprises orally administering to an animal in need of such treatment a therapeutically effective amount of a compound of formula: ##SPC19## wherein R 1 is hydrogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms or alkylthio of 1 to 3 carbon atoms, fluorine, bromine, chlorine, nitro, trifluoromethyl, amino or --NH--CO--R, wherein --CO--R is alkanoyl of 1 to 18 carbon atoms, benzoyl, benzoyl wherein the benzene ring is substituted by one X and one Y, X being lower alkyl of 1 to 4 carbon atoms, lower alkoxy of 1 to 4 carbon atoms, fluorine, chlorine, or bromine, and Y being hydrogen, lower alkyl of 1 to 4 carbon atoms, lower alkoxy of 1 to 4 carbon atoms, or chlorine, phenylalkenoyl, wherein the alkylene section has 1 to 3 carbon atoms, cinnamoyl, phenylalkenoyl as defined above or cinnamoyl which are substituted in the benzene ring by one X and one Y which are as defined above, or A-CO-, A being thienyl, furyl, pyrrolyl, or pyridyl, R 2 is hydrogen, chlorine, alkyl of 1 to 3 carbon atoms, or alkoxy of 1 to 3 carbon atoms, and R 3 and R 4 are both hydrogen or both methoxy, or R 3 and R 4 together are methylenedioxy, or a pharmaceutically acceptable acid addition salt thereof.
Claim 14
Dependent Claim
85 words
The method of claim 11, wherein the compound is of the formula: ##SPC20## wherein R is hydrogen, alkyl of 1 to 17 carbon atoms, thienyl, furyl, pyrrolyl, pyridyl or ##SPC21## wherein A is a direct bond, alkylene of 1 to 3 carbon atoms or vinylene, X is hydrogen, alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms, fluorine, chlorine or bromine, and Y is hydrogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms.
Claim 15
Dependent Claim
89 words
The method of claim 11, wherein in the compound R 1 is hydrogen, alkyl of 1 to 3 carbon atoms, alkoxy of 1 to 3 carbon atoms or alkylthio of 1 to 3 carbon atoms, fluorine, bromine, chlorine, nitro, trifluoromethyl, amino or amido of 2 to 4 carbon atoms, R 2 is hydrogen, chlorine, alkyl of 1 to 3 carbon atoms or alkoxy of 1 to 3 carbon atoms, and R 3 and R 4 are both hydrogen or methoxy, or R 3 and R 4 together are methylenedioxy.
Claim 16
Dependent Claim
10 words
The method of claim 11, wherein the compound is cis-6-(4-acetamidophenyl)-1,2,3,4,4a,10b-hexahydro-8,9-dimethoxy-2-methyl-benzo[c][1,6]naphthyridine.
Claim 17
Dependent Claim
10 words
The method of claim 11, wherein the compound is cis-1,2,3,4,4a,10b-hexahydro-8,9-dimethoxy-2-methyl-6-phenyl-benzo[c][1,6]naphthyridine.
Claim 18
Dependent Claim
25 words
The method of claim 11, wherein the compound is administered at a daily dose of from about 0.1 to about 10 mg/kg animal body weight.
Claim 19
Dependent Claim
23 words
The method of claim 16, wherein the compound is administered at a daily dose of from about 10 mg to about 400 mg.
Claim 20
Dependent Claim
26 words
The method of claim 17, wherein the compound is orally administered in unit dosage form, containing from about 3 to about 200 mg of the compound.
Claim 21
Independent Claim
10 words
The method of claims 18, wherein the compound is cis-1,2,3,4,4a,10b-hexahydro-8,9-dimethoxy-2-methyl-6-phenyl-benzo[c][1,6]naphthyridine.
Claim 22
Dependent Claim
10 words
The method of claim 18, wherein the compound is cis-6-(4-acetamidophenyl)-1,2,3,4,4a,10b-hexahydro-8,9-dimethoxy-2-methyl-benzo[c][1,6]naphthyridine.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1979-06-29 | 1979-12-29 | 1980-06-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1983-06-29 | 1983-12-29 | 1984-06-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1987-06-29 | 1987-12-29 | 1988-06-29 | $7700.00 | Window Closed / Lapsed |