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US4009273A
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Substituted 10,11-dihydro-5,10-imino-[5H] dibenzo (a,d)-cycloheptene
Assignee: Sanofi Aventis France
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Filing: 1975-04-14
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Granted: 1977-02-22
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Expires: 1995-04-14
Abstract
Abstract Racemates and optically active isomers of a compound selected from the group consisting of a compound of the formula ##STR1## wherein R is selected from the group consisting of hydrogen, lower alkyl optionally substituted with a member of the group consisting of hydroxy and halogen, lower alkenyl, lower alkynyl, --(CH 2 ) n -- COCH 3 where n is 0 or 1, ##STR2## wherein X is selected from the group consisting of lower alkyl and optionally substituted phenyl, aralkyl or 7 to 8 carbon atoms, acyl of an organic carboxylic acid of 1 to 6 carbon atoms optionally substituted with ##STR3## where m is an integer from 0 to 6 and X 1 is selected from the group consisting of hydrogen and lower alkyl, ##STR4## where p is an integer from 1 to 6 and X 1 is as before and ##STR5## wherein X 2 is lower alkyl and R 1 and R 2 are individually selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, trifluoromethyl and dilower alkylamino and the non-toxic, pharmaceutically acceptable acid addition and quaternary ammonium salts thereof which have a stimulating effect on the central nervous system while possessing at the same time anticonvulsant activity and their preparation.
Inventors
- 👤 Lucien Nedelec
- 👤 Daniel Frechet
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 03:45
CPC Classifications
C; C07; C07D; C07D451/00; C07D451/02; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6561
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
163 words
A compound selected from the group consisting of racemates and optically active isomers of a compound of the formula ##STR39## wherein R is selected from the group consisting of --(CH 2 ) n --COCH 3 where n is O or 1, ##STR40## wherein X is selected from the group consisting of lower alkyl, phenyl, nitro-phenyl, phenylalkyl of 7 to 8 carbon atoms, acyl of a saturated aliphatic mono carboxylic acid of 1 to 6 carbon atoms optionally substituted with ##STR41## where m is an integer from O to 6 and X 1 is selected from the group consisting of hydrogen and lower alkyl, ##STR42## where p is an integer from 1 to 6 and X 1 is as before, ##STR43## wherein X 2 is lower alkyl, and R 1 and R 2 are individually selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, CF 3 - and diloweralkylamino and the non-toxic, pharmaceutically acceptable acid addition and quaternary ammonium salts thereof.
Claim 2
Dependent Claim
163 words
A compound selected from the group consisting of racemates and optically active isomers of a compound of the formula ##STR39## wherein R is selected from the group consisting of --(CH 2 ) n --COCH 3 where n is O or 1, ##STR40## wherein X is selected from the group consisting of lower alkyl, phenyl, nitro-phenyl, phenylalkyl of 7 to 8 carbon atoms, acyl of a saturated aliphatic mono carboxylic acid of 1 to 6 carbon atoms optionally substituted with ##STR41## where m is an integer from O to 6 and X 1 is selected from the group consisting of hydrogen and lower alkyl, ##STR42## where p is an integer from 1 to 6 and X 1 is as before, ##STR43## wherein X 2 is lower alkyl, and R 1 and R 2 are individually selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, CF 3 - and diloweralkylamino and the non-toxic, pharmaceutically acceptable acid addition and quaternary ammonium salts thereof.
Claim 3
Dependent Claim
20 words
A compound of claim 1 wherein R is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl and hydroxyethyl.
Claim 4
Dependent Claim
21 words
A compound of claim 1 selected from the group consisting of 12-(3'-dimethylaminopropyl)-10,11-dihydro-5,10-imino-[5H]-dibenzo (a,d)-cycloheptene and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 5
Dependent Claim
21 words
A compound of claim 1 selected from the group consisting of 12-dimethylaminoacetyl-10,11-dihydro-5,10-imino-[5H]-dibenzo (a,d)-cycloheptene and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 6
Dependent Claim
21 words
A compound of claim 1 selected from the group consisting of 12-methyl-10,11-dihydro-5,10-imino-[5H]-dibenzo (a,d)-cycloheptene and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 7
Dependent Claim
21 words
A compound of claim 1 selected from the group consisting of 12-(2'-methylaminoethyl)-10,11-dihydro-5,10-imino-[5H]-dibenzo (a,d)-cycloheptene and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 8
Dependent Claim
21 words
A compound of claim 1 selected from the group consisting of 12-(2'-dimethylaminoethyl)-10,11-dihydro-5,10-imino-[5H]-dibenzo (a,d)-cycloheptene and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 9
Dependent Claim
21 words
A compound of claim 1 selected from the group consisting of 12-(2'-aminoethyl)-10,11-dihydro-5,10-imino-[5H]-dibenzo (a,d)-cycloheptene and its non-toxic, pharmaceutically acceptable acid addition salts.
Claim 10
Dependent Claim
194 words
A composition for stimulating the central nervous system comprising an amount sufficient to stimulate the central nervous system of a compound selected from the group consisting of a compound of the formula ##STR44## wherein R is selected from the group consisting of hydrogen, lower alkyl optionally substituted with hydroxy or halogen, lower alkenyl, lower alkynyl, -(CH 2 ) n COCH 3 where n is O or 1, ##STR45## wherein X is selected from the group consisting of lower alkyl, phenyl, nitro-phenyl, phenylalkyl of 7 to 8 carbon atoms, acyl of a saturated aliphatic mono carboxylic acid of 1 to 6 carbon atoms optionally substituted with ##STR46## where m is an integer from O to 6 and X 1 is selected from the group consisting of hydrogen and lower alkyl, ##STR47## where p is an integer from 1 to 6 and X 1 is as before, ##STR48## wherein X 2 is lower alkyl, and R 1 and R 2 are individually selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, CF 3 - and diloweralkylamino and the non-toxic, pharmaceutically acceptable acid addition and quaternary ammonium salts thereof and an inert pharmaceutical carrier.
Claim 11
Dependent Claim
194 words
A composition for stimulating the central nervous system comprising an amount sufficient to stimulate the central nervous system of a compound selected from the group consisting of a compound of the formula ##STR44## wherein R is selected from the group consisting of hydrogen, lower alkyl optionally substituted with hydroxy or halogen, lower alkenyl, lower alkynyl, -(CH 2 ) n COCH 3 where n is O or 1, ##STR45## wherein X is selected from the group consisting of lower alkyl, phenyl, nitro-phenyl, phenylalkyl of 7 to 8 carbon atoms, acyl of a saturated aliphatic mono carboxylic acid of 1 to 6 carbon atoms optionally substituted with ##STR46## where m is an integer from O to 6 and X 1 is selected from the group consisting of hydrogen and lower alkyl, ##STR47## where p is an integer from 1 to 6 and X 1 is as before, ##STR48## wherein X 2 is lower alkyl, and R 1 and R 2 are individually selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, CF 3 - and diloweralkylamino and the non-toxic, pharmaceutically acceptable acid addition and quaternary ammonium salts thereof and an inert pharmaceutical carrier.
Claim 12
Independent Claim
194 words
A method of stimulating the central nervous system of warm-blooded animals comprising administering to a warm-blooded animal a central nervous system stimulating amount of a compound selected from the group consisting of a compound of the formula ##STR49## wherein R is selected from the group consisting of hydrogen, lower alkyl optionally substituted with hydroxy or halogen, lower alkenyl, lower alkynyl, -(CH 2 ) n --COCH 3 where n is O or 1, ##STR50## wherein X is selected from the group consisting of lower alkyl, phenyl, nitro-phenyl, phenylalkyl of 7 to 8 carbon atoms, acyl of a saturated aliphatic mono carboxylic acid of 1 to 6 carbon atoms optionally substituted with ##STR51## where m is an integer from 0 to 6 and X 1 is selected from the group consisting of hydrogen and lower alkyl, ##STR52## where p is an integer from 1 to 6 and X 1 is as before, ##STR53## wherein X 2 is lower alkyl, and R 1 and R 2 are individually selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, CF 3 - and diloweralkylamino and the non-toxic, pharmaceutically acceptable acid addition and quaternary ammonium salts thereof.
Claim 13
Independent Claim
194 words
A method of stimulating the central nervous system of warm-blooded animals comprising administering to a warm-blooded animal a central nervous system stimulating amount of a compound selected from the group consisting of a compound of the formula ##STR49## wherein R is selected from the group consisting of hydrogen, lower alkyl optionally substituted with hydroxy or halogen, lower alkenyl, lower alkynyl, -(CH 2 ) n --COCH 3 where n is O or 1, ##STR50## wherein X is selected from the group consisting of lower alkyl, phenyl, nitro-phenyl, phenylalkyl of 7 to 8 carbon atoms, acyl of a saturated aliphatic mono carboxylic acid of 1 to 6 carbon atoms optionally substituted with ##STR51## where m is an integer from 0 to 6 and X 1 is selected from the group consisting of hydrogen and lower alkyl, ##STR52## where p is an integer from 1 to 6 and X 1 is as before, ##STR53## wherein X 2 is lower alkyl, and R 1 and R 2 are individually selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, CF 3 - and diloweralkylamino and the non-toxic, pharmaceutically acceptable acid addition and quaternary ammonium salts thereof.
Claim 14
Independent Claim
194 words
A method of treating the symptoms of Parkinson disease comprising administering to one suffering Parkinson disease an amount effective to relieve the said symptoms of a compound selected from the group consisting of a compound of the formula ##STR54## wherein R is selected from the group consisting of hydrogen, lower alkyl optionally substituted with hydroxy or halogen, lower alkenyl, lower alkynyl, -(CH 2 ) n --COCH 3 where n is O or 1, ##STR55## wherein X is selected from the group consisting of lower alkyl, phenyl, nitro-phenyl, phenylalkyl of 7 to 8 carbon atoms, acyl of a saturated aliphatic mono carboxylic acid of 1 to 6 carbon atoms optionally substituted with ##STR56## wherein m is an integer from 0 to 6 and X 1 is selected from the group consisting of hydrogen and lower alkyl, ##STR57## where p is an integer from 1 to 6 X 1 is as before, ##STR58## wherein X 2 is lower alkyl, and R 1 and R 2 are individually selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, CF 3 - and diloweralkylamino and the non-toxic, pharmaceutically acceptable acid addition and quaternary ammonium salts thereof.
Claim 15
Independent Claim
194 words
A method of treating the symptoms of Parkinson disease comprising administering to one suffering Parkinson disease an amount effective to relieve the said symptoms of a compound selected from the group consisting of a compound of the formula ##STR54## wherein R is selected from the group consisting of hydrogen, lower alkyl optionally substituted with hydroxy or halogen, lower alkenyl, lower alkynyl, -(CH 2 ) n --COCH 3 where n is O or 1, ##STR55## wherein X is selected from the group consisting of lower alkyl, phenyl, nitro-phenyl, phenylalkyl of 7 to 8 carbon atoms, acyl of a saturated aliphatic mono carboxylic acid of 1 to 6 carbon atoms optionally substituted with ##STR56## wherein m is an integer from 0 to 6 and X 1 is selected from the group consisting of hydrogen and lower alkyl, ##STR57## where p is an integer from 1 to 6 X 1 is as before, ##STR58## wherein X 2 is lower alkyl, and R 1 and R 2 are individually selected from the group consisting of hydrogen, halogen, lower alkyl, lower alkoxy, CF 3 - and diloweralkylamino and the non-toxic, pharmaceutically acceptable acid addition and quaternary ammonium salts thereof.
Claim 16
Dependent Claim
20 words
The method of claim 10 wherein R is selected from the group consisting of hydrogen, methyl, ethyl, n-propyl and hydroxyethyl.
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) | 1980-02-22 | 1980-08-23 | 1981-02-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-02-22 | 1984-08-23 | 1985-02-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-02-22 | 1988-08-23 | 1989-02-22 | $7700.00 | Window Closed / Lapsed |