US4088772A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Methanodibenzocycloheptapyrroles
Assignee: EIDP Inc
•
Filing: 1976-03-03
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Granted: 1978-05-09
•
Expires: 1996-03-03
Abstract
Abstract Methanodibenzocycloheptapyrroles, such as 2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a, 8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole, useful as tranquilizers and analgesics.
Inventors
- 👤 Engelbert Ciganek
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 04:56
CPC Classifications
C; C07; C07D; C07D209/00; C07D209/56; C07D209/58; C07D209/70; C07C; C07C2603/00; C07C2603/02; C07C2603/04; C07C2603/22; C07C2603/24
Claims Analysis
Total Claims: 45
Claim 1
Independent Claim
212 words
A compound of the formula: ##STR27## where R 1 and R 2 , the same or different = hydrogen, lower alkyl, lower alkoxy, hydroxyl, fluorine, chlorine, bromine, 2,2,2-trifluroethyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulfamyl, lower alkylcarbonyl, cycloalkylcarbonyl of 4- 7-carbons, nitro, amino, acetamido, formyl, cyano, azido, fluoromethyl, difluoromethyl, formyloxime, acetyloxime, ##STR28## where R 6 is hydrogen, lower alkyl, or alkenyl of 3-4 carbons; provided, that only one of R 1 and R 2 is nitro; R = hydrogen, alkyl of 1-10 carbons, alkenyl of 3-7 carbons attached by a saturated carbon to N, cycloalkyl of 3-5 carbons, propargyl, α-furylmethyl, α-tetrahydrofurylmethyl, α-thienylmethyl; and --(CH 2 ) n CN, --(CH 2 ) n COOH, --(CH 2 ) q OR 3 , --(CH 2 ) n COO (lower alkyl), and --(CH(R 4 )(CH 2 ) p R 5 of up to 14 carbons, where n = 1-6; p = 0-5; q = 2-6; R 3 = lower alkyl, phenyl, or lower alkylphenyl; R 4 = hydrogen or n-lower alkyl; R 5 = a hydrocarbyl group containing at least one ring of 3-9 carbons attached to alkylene by a ring carbon; provided, when p = O, the carbon attached to --CH(R 4 )-- is not a quaternary carbon; and tertiary amine oxides when R is other than hydrogen.
Claim 2
Dependent Claim
212 words
A compound of the formula: ##STR27## where R 1 and R 2 , the same or different = hydrogen, lower alkyl, lower alkoxy, hydroxyl, fluorine, chlorine, bromine, 2,2,2-trifluroethyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulfamyl, lower alkylcarbonyl, cycloalkylcarbonyl of 4- 7-carbons, nitro, amino, acetamido, formyl, cyano, azido, fluoromethyl, difluoromethyl, formyloxime, acetyloxime, ##STR28## where R 6 is hydrogen, lower alkyl, or alkenyl of 3-4 carbons; provided, that only one of R 1 and R 2 is nitro; R = hydrogen, alkyl of 1-10 carbons, alkenyl of 3-7 carbons attached by a saturated carbon to N, cycloalkyl of 3-5 carbons, propargyl, α-furylmethyl, α-tetrahydrofurylmethyl, α-thienylmethyl; and --(CH 2 ) n CN, --(CH 2 ) n COOH, --(CH 2 ) q OR 3 , --(CH 2 ) n COO (lower alkyl), and --(CH(R 4 )(CH 2 ) p R 5 of up to 14 carbons, where n = 1-6; p = 0-5; q = 2-6; R 3 = lower alkyl, phenyl, or lower alkylphenyl; R 4 = hydrogen or n-lower alkyl; R 5 = a hydrocarbyl group containing at least one ring of 3-9 carbons attached to alkylene by a ring carbon; provided, when p = O, the carbon attached to --CH(R 4 )-- is not a quaternary carbon; and tertiary amine oxides when R is other than hydrogen.
Claim 3
Dependent Claim
9 words
The compound of claim 1 where R is hydrogen.
Claim 4
Dependent Claim
211 words
A compound of the formula: ##STR29## where R 1 and R 2 , the same or diffferent = hydrogen, lower alkyl, lower alkoxy, hydroxyl, fluorine, chlorine, bromine, 2,2,2-trifluroethyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulfamyl, lower alkylcarbonyl, cycloalkylcarbonyl of 4-7 carbons, nitro, amino, acetamido, formyl, cyano, azido, fluoromethyl, difluoromethyl, formyloxime, acetyloxime, ##STR30## where R 6 is hydrogen, lower alkyl, or alkenyl of 3-4 carbons; provided, that only one of R 1 and R 2 is nitro; R = alkyl of 1-10 carbons, alkenyl of 3-7 carbons attached by a saturated carbon to N, cycloalkyl of 3- 5 carbons, propargyl, α -furylmethyl, α-tetrahydrofurylmethyl, α-thienylmethyl; and --(CH 2 ) n CN, --(CH 2 ) n COOH, --(CH 2 ) q OR 3 , --(CH 2 ) n COO (lower alkyl), and --CH(R 4 )(CH 2 ) p R 5 of up to 14 carbons, where n = 1- 6; p = 0- 5; q = 2- 6; R 3 = lower alkyl, phenyl, or lower alkylphenyl; R 4 = hydrogen or n-lower alkyl; R 5 = a hydrocarbyl group containing at least one ring of 3-9 carbons attached to alkylene by a ring carbon; provided, when p = O, the carbon attached to --CH(R 4 )-- is not a quaternary carbon; and its pharmaceutically suitable salts.
Claim 5
Dependent Claim
211 words
A compound of the formula: ##STR29## where R 1 and R 2 , the same or diffferent = hydrogen, lower alkyl, lower alkoxy, hydroxyl, fluorine, chlorine, bromine, 2,2,2-trifluroethyl, carboxyl, methoxycarbonyl, ethoxycarbonyl, N-methylsulfamyl, lower alkylcarbonyl, cycloalkylcarbonyl of 4-7 carbons, nitro, amino, acetamido, formyl, cyano, azido, fluoromethyl, difluoromethyl, formyloxime, acetyloxime, ##STR30## where R 6 is hydrogen, lower alkyl, or alkenyl of 3-4 carbons; provided, that only one of R 1 and R 2 is nitro; R = alkyl of 1-10 carbons, alkenyl of 3-7 carbons attached by a saturated carbon to N, cycloalkyl of 3- 5 carbons, propargyl, α -furylmethyl, α-tetrahydrofurylmethyl, α-thienylmethyl; and --(CH 2 ) n CN, --(CH 2 ) n COOH, --(CH 2 ) q OR 3 , --(CH 2 ) n COO (lower alkyl), and --CH(R 4 )(CH 2 ) p R 5 of up to 14 carbons, where n = 1- 6; p = 0- 5; q = 2- 6; R 3 = lower alkyl, phenyl, or lower alkylphenyl; R 4 = hydrogen or n-lower alkyl; R 5 = a hydrocarbyl group containing at least one ring of 3-9 carbons attached to alkylene by a ring carbon; provided, when p = O, the carbon attached to --CH(R 4 )-- is not a quaternary carbon; and its pharmaceutically suitable salts.
Claim 6
Dependent Claim
14 words
The compound of claim 3 where R 1 and R 2 are each hydrogen.
Claim 7
Dependent Claim
103 words
The compound of claim 4 where: R is alkyl of 1- 10 carbons, alkenyl of 3- 7 carbons joined to N through a saturated carbon atom, α-furylmethyl, --(CH 2 ) q --O (lower alkyl), --(CH 2 ) q --O--phenyl, or --CH(R 4 )(CH 2 ) p R 5 ; q is 2-6; p is 0-3; R 4 is H or CH 3 ; R 5 is cycloalkyl of 3 to 8 carbon atoms; cycloalkenyl of 3 to 8 carbon atoms; methylenecycloalkyl of 4 to 9 carbon atoms; polycycloalkyl of 7 to 9 carbon atoms; polycycloalkenyl of 7 to 9 carbon atoms; or phenyl.
Claim 8
Dependent Claim
14 words
The compound of claim 5 where R = n-alkyl of 2- 8 carbon atoms.
Claim 9
Dependent Claim
9 words
The compound of claim 6 where R is n-propyl.
Claim 10
Dependent Claim
9 words
The compound of claim 6 where R is n-hexyl.
Claim 11
Dependent Claim
9 words
The compound of claim 6 wherein R is n-heptyl.
Claim 12
Dependent Claim
9 words
The compound of claim 6 where R is n-pentyl.
Claim 13
Dependent Claim
20 words
The compound of claim 5 where R is alkenyl of 3-7 carbons, attached to N by a saturated carbon atom.
Claim 14
Dependent Claim
9 words
The compound of claim 11 where R is allyl.
Claim 15
Dependent Claim
53 words
The compound of claim 5 where R is --CH(R 4 )(CH 2 ) p R 5 , p is 0-3, R 4 is H or methyl; and R 5 is cycloalkyl of 3-8 carbons; cycloalkenyl of 3-8 carbons; methylenecycloalkyl of 4- 9 carbons; polycycloalkyl of 7-9 carbons; polycycloalkenyl of 7-9 carbons; or phenyl.
Claim 16
Dependent Claim
9 words
The compound of claim 13 where R is cycloalkylmethyl.
Claim 17
Dependent Claim
9 words
The compound of claim 14 where R is cyclopentylmethyl.
Claim 18
Dependent Claim
10 words
The levorotatory (-) isomer of the compound of claim 15.
Claim 19
Dependent Claim
10 words
The dextrorotatory (+) isomer of the compound of claim 15.
Claim 20
Dependent Claim
9 words
The compound of claim 14 where R is cyclohexylmethyl.
Claim 21
Dependent Claim
9 words
The compound of claim 14 where R is cycloheptylmethyl.
Claim 22
Dependent Claim
9 words
The compound of claim 13 where R is benzyl.
Claim 23
Dependent Claim
14 words
The compound of claim 13 where R is cycloalkenylmethyl of 5- 8 carbon atoms.
Claim 24
Dependent Claim
9 words
The compound of claim 21 where R is 1-cyclopentenylmethyl.
Claim 25
Dependent Claim
9 words
The compound of claim 21 where R is 3-cyclohexenylmethyl.
Claim 26
Dependent Claim
9 words
The compound of claim 13 where R is 2-exo-bi-cyclo[2.2.1]heptylmethyl.
Claim 27
Dependent Claim
9 words
The compound of claim 13 where R is 2-exo-bicyclo[2.2.1]hept-5-enylmethyl.
Claim 28
Dependent Claim
9 words
The compound of claim 13 where R is cyclopentylpropyl.
Claim 29
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceuutical carrier and an effective tranquilizing amount of a compound of claim 3.
Claim 30
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective tranquilizing amount of a compound of claim 4.
Claim 31
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective tranquilizing amount of a compound a claim 5.
Claim 32
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective tranquilizing amount of a compound of claim 15.
Claim 33
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective tranquilizing amount of a compound of claim 16.
Claim 34
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and an effective tranquilizing amount of a compound of claim 17.
Claim 35
Dependent Claim
19 words
A pharmaceutical composition comprising a suitable pharmaceutical carrier and and effective tranquilizing amount of a compound of claim 18.
Claim 36
Dependent Claim
19 words
A method of tranquilizing a mammal which comprises administering an effective tranquilizing dose of a compound of claim 3.
Claim 37
Dependent Claim
19 words
A method of tranquilizing a mammal which comprises administering an effective tranquilizing dose of a compound of claim 4.
Claim 38
Dependent Claim
19 words
A method of tranquilizing a mammal which comprises administering an effective tranquilizing dose of a compound of claim 5.
Claim 39
Dependent Claim
19 words
A method of tranquilizing a mammal which comprises administering an effective tranquilizing dose of a compound of claim 15.
Claim 40
Dependent Claim
19 words
A method of tranquilizing a mammal which comprises administering an effective tranquilizing dose of a compound of claim 16.
Claim 41
Dependent Claim
19 words
A method of tranquilizing a mammal which comprises administering an effective tranquilizing dose of a compound of claim 17.
Claim 42
Dependent Claim
19 words
A method of tranquilizing a mammal which comprises administering an effective tranquilizing dose of a compound of claim 18.
Claim 43
Dependent Claim
21 words
A method of producing analgesia in a mammal which comprises administering an effective analgesic dose of a compound of claim 3.
Claim 44
Dependent Claim
15 words
The compound of claim 3 where R 1 is amino and R 2 is hydrogen.
Claim 45
Dependent Claim
15 words
The compound of claim 3 where R 1 is cyano and R 2 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) | 1981-05-08 | 1981-11-07 | 1982-05-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-08 | 1985-11-07 | 1986-05-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-08 | 1989-11-07 | 1990-05-09 | $7700.00 | Window Closed / Lapsed |